Download the PDF [here] or Listen by clicking the play button below.

“Bearhug helped us hire all of our GTM function heads. Monthly sales have grown ~3x. Plus our team freaking loved working with them!”

Ivan Lvov
“Bearhug's a N of 1 at what they do. Any VC portfolio company with go-to-market hiring would be very lucky to work with them.”

Ryan Alshak
“I’ve recommended Bearhug to my board and will promote them to the other startup founders in my network. They've done an amazing job!"

Somya Kapoor
"Bearhug's approach was structured & methodical which helped us ferret out candidates we simply would not find through other means."

Sriram Ramachandran
"Bearhug helped us hire damn great department heads who've all built out strong teams. We’re growing 10% MoM & have expanded to 30 states!"

Maria Khokhlova
"Bearhug's in a category of its own. It's not even fair to compare them to other recruiters. Their process and work product blew me away."

Kourosh Zamani
"Bearhug found our winning candidate within 7 days. Towards the end, it felt like they were our own Chief People Officer."

Himanshu Gupta
“Working with Bearhug was worth every penny and every minute. I now have a new standard for how I'll recruit for all future hires.”

Robert Romano
"Of the 55 Executive Search Firms I've worked with, none had the follow-up, professionalism, thoroughness & enthusiasm as Bearhug Recruiting."

Richard DeFrancisco
“Bearhug's unwavering drive & persistence gave me the confidence they'd get the job done. We found an amazing "diamond in the rough!"

Aaron Elder
"Now I really know what it means to be a "great recruiter". I'm afraid there is an impossible gap between Bearhug and the rest."

Dmitry Korolev
"Bearhug's hiring window was solid. The process was solid. Our needs were met effectively which is why I’ve come back for all our GTM roles."

Rohit Gupta
"The experience with Bearhug was like a breath of fresh air. We hired a great new CEO and the way they serviced us was amazing.”

Josh Hailpern

The 27 Most Painful & Expensive Mistakes Tech Startup CEOs Make Before Launching an Executive Search (+ How to Avoid Them)

PLUS, how to cut executive hiring costs by up to $33K per search and pay as little as $2,500 for every other hire in your startup as you scale up.

When it comes to executive hiring, most startup CEOs don’t fail because they’re too early-stage, unproven, or can’t afford the talent they want.

They fail because they try and hire the right person at the wrong time (or too many people at once), set the search up wrong, or skip critical steps, unknowingly stacking the deck against themselves before the search even begins.

The result? A chain reaction of delays, mis-hires + $100K’s (if not $MM’s) in lost opportunity cost.

Most founders were never taught how to design and execute a true executive search strategy. They assume “recruiting is recruiting” and fall into the trap of running the same playbook no matter the level. A LinkedIn post here. An investor referral there. Ad-hoc tactics create inconsistent outcomes.

But every successful search runs on a structured, repeatable system, one that predictably attracts true A-players. Leaders with a 90% likelihood of achieving what only the top 10% of candidates can. Get the setup right, and you can land that leader in as little as 21 days.

The right leader, if targeted, positioned, and vetted properly, will run toward your challenges.

They’ll see opportunity in the chaos.

With the right strategy, you can persuade the top 10 % of the passive talent market to feel just as energized about joining your startup as they would about any headline-grabbing “rocket ship” you’re competing with for the best people.

That’s not theory, it’s the repeatable result we deliver for tech startup CEOs every day.

Below are 27 of the most painful and expensive mistakes startup CEOs make that derail their searches before they even begin, and how to sidestep each one.

Each aligns with the 3 pillars of our battle-tested Search Blueprint every CEO must master:

Structured Recruiting Workflow: Executive Search projects need to be laid out and project managed properly, or they’ll fail.
Comprehensive Sourcing Strategy: You must surface an accurate target list large enough to put the odds in your favor.
Role Positioning & Pitch: To poach the top 10% of the passive candidate pool, you’ve got to take an unconventional approach.

The following 27 mistakes are drawn from post-mortems of hundreds of executive searches and will point you toward a holistic solution you can implement before your next key hire.

They also lay the groundwork for the diagnostic conversation you should consider having with us ASAP.

Section I — Recruiting Setup Mistakes

1. Not locking in a target start date FIRST, in order to reverse-engineer the search project around.

2. Delegating a mission-critical hire to someone without the bandwidth or expertise to deliver.

3. Waiting until it’s “urgent” instead of pre-building talent pipelines & outreach campaigns in advance.

4. Assuming your network (or a job post) is enough to surface an A-player within your hiring window.

(Bonus: 🪜 The Talent Recruitment Ladder — The higher up you go, the smaller your candidate TAM, so be careful!

5. Failing to define the 10 most important questions (& answers) every candidate must address.

6. Not designing, assigning, and calendaring your internal interview loop.

7. Skipping pre-defining your reference-check strategy (who you’ll call, what you’ll ask, & when).

8. Not privately enrolling your trusted network to help promote senior-level opportunities.

9. Skipping the development of an internal “Search Blueprint Template” to use across the org.

10. Not pre-engineering a simple way to test candidates for the exact competencies you need.

(Case Study #1: 🔧 How a solid Search Blueprint transformed an impossible CPO search into a 57-day win.)

Section II — Sourcing Setup Mistakes

11. Failing to define a baseline of “red flags” that should instantly disqualify a candidate on paper.

12. Misaligning on which direct or adjacent industries are a bullseye (and which to avoid).

13. Targeting candidates at companies at the wrong stage (pro tip: only go 2 to 3 stages ahead).

14. Not pre-defining appropriate titles or experience levels (“too junior” vs. “too seasoned”).

15. Ignoring tenure requirements (i.e. the “4 in 10” rule, your best de-risking filter).

16. Not defining your ideal candidate’s career journey from college to today (DO NOT SKIP).

17. Failing to spell out the state of the tech stack & playbook, why it’s the way it is, and what they’ll inherit.

18. Failing to source at least 50 A-player profiles before outreach begins.

(Case Study: 🏗 How a structured search saved an almost failed CEO handoff & fueled $100M growth.)

Section III — Pitch & Positioning Mistakes

19. Not fully articulating your contrarian views on product–market dynamics and your early GTM instincts.

20. Failing to tell your CEO story and strategic narrative in full to align with and activate your ideal candidate’s “why.””

21. Giving candidates too little context about the company’s current state before they start your interview loop.

22. Hiding the hard parts of the job or internal challenges (A-players will be drawn to the hard stuff).

23. Glossing over the history of the role or department, and why this role exists today.

24. Failing to share granular level detail about how and why customers buy your product + your GTM motion in depth.

25. Not painting a vivid picture of the real company culture, and how things actually get done early-on.

26. Not defining explicit 90-day and year-one outcomes before the search begins.

27. Assuming a larger, more established, or “specialized” 3rd party search firm automatically means better results.

Section IV — Bearhug’s Holistic Recruiting Solution

Two Parallel Tracks: “Master Platter” (Executive Search) & “Top-of-Funnel Talent” (non-exec hires)
Diagnose First, Price Second: How our 2-step custom solutioning process works
Why Bearhug: How our performance partnership guarantees pre-defined results at every stage or you won’t pay a penny.
How to book your “Discovery Diagnostic” call to explore fit.

Appendix & Resources

Watch our intro video to learn about our practice
Step into the Hallway of Hugs to see recent feedback
Explore our new Services Menu and list of Recent Placements

Section I — 🎣 The Most Painful & Expensive Recruiting-Setup Mistakes

Mistake #1: Not locking in a target start date to reverse-engineer your search strategy & schedule around.

It sounds obvious, but every time we ask a CEO, “What’s your target start date for this leader?” the answer is almost always some version of “Anytime in the next three to four months.”

It’s an innocent mistake, so we clarify, “No, your target start date.”

Most founders were never taught that the single biggest risk in executive hiring isn’t finding great candidates, it’s aligning your timing with their timing.

You’re usually trying to pull a top performer out of another high-growth company that’s a few stages ahead of you, someone who’s doing the best, most important work of their career. And you’re asking them to walk away from it to come build something new with you.

These people aren’t job-hunting. They’re likely ignoring every average recruiter’s outreach.

Meanwhile, inside your company, you’re under pressure to hit growth milestones on schedule, and the gap this role represents is directly limiting that progress. That’s why timing is everything: the moment your readiness and their availability intersect is the only window where a hire can actually happen.

As we’ll cover later, this starts with building your target list first, before outreach, so you can activate that full market at once, batch your outreach, and run the entire process in one or two tight 30-day waves. That approach keeps momentum high, candidates warm, and the decision cycle aligned with your timeline and theirs.

We put this mistake first for a reason. It’s the foundation for everything else. And while this rule doesn’t apply as strictly to non-executive roles that rely on active candidates, it’s absolutely critical for senior hires where you’re courting the top 10% of the passive market, the leaders who can most directly influence your startup’s growth, valuation, and ultimately, its liquidity event.

🧭 Pro Tip: You simply can’t run an effective search without anchoring to a clear start date. Saying “We’ll just hire them when we find the right person” might sound reasonable, but it’s one of the most dangerous mindsets a CEO can hold when time-to-scale is the enemy.

Every month of delay compounds the cost.

Mistake #2: Delegating a mission-critical hire to someone without the bandwidth or expertise to deliver.

This is another completely innocent mistake. One almost every early-stage CEO makes at some point.

At this stage, you’re juggling everything: investors, fundraising, product, GTM, customers, and hiring.

If you’re lucky, you’ve got a capable COO or Chief of Staff who steps in to run the executive hiring workflow. But that handoff, while practical, introduces real risk. If that person lacks deep recruiting expertise, or if they’re already underwater with competing priorities, the odds of a great outcome drop fast.

Even once you hire an internal recruiter, it’s easy to assume they can handle everything from SDRs to C-level hires. In reality, executive recruiting and non-executive recruiting are two entirely different disciplines, with different networks, skill sets, processes, and candidate motivations. Expecting one person to do both well is like asking your head of growth to also own finance and product management.

To save time or money, many founders turn to contingency or hourly recruiters, but that creates a new set of problems.

Contingency recruiters often juggle 15–20 searches at once and only get paid if a placement closes, which means your search competes for attention with dozens of others. You’re not paying them to focus, and focus is exactly what you need for a senior hire.

Hourly recruiters have the opposite issue: they get paid by the hour, not for outcomes, so there’s no real incentive to move fast or dig deep.

The point is: if this is a mission-critical executive hire, don’t delegate it to someone without the time or expertise to do it right. Either own it yourself, or make sure the person leading the search has dedicated capacity and real experience running executive-level searches.

And even if you delegate, you still need to stay involved in the middle, specifically when it’s time to review the short list (or “slate”) of qualified, interested, and available candidates. That’s when your judgment matters most: deciding who’s worth putting into your internal interview loop based on both their profile on paper and the business case the recruiter, internal or external, has built around each potential candidate.

🧭 Pro Tip: You can, and should, delegate up to 90% of the process. But you can’t skip the most important part: co-authoring the Search Blueprint and Scorecard, weighing in on the slate, being the first person candidates meet internally before passing them to the rest of your team, and then re-engaging at the end when it’s time to vet the finalist with your board and advisors. That’s the leverage point where your leadership has the biggest impact, and where great searches turn into great hires.

Mistake #3: Waiting until it’s “urgent” instead of pre-building talent pipelines & campaigns in advance.

There are two kinds of CEOs, just like there are two kinds of people when it comes to health. Some are proactive. They work out, sleep well, drink water, get regular bloodwork (shoutout Function Health), and make small adjustments before small issues become big ones.

They invest early in prevention.

Others take the reactive path. They’ll deal with things when they become a problem. No judgment, life happens. Some people beat the odds either way. But in business, especially in early-stage startups, being reactive about talent almost always catches up to you.

Recruiting isn’t a one-time event. It’s an ongoing system.

If you don’t yet have a simple way to track people you might want to hire someday, start now.

Even if it’s just for the roles that report directly to you.

When you’ve built those lists and filled out your Search Blueprint and Scorecard, you’ll be able to spin up a new search in a single one-hour meeting, with everyone aligned, roles defined, and candidates already in motion.

That’s what proactive leadership looks like. Just don’t forget what we covered in Mistake #1. None of this works without a clearly defined target start date.

🧭 Pro Tip: Reactive hiring costs time, momentum, and morale. Proactive hiring compounds.

Mistake #4: Assuming Your Network (or a Job Post) Is Enough to Surface an A-Player Within Your Window.

This one’s deceptively simple, and almost every founder gets burned by it.

You lean on your network, throw a post on LinkedIn, maybe even hire a contingency firm to “help with flow.” It feels productive… until you realize the best candidates never even saw the role.

Here’s the truth: that approach can work for mid-level hires or when luck’s on your side. But at the executive level, it’s a coin toss at best.

Even if you’ve already got a decent list, a mix of investor intros, past candidates, or people your team admires, it’s still just a list. Without the right Search Blueprint to shape who belongs on it and why, you’re flying blind.

🧭 Pro Tip: You can build a list anytime. But building the right list, one anchored to the right sourcing strategy, workflow, and pitch, is what separates lucky hires from predictable results.

💸 Sidebar: Why “Posting and Praying” Fails

Most CEOs treat recruiting like sales: post a role, generate leads, close a deal.

But that model breaks the higher up the org chart you go.

The best executives aren’t leads; they’re passive candidates doing the best work of their lives and not looking to switch jobs.

They don’t browse job boards or fill out applications either.

They get hunted, and carefully courted, by skilled professionals.

That’s where most searches go off the rails: CEOs use the same playbook for every role.

But different levels of talent live in different ecosystems and respond to entirely different approaches.

Here’s the simple four-level framework we use to explain this shift: The Talent Recruitment Ladder

🪜The Talent Recruitment Ladder

Different levels of talent live in different ecosystems and require different recruiting approaches. The higher up you go, the more targeted, personalized, and strategic your method must become.

🧩 Level 1 – Low to Mid-Level (Recurring) Roles

These are repeatable, high-turnover, or process-driven positions, roles you’ll need to fill again and again as your company scales.

Job platforms like Indeed, LinkedIn Jobs, and Glassdoor work here because these candidates are actively looking. Cast a wide net and use automation or AI to filter quickly and maintain a steady pipeline. Because these roles recur frequently and follow consistent hiring patterns, the strategy should emphasize systemization, automation, and repeatability, optimizing for speed, efficiency, and long-term cost control rather than one-off searches.

(Note: This is where having the right infrastructure, or partnering with someone who can run it for you until you’re ready to bring it in-house, quietly pays for itself many times over. Pro Tip: During our diagnostics call offered below, make sure to ask us about our “Top of Funnel Talent” offering. It can solve many of your non-executive level hiring needs with very little effort, for less than you could on your own.)

⚙️ Level 2 – Specialized Roles

These are niche positions that require technical depth or domain expertise, the “operators” who turn strategy into execution. They’re typically found in specialized communities like GitHub, Product Hunt, marketing forums, or industry Slack groups.

They’ll move for the right opportunity, but only if your pitch speaks directly to their craft and values. To attract this group, you need insider fluency, an understanding of where they gather, what they value, and how to frame opportunity in language they’ll be attracted by and respect.

(Note: Generic outreach won’t cut it. “Top of Funnel Talent” can often work here as well.)

🎯 Level 3 – Leaders

These are emerging senior operators, the people who may or may not yet hold VP, Head of X, or Director titles but already think and perform like they do. They’ve been in the rooms and on the teams where growth happens, helped shape the playbook, and are now ready and excited to lead.

But they won’t be browsing job boards. They respond to direct, credible outreach from a peer or someone who speaks their language, through platforms like LinkedIn, X (Twitter), or at in-person industry events or inside niche leadership communities.

For most Seed and Series A CEOs, this is the sweet spot for your functional heads. Proven C-level executives often aren’t willing to step into the chaos of an early-stage startup, the ambiguity, the lack of infrastructure, and the personal financial risk. But these next-up leaders, the ones who’ve just lived through the growth story your company is about to start and helped lead, are ready.

They’re often the number twos, the lieutenants, or the high-velocity individual contributors who lead others without title and helped build the machine (and were maybe even more instrumental than their boss). They will always carry a chip on their shoulder and a hunger to prove they can lead the next one.

When positioned well, they’ll jump at the chance to own a function (Head of Sales, Head of Marketing, Head of Product, Head of CS, Head of Finance, etc.), especially if your story, equity, and timing align. To reach them, you need a narrative-driven approach that weaves together positioning, pitch, and timing.

(Note: This is where Bearhug’s Search Blueprint will separate amateur CEOs from true professionals on the recruiting front and give you access to talent who’ll grow into the role instead of waiting to hire them later.)

🏆 Level 4 – Executives

These are seasoned C-level executives who’ve led one or more major business functions at meaningful scale, owning functional P&L, building and optimizing teams and systems, and delivering repeatable outcomes. They bring strategic depth, maturity, and true executive presence. More than anything, they add horsepower to the engine you’ve already built, accelerating growth and strengthening execution.

When it makes sense: You generally pursue this caliber of leader at or beyond Series B, when the business has real traction, strong PMF, mountains of data, and a foundation ready to scale. The goal is to attract a proven operator who’s already taken a company from roughly $30M to $100M and has the appetite (and energy) to do it again. That’s no small task. Many executives at this level will shift into advisory or portfolio careers, but a select few will be motivated by the right challenge, team, and equity.

This is the “Growth” zone in Bearhug’s Early and Growth Stage practice. These leaders don’t need a perfect situation to plug into, far from it. But they do need strong product-market fit, reliable data, foundational infrastructure, and a brand with traction. With those ingredients in place, they can make an immediate impact. They’ll often rearchitect teams, processes, and strategy, bringing in new people and ideas to help the business break through its next plateau and unlock $100M+ in revenue scale.

How they engage: Executives at this level might reply if you or your board reach out directly, but that approach rarely produces the best outcome. The smarter play is to work through a trusted talent partner who’ll represent you discreetly and build curiosity before revealing the specific opportunity.

At Bearhug, we’re able to enter the conversation without naming your company upfront, gather real insight on timing, compensation, and motivations, and identify whether there’ll be a genuine fit before bias or comparison sets in. Because these leaders know we represent multiple venture-backed companies, they’re far more open and candid than they would ever be with you or your advisors.

That early trust allows your talent partner to shepherd the process end to end, perfectly positioning your opportunity to fit their exact situation while surfacing hidden concerns early and stitching the deal together step by step all the way through to close. We can sell you better than you can sell yourself, because we carry third-party credibility and neutrality. However, at this level, the total candidate universe is often tiny (sometimes as few as a dozen humans on earth) and is easily alienated by a mismatched pitch or clumsy process. Getting it right the first time isn’t optional; it’s essential.

What the search requires:

Precision targeting (tight market map, functional track records that match your stage and goals).
Narrative orchestration (why this mandate, why now, why them; customized business cases).
Flawless execution (every message, name, and touchpoint counts).

(Note: This is where relationships, reputation, and craft matter most. Boutique retained partners like Bearhug map the market from scratch, handpick leaders, and persuade the ones others can’t reach, while running a transparent, milestone-aligned process. Big-brand firms can deliver too, but expect layered teams, slower cycles, higher fees, and time-based billing. Choose the model that aligns with outcomes, not overhead.)

⚠️ Bonus Mistake: Using Level 1 tactics to find Level 4 people — or vice versa.

Remember: A $350K VP won’t reply to your Indeed ad, and a $50K marketing coordinator won’t be poached by a headhunter. Match your method to the level, and your results will transform.

Click Here To Review Our New "Holistic Recruiting Solution"

Mistake #5: Failing to define the 10 most important questions (& answers) every candidate must address.

This might be one of the simplest, yet most transformative, exercises a CEO can do before launching a search. Out of every possible question you could ask a candidate throughout the entire interview cycle, what are the 10 most important ones that every finalist must answer before you’d feel confident making an offer?

Imagine your team has a shortlist of pre-qualified candidates, all interested, available, and aligned on the basics. If you could only ask 10 questions across that slate, which ones would truly reveal whether each person is right for the job? And just as importantly, what would great, good, and deal-breaker answers look like for each?

Most CEOs never take the time to define this. They rely on ad-hoc conversations and “gut feel,” hoping alignment magically appears across interviewers. The result is inconsistent evaluations, scattered notes, and post-interview confusion about who’s actually best suited for the role.

When we run searches at Bearhug, this exercise happens toward the end of the intake process, after the Search Blueprint is complete and we’ve clarified the role, outcomes, competencies, and DNA traits. With all that context, identifying the 10 most important questions becomes almost effortless.

🧭 Pro Tip: This is the moment when most founders have an “ah-ha” realization: success in recruiting, just like in every other part of life, starts with asking the right questions and aligning the team on what good answers really look like. Once that’s in place, the process flows so much faster. True alignment starts with shared questions, not shared opinions.

Mistake #6: Not designing, assigning, and calendaring your internal interview loop.

Most early-stage CEOs underestimate how fragile a hiring process really is. They think an interview loop means a few conversations strung together in logical order:

“I’ll meet them first. If I like them, I’ll send them to my number two. If that goes well, we’ll meet together, maybe loop in a few team members, do a presentation, get board buy-in, and make the offer.”

Sounds clean. But without structure, sequencing, and time blocking, that plan collapses fast.

If every participant in the loop hasn’t been briefed on the overall search strategy, what their specific role is, what questions they’re responsible for, and how their input will weigh in the final decision, you’re setting up chaos disguised as collaboration.

What ends up happening when things are done this way?

Interviews overlap or go out of order.
Everyone asks the same questions.
No one owns the candidate experience.
Scheduling conflicts stall momentum.
The best candidates quietly disengage.

By the time you realize what’s happening, your top choice has gone cold, accepted another offer, or decided your process feels “off.”

This is one of the biggest silent killers in executive hiring: a poorly orchestrated loop signals internal dysfunction, and A-players pick up on it immediately. The moment a search starts to feel ad hoc, it stops feeling attractive.

That’s why, at Bearhug, we pre-define every step of the loop before launch. Who’s in it, what their purpose is, what questions they’ll cover, how long each step should take, and when each calendar block should already be held. Everyone involved understands that the search is a batched, time-sensitive workflow, not an open-ended sequence of “let’s find time.”

🧭 Pro Tip: When the loop runs this way, you maintain velocity, signal competence, and keep every candidate warm and engaged. It’s not bureaucracy; it’s choreography. And it’s the difference between landing your top pick and watching them disappear to a competitor.

Mistake #7: Skipping pre-defining your reference-check strategy (who you’ll call, what you’ll ask, & when).

This is where many otherwise great searches blow up. CEOs ask, “How do we really vet them?” and then wing it. References get rushed, back channeled, or skipped (risky for you and unfair to the candidate).

The two biggest hazards:

Ad hoc backchannels (too early): Quietly “asking around” about passive candidates before outreach has occurred, or mid-loop, can leak, jeopardize someone’s current job, and poison the well. Unless handled by a trusted third party with real discretion, don’t do it.
Last-minute scramble (too late): Waiting until offer time with no plan leads to delays, shallow calls, or skipping references entirely because momentum feels fragile (and no one likes bad news).

Do this instead (simple, repeatable playbook):

Timing: After your internal team votes “proceed to hire,” request the reference list (names, contact info, context) but explain they need to alert the people, and that you will not make the calls until after the offer stage and before resignation.
Who: Ask for six names: two above (their two most recent managers), two beside (peers or cross-functional partners), and two below (direct reports). Always point to recent relationships tied to relevant outcomes.
Ownership: Have a neutral, trusted operator (your retained talent partner or a single executive sponsor) run a structured set of calls to keep consistency and candor high.
Use of signals: Decide in advance which standardized questions you’ll ask, plus one or two custom ones to pressure test specific areas for each candidate. Align on how you’ll interpret mixed feedback, what qualifies as a deal breaker, and who has final decision authority. Always keep a backup finalist warm and ready in case the preferred candidate falters.
A players don’t flinch: When you’ve been aligned from the start about who influenced them (mentors, managers, peers, and reports), true A players actually welcome this step. Hesitation at the reference request stage is a major red flag, no matter the reason. It usually signals one of three things: they’re not truly closed and may be using the process to trigger a counteroffer, they’re not fully bought in enough to signal to their network that they’re serious about making a move, or there’s a story you haven’t heard yet that deserves a closer look.
Why this matters (beyond validation): Great reference work does more than confirm facts. It tells you how to onboard and coach the hire, what to watch or mitigate, who they may attract to follow them, and sometimes even surfaces customer or partner leads. Done right, it’s the single most leverage-rich step.

🧭 Pro Tip: Don’t improvise references. Pre define the strategy (who, what, when, and who runs it) or you invite leaks, delays, bias, and preventable mishires. This is where a discreet third party earns their keep: keeping candidates safe, getting unvarnished truth, and preserving momentum to close.

Mistake #8: Not privately enrolling your trusted network to help promote senior-level opportunities.

Most CEOs underestimate how powerful their personal network can be, and how easily it can backfire if used poorly. The difference comes down to intentionality and message control.

Too often, founders casually mention a search in a Slack group, a portfolio thread, or a LinkedIn post, hoping word of mouth will surface someone great. The result? Dozens of unqualified intros, scattered messaging, and a diluted brand impression of the role. The smarter move is to strategically enroll your network privately, with precision, timing, and a consistent story.

Once you’ve signed off on your Search Blueprint, the sourcing strategy, recruiting workflow, and written pitch distilled into a one-page Scorecard, package it into a polished external version. Then share it, quietly and intentionally, with a select circle of trusted peers, advisors, investors, and community members. Ask them to privately forward it to one or two specific people they believe fit the profile or would know someone who does.

We do this for our clients and refer to it as the “Persuasive Position Brief,” which is a clear, magnetic narrative that frames the role, the challenge, the outcomes, and the upside. When this strategy is done right, it transforms your network into a distributed recruiting engine, without hardly lifting a finger.

Everyone tells the same story. Everyone sells the same opportunity. And because the message is consistent, the results compound, turning passive talent into active candidates who are already pre-sold before you ever speak with them.

It’s also one of the fastest ways to raise the bar across your entire ecosystem. A world-class position brief doesn’t just attract A players; it makes your peers rethink how they pitch roles too. That’s the ripple effect of doing this right.

🧭 Pro Tip: Don’t rely on luck, noise, or ad hoc posts to activate your network. Build the asset, control the message, and privately enlist allies who’ll carry it with care. Done well, it can replace weeks of sourcing effort with one smart email and a thoughtful piece of collateral that tells a compelling story.

Mistake #9: Skipping the development of an internal “Search Blueprint Template” to use across the org.

Every successful executive search starts with a Blueprint, a structured, repeatable framework that defines how your company sources, recruits, positions, and evaluates senior talent.

At Bearhug, we’ve refined ours over a decade and hundreds of executive searches. It’s a living, evolving system, built from post-mortems on what works, what fails, and why most startups struggle to land the right leader fast.

The Blueprint is built on four core pillars:

Sourcing Strategy: How and where you identify and prioritize target candidates.
Recruiting Strategy: How the search is structured, sequenced, and managed (from first outreach to final offer).
Positioning and Pitch: How the role is framed, differentiated, and sold to the market.
Scorecard: The measurable definition of success once you’ve met your finalists.

Every mistake outlined in this report ties back to one of those four pillars. Founders who operationalize this framework inside their company turn it into a Search Blueprint Template used across the entire organization that every hiring authority can rely on to hire better, faster, and with far less drama and friction.

The Scorecard is the capstone. It distills everything into a single one-page decision framework that makes hiring objective instead of emotional.

It should include:

A clear mission for the role, its “why.”
The five key outcomes this person must deliver in their first 12 months.
The five core competencies they must demonstrate.
The five DNA traits that determine culture fit and long-term alignment.

That is 15 criteria. When your team uses that Scorecard to evaluate finalists, discussions become data driven. Everyone speaks the same language. Debriefs get shorter. Decisions get faster. Confidence skyrockets.

By the time you’ve narrowed the field to one to three finalists, the Scorecard becomes your compass, guiding reference checks, offer design, and final stakeholder alignment. It is also what allows your board or advisors to quickly validate the hire without redoing the entire process.

🧭 Pro Tip: Most hiring pain comes from skipping the Blueprint and flying blind. When you build this system once, and reuse it across your organization, you eliminate 90 percent of the chaos that derails senior hiring and create a scalable foundation for every future search, regardless of function or seniority.

(Pssst! Want access to our internal template to build your own? We originally gave it away to a private group of portfolio founders from one of our favorite VC firms during a Masterclass we hosted back in August 2023. It has evolved a lot since then, but the core framework is still there, and it’s yours if you want it. The catch? You’ll need to watch the Masterclass and follow the instructions inside to unlock it.) 👉 Get it [here].)

Mistake #10: Not pre-engineering a simple way to test candidates for the exact competencies you need.

This is where your Scorecard becomes real, translating theory into behavior you can actually observe.

Most CEOs rely on interviews and references to assess skill, which means they’re mostly testing communication, not competence. The best predictor of performance is still the simplest: watching someone do the work.

But there’s a catch. You can’t ask a senior operator, especially a passive candidate, to “do free work” for you mid process. That’s insulting and can backfire.

The key is to design a lightweight, inspiring, two to three hour challenge that mirrors a real scenario they’d face in their first few weeks on the job, something that gets them excited to show what they can do, not defensive about being tested.

It should arrive at just the right moment in your interview flow, typically after three touchpoints, when they’re emotionally invested and can see themselves succeeding in the role. You hand them a simple, well written one pager that makes them think:

“Hell yeah, this actually sounds fun. This is a problem worth solving.”

The goal isn’t to judge perfection. It’s to watch how they think, how they communicate under light pressure, how they structure a solution, and how they’d collaborate with your team to move fast without perfect data.

A great test aligns with the top five outcomes and competencies from your Scorecard and gives you a front row seat to what life with this person would feel like after they’re hired.

Here are some examples you might consider building on:

💼 Sales Leaders

Review a real or anonymized rep discovery call recording, then coach the “rep” (played by the CEO or Head of Sales) live, demonstrating how they develop talent.
Run a mock pipeline review using a sample CRM report (deal values, time in stage, rep ownership). The committee plays the sales team.
Build and present a short go to market mini strategy for a new ICP or territory (30 minute prep, 15 minute share).

📣 Marketing Leaders

Evaluate a recent campaign’s performance data and suggest the next three experiments to scale growth.
Draft a sample launch narrative or positioning refresh based on your company’s product page.
Outline the first 90 days of marketing org optimization: what they’d do, in what order, and why.

💰 Finance Leaders

Review a mock P&L or cash flow snapshot, then walk through how they’d identify and prioritize areas to fix or optimize.
Conduct a 20 minute budget variance or forecasting scenario review with the CEO, surfacing key levers.
Present how they’d implement a board reporting cadence and metrics dashboard for scale up readiness.

💡 Product Leaders

Analyze a customer feedback set and outline how they’d prioritize the next sprint.
Conduct a mock roadmap review with the CEO or CTO, showcasing tradeoff thinking and communication style.
Run a feature triage exercise, picking what to ship, what to kill, and why.

🧭 Pro Tip: The best candidate tests feel like a preview of working together, not a pop quiz. You’re not evaluating whether they get it right. You’re seeing how they think, collaborate, and lead.

🔧 Case Study: ServiceUp — CPO in 57 Days

How a well built Search Blueprint turned a complex executive search into a 57 day success story.

Before diving into the sourcing pitfalls, here’s a quick look at how getting the setup right can transform the entire search outcome.

When ServiceUp, a Series B Autotech marketplace backed by PeakSpan Capital, came to us, they needed a Chief Product Officer to help scale from roughly $20M to $100M+. On paper, the obvious move was to hunt within Autotech. But once we built the Search Blueprint, the data told a different story.

We discovered that the strongest fit wasn’t in the same lane at all. It was in adjacent industries like healthcare, where AI native product leaders had already solved similar operational and scaling challenges. That insight completely reframed the search.

Within 57 days, ServiceUp had its new CPO, a builder leader who had scaled AI driven marketplaces before and could now do it again in a new vertical.

Lesson: When your setup is precise, with sourcing strategy, recruiting workflow, and positioning all in sync, your results compound. The right map leads to the right mountain.

👉 [Read the full ServiceUp CPO Case Study & Press Release]

Click Here To Review Our New "Holistic Recruiting Solution"

Section II —🔎 The Most Painful & Expensive Sourcing-Setup Mistakes

Mistake #11: Failing to define a baseline of “red flags” that should instantly disqualify a candidate on paper.

Every CEO has an internal filter for who feels like a “fit.” The problem is that filter usually lives only in their head. When it comes to sourcing, most leaders never stop to define what should be an instant DQ on paper. They rely on instinct, but instinct doesn’t scale, and it doesn’t align a team.

For example:

There are companies you would avoid (those with toxic cultures, shady reputations, or investor conflicts).
Or patterns you would flag (too many short stints, constant industry hopping, or unusual titles or changes).
Or background gaps (irrelevant degrees, function zig zags, or resumes that scream “too generalist”).

The list goes on. And while these rules may be obvious to you, they’re invisible to everyone else helping with your search, from your internal team to your external partners. That is why the first step in any sourcing strategy should be to get those red flags out of your head and onto paper.

Once you do, everyone filtering candidates can operate from the same baseline, saving hours of wasted sourcing time and ensuring your funnel fills with aligned, high quality profiles.

At Bearhug, we always document these disqualifiers early in the Search Blueprint. It sharpens the sourcing list, strengthens the Position Brief, and even helps candidates self select out before ever being brought forward, which means the ones who do engage are already pre aligned in a lot of key ways.

🧭 Pro Tip: When your red flags are defined upfront, sourcing stops being random guesswork and starts becoming pattern recognition with purpose.

Mistake #12: Misaligning on which direct or adjacent industries are a bullseye (and which to avoid).

Here’s where we get into the inside baseball of sourcing, the step that determines who you’ll actually talk to, and ultimately, who you’ll hire. Clearly, the crux of the entire recruiting process.

Most CEOs understand, at least in theory, that great hires often come from other high growth environments, the companies they admire, compete with, or hope to emulate. That’s the right instinct. But where things go sideways is in the industry mapping phase, when the team never slows down to define which industries are truly in bounds, and which should be ruled out entirely.

And the biggest unforeseen error?

Many CEOs delegate early list building to a cheap overseas researcher or virtual assistant without giving them a strategy first, hoping they’ll “pattern match” their way to the right profiles. The result? Dozens of hours wasted reviewing irrelevant candidates and a bloated list that may look impressive for one reason or another, but won’t actually standardize your list on the right criteria in the right order.

Before you ever hand sourcing off, do the strategic thinking yourself (ideally with a talent partner):

“Which industries reliably produce the kind of leaders you want, and which don’t?”

Here’s how we break it down inside the Search Blueprint:

Direct industries: Companies selling similar products and or selling to similar customers with comparable go to market motion and complexity (ideally similar price points and cycle lengths).
Adjacent industries: Same muscle groups, different sport. With thoughtful reasoning, these can double or triple your viable talent pool and unlock some super interesting candidates who will excel.
Avoid industries: Just as critical. Define the no fly zones such as conflicting investors, outdated models, misaligned cultures, or totally different operating rhythms.

Only after this foundation is set should you add secondary filters such as location, size, funding stage, founding year, or employee count to further narrow it down. At Bearhug, we’ve benchmarked hundreds of searches and found the sweet spot for executive level company market mapping almost always falls in the range between 200 and roughly 800 source companies.

That may sound like a lot, but it’s the difference between luck and certainty. Just as you need a large enough candidate list to hit your desired outcome (more on that in a moment), you need a sufficiently broad company universe to ensure you’re seeing the full market and not missing the one leader who could change your company forever.

When you do this right, sourcing becomes a precision sport. Your target list almost builds itself, your team stays aligned and confident the search will stay on track, and your odds of success multiply.

🧭 Pro Tip: Never outsource the thinking. If you want quality out of your sourcing partners (internal or external) or tools, give them a strategy first. A clear bullseye saves you from a thousand wasted arrows. Think of it like surface area: the bigger and cleaner your market map, the luckier you get.

Mistake #13: Targeting candidates at companies at the wrong stage (Pro Tip: Go two to three stages bigger.)

One of the most common and costly mistakes founders make is building a sourcing list with no calibration around company stage.

The result? A Frankenstein mix of profiles, brilliant on paper but totally mismatched in practice.

Here’s the truth: candidates don’t just bring skills; they bring stage experience, the invisible muscle memory of having solved problems at a specific size and speed. If you ignore that, you’ll hire someone who is either out of their depth or bored out of their mind.

For early stage startups (Seed to Series A), the smart move is almost always to reach up and target leaders currently at Series B or C companies who have lived through the next level of complexity you are about to face. They’ve seen what good looks like, built systems that scale, and can help you skip painful first time exec mistakes. Sometimes that extends into Private Equity backed environments if the leader’s roots are founder led and they have stayed close to the front lines. (Timing matters; too long in PE and that startup muscle starts to fade.)

For growth stage startups (Series B to C), it’s the reverse problem. Pulling from Seed or A stage organizations rarely works; the gap in structure, resources, and scale expectations is just too wide. That said, as a backup strategy if your top target pool runs thin, it can be a smart place to poach from. Many of those leaders are ready to escape the “feet to the fire, no resources” grind for something more stable where they can actually apply what they’ve learned. Just make sure their career trajectory shows consistent wins that align directly with your next chapter; otherwise, you’ll inherit burnout, not leverage.

The core rule: Hire people who have already solved for your next chapter, not your current one.

That is how you collapse learning curves, avoid false starts, and accelerate through your next growth inflection point.

🧭 Pro Tip: When mapping your sourcing strategy, label every target company with its funding stage, team size, and growth velocity. If you can’t clearly explain why a candidate’s current environment mirrors where your company will be in 12–24 months, you’re probably fishing in the wrong pond.

Mistake #14: Not pre-defining appropriate titles or experience level (“too junior” vs. “too seasoned”).

When sourcing, clarity beats volume. One of the easiest ways to waste weeks is by chasing profiles that look senior on paper but don’t truly match your target level of experience.

Titles are one of the most visible and most misleading on page attributes. They need context to mean anything.

Go back to the Talent Recruitment Ladder concept we covered earlier. Before you even start building lists, get explicit about which rung you are recruiting from:

Are you targeting a true exec, someone who has already led at scale and can bring pattern recognition from the next stage up?
Or are you looking for an up and coming leader who will grow into that executive seat over time?

That distinction alone changes your entire sourcing strategy and your odds of success.

But here is where many searches go wrong: title inflation. In today’s market, C level titles are handed out like candy, especially at early stage companies. It’s not unusual to see a “CPO” or “CRO” at a seed stage startup with five people and no product market fit. That is not a deal breaker, but it is a yellow flag. Unless they are a co founder, a C level title before Series B should trigger curiosity, not confidence.

The fix is to zoom out and review the full trajectory of each candidate’s career:

How have their titles progressed across companies and over time?
What stage and size were those companies during their tenure?
Did they move laterally or upward, and what might that say about their readiness for what is next?

Example: If someone was a VP of Product for four years at one company, then moved to another of similar size and stayed in the same title for five more years, ask why. Lateral moves aren’t always bad, but they are signals you will need their help to interpret.

This is where building a simple ranking system pays off. Create weighted criteria for key on page attributes like title, progression, tenure, and company size. Research the growth rate and trajectory of each company during the candidate’s tenure, and capture quick notes for follow up when you speak with them. Then score each profile, stack rank your top 50, and focus your time there.

At Bearhug, we often review more than ten thousand profiles before narrowing the field to the roughly 50 leaders we will actively headhunt, using a structured, custom scoring system we build collaboratively with each client. When it comes to executive hiring, there is no step more important than building the right list. Your outcome will always mirror who is on it, so make sure it is the right people, or you will spend months chasing the wrong ones.

Remember: titles are just labels; context is the truth.

🧭 Pro Tip: Early title inflation is not always a red flag, but it is never a green one. Always correlate the title with company stage, team size, and outcomes delivered.

Mistake #15: Ignoring tenure requirements (the “4 in 10” rule — your best de-risking filter).

When you are sourcing senior talent, there is one simple pattern that instantly separates stable builders from serial jumpers: the 4 in 10 Rule.

Look at the past 10 years of a candidate’s career. How many companies have they worked at?
If the answer is more than four, it is almost always a pass unless they are absolutely exceptional in every other way.
It is not a rigid law, but it is one of the best de risking filters you can apply early in your sourcing process.

Over a decade, four or fewer moves typically signals commitment, resilience, and the ability to stay long enough to deliver real outcomes. More than that often reveals impatience, burnout, or a pattern of running from challenges instead of through them.

If you have mapped your market correctly (pulling from both direct and adjacent industries), your pool should be large enough that you can apply this standard confidently without starving your list of great talent.

Here is how to think about it:

4 companies in 10 years: ✅ Green zone. Ideally, it is 2 to 3. Healthy movement, proven staying power.
5 or more companies in 10 years: ⚠️ Yellow zone. Only advance if context is clear and exceptional.
7 or more companies in 10 years: 🚫 Red zone. Skip. Too volatile, too risky.

There are a few critical nuances to layer on top:

Do not chase people too early in their current role. If they have been at their current company for less than two years, skip them. They are likely not ready to move, and even if they are, it is rarely for the right reasons. The best leaders want to finish what they start. Pursuing them before they have crossed that two year threshold (ideally the three to four year mark) almost always leads to wasted effort or worse, a mis hire you could have easily avoided. It is also tough to poach top performers before they have finished vesting. Equity schedules are a powerful anchor; most strong operators will not seriously entertain a move until they have earned the next tranche or completed their initial grant. Trying to pull them earlier rarely works, and if it does, you are likely disrupting someone’s unfinished arc rather than attracting a leader who is truly ready for their next chapter.

The sweet spot is three to five years. That is typically long enough to prove impact, but not so long that they have gone stagnant. The best leaders either move up or move out every few years, and their resumes show it.

Watch for the other extreme. Someone who has been in the same role or same company for eight to ten years without real upward progression can be just as risky as someone who hops constantly. Unless they have taken on significantly new scope or led through major inflection points, that is usually a sign of comfort, not growth.

At Bearhug, we bake these tenure rules directly into our sourcing models. We will often review more than ten thousand profiles and automatically score tenure as a key input alongside title, company size, and stage alignment. It is one of the simplest ways to protect against bad fit hires before you ever start outreach.

🧭 Pro Tip: Build the “4 in 10 Rule” and a “2 Year Minimum” into your scoring system. The result? Stronger candidates, fewer false starts, and a shortlist of leaders who actually finish what they start.

Mistake #16: Not defining your ideal candidate’s career journey from college to today.

Every great hire has a powerful career arc, and so should your ideal candidate.

Before you write a job description or build a target list, take time to map the career narrative of the kind of person who would be at the perfect inflection point to step into this role today.

This exercise is not about finding someone with the exact background you sketch out. It is about identifying the archetype, the journey that would make someone ideally equipped to fill your current gap and carry the company through its next one to three stages of growth.

We do this with every client we partner with, and in about half of our searches, we uncover not one but two viable career arcs, different paths that can lead to the same kind of high impact leader. Seeing those archetypes side by side almost always sharpens the search and opens doors you would not have known to look behind.

Here is how to do it:

Start at the beginning. Imagine what the ideal person might have studied in college (or their early life experience if they skipped it). Whether or not they finished their degree matters less than whether they have shown a lifelong pattern of starting and finishing, joining teams, and leading initiatives.
Trace the through line. What is the logical sequence of experiences, roles, titles, industries, and projects that would naturally lead them to being great at this job right now?
Spot the forks in the road. In many cases, there are two archetypes worth tracking, for example one product leader who grew up in design versus another who came from engineering. Map both journeys and source against them in parallel.

When you later meet candidates, you will use this imagined narrative as a pattern matching framework, a lens to guide your curiosity. You can even build it into your interview questions:

“You studied X in college, then went into Y and Z early in your career. Tell me how your thinking evolved along the way, what drew you to each move, and how those decisions shape how you lead today.”

This single prompt often unlocks more truth than an entire behavioral interview. It tells you how a candidate thinks, what drives them, how self aware they are about their journey, and whether they are still growing or just repeating the same loop.

At Bearhug, we have found this to be one of the most powerful ways to refine sourcing and interviewing at the same time. It brings the art and science of executive search together, helping you recognize not just the resume fit but the narrative fit behind it.

🧭 Pro Tip: Do not just read resumes, read stories. When you can see how someone’s choices connect, you can predict how they will handle what comes next.

Mistake #17: Failing to spell out the state of the tech stack & playbook, why, and what they’ll inherit.

It is surprising how few CEOs can clearly describe the current state of their tech stack or functional playbook during early search setup. Most assume candidates will figure it out later, but this is one of the biggest missed opportunities in both sourcing and attraction.

Every function runs on a stack plus a system of plays. Top tier candidates will immediately want to know:

What tools and systems are in place today?
Why were they chosen?
Are they working, broken, or due for an overhaul?
And what exactly will I inherit?

This matters more than you might think. The best executives do not want to walk in blind; they want to know whether they will be fixing, optimizing, or accelerating what is already in motion. If you cannot clearly answer that, you will lose credibility fast, and the best candidates will quietly disengage.

Each function has its own version of this:

Marketing: Campaign calendar, attribution model, CRM and automation stack, creative rhythms.
Sales: Pipeline management system, enablement tools, sales process (the playbook), compensation plan logic.
Product: Roadmap cadence, sprint methodology, collaboration tools, release process.
Finance: Systems stack (ERP, FP and A, reporting), accounting rhythm, investor communication cadence.

The key is to document and define the state of these systems early, before the role hits the market. Be explicit about what is working, what is broken, and what is open to change. Signal whether the new leader’s mandate will be to rebuild, refine, or run the existing setup, and make that part of your positioning.

This also sharpens your sourcing. When you are building your Market Map, note which technologies each target company uses. It helps identify candidates who already know your core tools and can ramp faster, or those who have led successful migrations from the platforms you want to leave behind.

At Bearhug, we use this as a critical input during our Blueprint process. When clients can clearly describe what is under the hood and why, it dramatically improves sourcing precision and messaging resonance. Candidates immediately self select in or out, saving weeks of wasted conversations and ensuring whoever you hire knows exactly what they are walking into.

🧭 Pro Tip: Transparency is a magnet. Top candidates do not expect perfection; they expect honesty. Spell out the current state of your tech stack and playbook, and you will attract builders who want to solve real problems, not caretakers looking for comfort.

Mistake #18: Failing to source 50+ A-player profiles before outreach begins to stack the odds in your favor.

If there is one sourcing mistake that quietly kills more searches than any other, it is this one: going to market with a list that is too small.

Too many CEOs (and even internal recruiters) convince themselves that a shortlist of 10 to 20 names is enough to get started. It is not. That is a wish list, not a search strategy.

Worse, a list that small makes it impossible to run your search like a true project, with defined stages, tight timelines, and coordinated handoffs. Without enough volume, the process drags. Candidates go cold, your team loses focus, and momentum stalls. Suddenly what could have been a six week sprint turns into a six month slog, not because the talent was not out there, but because the foundation was not built to sustain the pace.

The truth: until you have staged 100 to 500 potential profiles and then methodically scored them down to the 50 to 75 best fits for aggressive outreach, you are guessing, not recruiting.

Why does this matter so much? Because no matter how compelling your pitch or how deep your network, only a fraction of your total addressable talent market will ever be the right fit to begin with, and even fewer will be willing to take your call or consider your specific opportunity.

Let’s do the math:

Out of your top 50, you will typically connect live with about half (via phone, email, or social).
Of those 25 conversations, about half again will be truly qualified, available, and interested.
That leaves you with 10 to 12 engaged candidates worth deep dive interviews, exactly the number you need to produce a three to four person finalist slate and a successful hire.
This is why list depth matters more than list speed. The bigger and better your staged list, the more accurate your pattern matching, and the higher your probability of landing a true A player.

To do this right, score every staged profile against clear, objective criteria such as titles, company stage, tenure, performance signals, and industry adjacency. Only then can you confidently narrow the field to the 50 to 75 candidates who truly deserve your (or your talent partner’s) time and attention.

And here is the kicker: your warm network will never be enough.

The odds that your next executive hire is sitting inside your LinkedIn connections or your investors’ contact list are near zero. You have to go beyond who you know, to the total market of who is right.

At Bearhug, we review more than ten thousand profiles per search to arrive at those same 50 to 75 names, because that is the only way to truly isolate the top 10 percent of any market. Once you see this system in action, and the outcomes it produces, you will never go back to the post and pray approach again.

🧭 Pro Tip: The quality of your hire is directly proportional to the quality and quantity of your research. You do not find A players by starting small. You earn them by starting big and narrowing hard.

🏗️ Case Study: TraceAir CEO Succession Pivot

How a five-year partnership and a structured search process turned a delicate CEO succession into a $100M growth story.

Before diving into the positioning & pitch setup mistakes, here’s what happens when long-term trust meets methodical execution.

Bearhug first partnered with TraceAir when it was a scrappy seed-stage startup fresh out of 500 Startups. Over the next five years, we helped the founders assemble their entire leadership team — from their first marketing hire to key functional leaders — as the business scaled rapidly.

But by the time TraceAir hit its next inflection point, the founders made a rare and humbling admission: the company had outgrown them.

Together with their board, they decided it was time to bring in a new CEO to guide the next phase of growth — a high-stakes move made even more complex by ongoing acquisition interest.

Then, midway through the process, came the twist: the sitting COO realized he wanted the job.

After participating in the interview loop and seeing the caliber of external candidates we’d surfaced, he recognized that with his deep institutional knowledge and history with the company, he might be the best person to lead it forward.

Rather than resist the shift, we helped the founders and board evaluate the move objectively — and pivoted the search to find the complementary leader the new CEO would need beside him.

Fortunately, one of the top candidates we’d previously disqualified in late-stages for being “too much of a COO” for the original CEO brief turned out to be a perfect fit. We re-engaged him, repositioned the offer, and closed the hire.

That candidate — Joel LeBlanc — has since become instrumental in driving TraceAir toward its $100M+ milestone. Meanwhile, former COO Ivan Lvov stepped up to become President and, ultimately, CEO, as the founders transitioned into advisory roles.

Lesson: The most complex searches don’t just test your process — they test your flexibility. When handled with honesty, humility, and a clear framework, even major pivots can produce the perfect outcome.

👉 [Read the full TraceAir CEO → COO Case Study & Press Release]

Click Here To Review Our New "Holistic Recruiting Solution"

Section III 🎯 The Most Painful & Expensive Pitch-Setup Mistakes

Before you ever go to market, you need a clear, compelling way to sell the story, in writing, behind your company and the role. And that starts with you, the CEO.

The truth is, experienced and even up and coming leaders want to understand far more about how you think than you realize. The best ones want to get inside your head, but they are often hesitant to ask early on, sometimes even during the interview process.

They will often wait until after they are hired to truly see the market, the mission, and the opportunity through your eyes, the level of detail they need to properly evaluate the opportunity and ultimately succeed in the role.

That is why having a partner who can pull that story out of you and translate it into language that moves top tier operators can make or break your search.

At Bearhug, we have spoken with thousands of executives. We know how they think, the questions they will ask (and the ones they will not, the ones we can ask for them to benefit both sides), and what instantly turns them off. And that is a good thing. The more both sides know about each other upfront, the stronger and faster the match.

Most CEOs are exceptional at selling. It is how they have raised capital, won customers, and convinced the world their vision matters. But this kind of selling is different. You are not pitching investors or prospects; you are asking another high performing human to bet their career on your trajectory, to get in the cockpit with you.

That is why even great communicators struggle to do it alone. It is human nature. It is easier to champion a product or team than to sell the idea of working directly with you. So whether you are running the search internally or with a third party talent partner, make sure someone takes the time to fully interview you, pulling the gold from your brain and shaping it into a long form narrative that makes the top 10 percent of the candidate pool lean in before you have ever spoken with them.

We have broken down the most common and costly mistakes CEOs make in their pitch and positioning setup into the following seven buckets:

Mistake #19: Not fully articulating your contrarian views on product–market dynamics and GTM instincts.

In the eyes of the top 10 percent of executive candidates, every CEO worth joining has a contrarian worldview, a belief that something others think is crazy might actually be right. It is what separates the exceptional from the average.

But most CEOs never articulate that worldview through the lens of recruiting another executive to join them. They assume their conviction is obvious, that candidates will just get it. They will not. At least not fully. If you want the best talent, you need to clearly express your contrarian belief in the context of the specific role you are hiring for, showing how that executive can help you prove it right.

The best leaders, the ones you actually want to hire, crave insight into how you think.

They want to know:

What do you believe about your market that others get wrong?
What hard lessons shaped that belief?
Where have your GTM instincts paid off or backfired?
How has the game surprised you along the way?

When you share these things openly, it builds trust, credibility, and energy. It helps candidates decide if your version of reality aligns with theirs, and when it does, it is electric.

If you are not giving candidates this level of access to your thinking, you are asking them to take a leap of faith on a one dimensional story.

🧭 Pro Tip: The strongest pitch decks we co write with founders always include a section called The Contrarian Bet, a one paragraph explanation of the belief that drives the company. It is where 90 percent of emotional buy in happens.

Mistake #20: Failing to tell your CEO story in full, to align with & activate the ideal candidate’s “why.”

If Mistake #19 is about your worldview, this one is about your origin story, the story that explains how you became the kind of CEO someone would want to follow.

Every top tier candidate, especially at the executive level, wants to know who they are building alongside. And the more aligned their “why” is with yours, the faster the trust forms. That is why you need to treat your CEO story like an essential piece of recruiting collateral, not a casual anecdote you wing mid interview.

Here is the secret: your story is not just for candidates. It is for your team, your board, and yourself. When you take the time to script it, from the early seeds of what shaped you, to the pivotal decisions, the near misses, and the moments of doubt, you create an emotional through line others can see themselves in.

We tell CEOs all the time: you are asking candidates to share their story and put it on the line for you, so you owe them yours in return.

When you weave in the personal alongside the professional, the mentors who shaped you, the failures that hardened you, the convictions that carried you, people do not just understand what you have built. They understand why you built it and why it matters.

That is where real alignment happens, when someone hears your story and quietly says to themselves, “I want to be part of that next chapter.”

🧭 Pro Tip: Just as you map a candidate’s career journey from college to today, do the same for yourself. This story sharing exercise will not only make you a better interviewer, it will make you a more relatable leader.

Mistake #21: Giving too little context about the company’s current state before interviews (the real story).

Top candidates are not just evaluating what the company does. They are evaluating what they are walking into.

One of the biggest mistakes founders make is playing it too safe when describing the company’s current state. They think they are protecting themselves by holding back. In reality, they are handicapping their own pitch.

You do not need to give away trade secrets or drop your full data room on day one. But if you want elite executives to engage meaningfully, you have to give them a clear, candid picture of where things actually stand, the good, the bad, and the still in progress.

Think of this as your State of the Union. How is the business performing? What are the key wins and setbacks? What is the current runway, the state of the team, and the major inflection points ahead? You are not writing a PR statement. You are writing the truth, in context.

Handled well, this type of transparency builds credibility and trust faster than any sales pitch ever could. The right candidates lean in when they feel they are being treated like insiders, not prospects. The wrong ones opt out, and that is a gift.

At Bearhug, we have seen this play out hundreds of times. When we ask CEOs for both their sales deck and fundraising deck during intake, there is often a pause, part hesitation and part realization. But once we translate those materials into a tailored candidate narrative, the difference is night and day.

Candidates arrive to first interviews already understanding the market, the mission, the metrics, and the moment they are being hired into.

The result? First conversations that feel like third ones. Deeper chemistry, faster decisions, and far fewer surprises later on.

🧭 Pro Tip: The goal is not to reveal everything. It is to reveal enough for candidates to evaluate the opportunity with the same depth you are evaluating them. Transparency does not scare A players. It attracts them.

Mistake #22: Hiding the hard parts of the job or internal challenges (A-players are drawn to the hard stuff).

A players do not run from hard problems. They self select into them. If your pitch hides the mess, you will attract optimists and tire kickers, not the true operators and leaders you need.

The move is radical candor: name the friction, scope it, and show the path to win. Give candidates a clear picture of what they will inherit and what they are expected to change. Done right, this filters out the wrong fits and energizes the right ones.

Frame the truth across every dimension:

Product and roadmap: What is working, what is half built, what is being deprecated. Non negotiables versus open to rewrite.
Team they will inherit: Current strengths, gaps, and performance variance. Who is on the bubble. Where you need upgrades.
Cross functional reality: How Sales, Marketing, Product, Success, and Finance actually work together. Decision rights; where escalation lives.
Board and advisors: Expectations, pressure points, pet theses, cadence, and how success is really judged.
Customers and partners: ICP clarity, win or loss truths, churn patterns, channel dependencies, where support is breaking.
Market context: Tailwinds, headwinds, pricing pressure, new entrants, regulatory or macro risks you cannot ignore.
Competition: Where rivals truly outshine you in product depth, brand, distribution, or capital, and your counter play.
Culture and operating system: What behaviors get rewarded versus tolerated. Meeting load, planning rhythm, how decisions stick.
Leadership gaps: Where you, the CEO, need this hire to balance you. What you will stop doing the day they start.
Execution constraints: Runway, hiring freezes, tech debt, tool sprawl, data quality, the real limits they must manage.

How to share it (without oversharing):

Package a one page Hard Things Brief. Three columns: What is hard, Why it is hard, How we will attack it (with you).
Use ranges and directionality instead of sensitive absolutes (for example, “gross retention in the low 80s, trending up with X initiative”).
Pair each truth with a credible first 90 days mandate so it reads as a solvable challenge, not a confession.
Deliver the brief pre interview via a trusted partner (or under light NDA) to invite thoughtful dialogue, not defensiveness.

🧭 Pro Tip: Honesty accelerates fit. The wrong candidates self deselect. The right ones start problem solving out loud. Your first conversation feels like week three on the job, and your odds of a great hire go up immediately.

Mistake #23: Glossing over the history of the role or department (or why this role exists now).

Top candidates do not just ask what the job is. They ask why this job, now. If you skip that story, you create doubt and force them to reverse engineer the truth via backchannels.

Tell the origin story plainly (pick the scenario and lean in):

Net new role (Seed or Series A): Why now? What did founder led or IC led get you? Where did it stall? What must this leader own on day 1, day 30, and day 90? What do you want them to keep versus reinvent?
Backfill after a departure: What worked, what did not, and what you will not repeat. Was it stage mismatch, scope creep, culture friction, results? What success looked like when it worked.
Confidential replacement: Define the business need without naming the person. “We are evolving from X to Y; here is the gap we must close.” Keep it respectful, specific, and forward looking.

What great context includes (without oversharing):

Timeline: When the seat was created, key pivots, leadership coverage, interim decisions.
Mandate shift: How the mission, metrics, and scope changed (or must change) and why.
Interfaces: Who they will inherit, where the team is strong or fragile, and cross functional fault lines.
Lessons learned: Three things you would do differently and three you would absolutely repeat.
Why now: Trigger event (growth, churn, new product, board ask, market shift) and urgency window.

How to package it:

Create a one page Role History Brief with four blocks: Then → Now → Why It Changed → What the Next 12 Months Require.
Pair it with a Scorecard (mission, top 5 outcomes, top 5 competencies, top 5 DNA traits) so the story flows into evaluation.
Tone guidelines (steer between PR and gossip):
Be candid, not careless. Facts over blame. Patterns over personalities.
If it is a confidential backfill, speak in systems (“handoffs broke between Sales and CS”) rather than people.
Always connect the past to a clear path forward that the new leader can own.

Why this works: It de risks the decision for elite candidates. You signal maturity, self awareness, and a solvable challenge. The wrong people self select out. The right ones start drafting their first 90 day plan on the spot.

🧭 Pro Tip: End your brief with a single sentence: “If you had been in this seat the last 12 months, what would you have done differently, and what would you keep?” Great operators light up; tire kickers fade out.

Mistake #24: Failing to share how and why customers buy your product + your GTM motion in depth.

This one trips up even the most experienced CEOs. It feels dangerous, like revealing too much. But withholding the story of how you go to market does not protect you; it limits who will join you.

Top candidates, especially proven GTM, product, and finance leaders, do not just want to know what you sell. They want to know how it moves through the market: who buys, why they buy, how they find you, how long it takes, and what breaks along the way.

That is not trade secrets. That is context, and it is what allows great operators to think like owners before they have even joined.

If your edge is real, it cannot be copied overnight. Your execution muscle, relationships, and compounding insight are the moat. So share what is working, what is not, and what you suspect might be off but cannot yet prove. The honesty is magnetic.

What to unpack in your GTM story:

The customer journey: Where discovery happens, what triggers action, and why prospects stall.
Your current motion: Inbound to outbound ratio, deal cycles, conversion rates, and key leverage points.
Pricing and packaging: What has been tested, what is stable, and what is ready for experimentation.
Channels and partnerships: What is driving new logos versus expansion, and where coverage is thin.
Enablement and operations: Tech stack, data quality, visibility gaps, and what the next level requires.
Competitor dynamics: Who you actually bump into, how often you win, and why.

The goal is not to hand over a playbook. It is to open a conversation.

By laying it all out, you invite elite candidates to think alongside you. The best ones will instantly start ideating. And when you batch those finalist interviews close together, you will find yourself pattern matching their perspectives, hearing what each would tweak, double down on, or scrap.

By the time you make an offer, you will not just know who is right for the role. You will have sharpened your own strategy.

🧭 Pro Tip: The more candid your GTM narrative, the more magnetically you will attract the right leader for the role. Transparency is not a liability. It is a litmus test.

Mistake #25: Not painting a vivid picture of the real company culture (i.e. how things actually get done).

Culture is not a tagline. It is the lived experience of how work happens day to day, the rhythms, habits, and unspoken rules that shape performance. Yet most CEOs describe it with vague clichés such as fast paced, collaborative, or mission driven. Those words tell a candidate nothing.

A players want to know what it is really like to work inside your walls, the texture of daily life, how decisions are made, and what kind of environment they will be stepping into. Skip the gloss and give them a mental movie they can picture themselves inside.

Start here, what candidates actually want to know:

Environment: What does it feel like to be there? Open floor plan or quiet focus spaces? Plants, windows, chatter, music? Is it jeans and sneakers casual or sharp collar formal?
Rhythm: What does a real day look like? When do people arrive, break, leave? Are there sacred focus hours or constant collaboration?
Social fabric: Do people eat lunch together, celebrate wins, hang out after work, or keep boundaries tight?
Communication style: Slack threads, email chains, whiteboard sessions, or spontaneous hallway decisions?
Learning cadence: Are there all hands or training rituals such as roadmap sessions, product deep dives, or market education?
Hierarchy: Can anyone walk into the CEO’s office, or does everything flow through layers? How much autonomy versus alignment?
Decision style: Consensus driven or decisive and fast? Who actually makes the call when there is friction?

The more you can describe these details in plain language, the faster candidates self sort. Some will be turned off, which is good. Others will feel an instant spark of recognition: “This feels like my kind of place.”

This is not fluff. It is risk reduction. Culture mismatch is one of the top three causes of failed executive hires, and it is completely preventable.

🧭 Pro Tip: Do not write your culture story like a random HR person would, just checking boxes or recycling whatever has been pinned to the wall since 2018. Write it like a travel guide. Make candidates feel what it is like to work there before they ever step inside.

Mistake #26: Not defining explicit 90-day and year-one outcomes before the search begins.

This one is simple, and deadly when skipped.

Most CEOs enter a search with a vague sense of what success feels like but not what it looks like. They assume they will figure it out once they meet the right person. But without clearly defined outcomes, you are not hiring against reality. You are hiring against chemistry.

The fix is to define two horizons before the first candidate is ever contacted:

The First 90 Days, The Integration Window: This is not about deliverables; it is about velocity, alignment, and proof of fit. What will they learn, decide, fix, or build by Day 90? Who do they need to influence or hire? What early indicators will show they are gaining traction?
The First Year, The Value Window: What tangible business outcomes must exist 12 months in? Think measurable metrics such as revenue, retention, margin, product velocity, team growth, operational maturity, or whatever needle this role must move. Then layer in qualitative outcomes, the behavioral shifts or cultural changes you are counting on this leader to drive.

Here is the part most CEOs miss: this should be a two way negotiation, not a test. You are not handing down commandments; you are aligning expectations. Tell candidates upfront what you hope, want, and need. Then ask what they would commit to and where they would push back. The resulting dialogue is gold. It reveals how they think, what they prioritize, and how they handle tension long before the offer stage.

Skip this step, and you will default to vague scorecards, hand wavy interviews, and post hire disappointment. Define it early, and every part of the process — sourcing, interviewing, evaluation, even compensation — gets sharper.

🧭 Pro Tip: Replace the tired 30 to 60 to 90 day plan exercise with a simple two column document: Our Expected Outcomes versus Their Proposed Plan. Use it as a living alignment tool throughout the process. The best hires will help you rewrite it before they are even hired.

The Most Painful & Expensive Mistake (External Recruiters!)

Mistake #27: Assuming a larger, more established, or “specialized” firm automatically means better results.

Size does not equal quality, and specialization does not guarantee performance. Yet it is one of the most common and costly assumptions CEOs make when choosing a search partner.

Here is the reality: most big name firms divide every project across multiple layers such as researchers, associates, and partners, each handling a small slice of the process. What you get is bureaucracy disguised as horsepower. It slows everything down and turns the search into a game of telephone.

Even worse, many rely on static databases rather than building a fresh market map from scratch around your unique needs. You are not getting a custom hunt. You are getting a rerun.

Then there is the billing model. Large firms typically collect fees early, tied to time or milestones, not performance. When the search gets tough, or you are not the client paying the biggest retainer that quarter, attention drifts. You end up paying more for a slower, less personalized process and a watered down slate.

Sure, you could roll the dice with a contingency firm or an hourly recruiter, but their incentives do not align with securing the best possible leader inside your critical hiring window. They win by filling any seat fast, not the right seat well.

The real cost of that misalignment: delays, failed searches, and mis hires that set your business back months and can burn hundreds of thousands (if not millions) in lost opportunity.

🧭 Pro Tip: The best firms do not sell access. They sell certainty. Look for partners who start from zero every time, run a transparent process, and tie their success directly to yours.

Click Here To Review Our New "Holistic Recruiting Solution"

Section IV — Bearhug’s Holistic Recruiting Solution

Let’s be blunt: the biggest mistake of all, Bonus Mistake #2, is not even on the list above.

It is waiting too long to start.

Most CEOs do not realize they have already lost the first 90 days of their search before it even begins. By the time they finally decide to hire their next key executive, their pipeline has gone cold, the team is buried in firefighting, and the board is breathing down their neck.

The smartest CEOs front load the strategy and avoid the scramble.

That is exactly what Bearhug’s Holistic Recruiting Solution was built for: a flexible, diagnostics first system that adapts to your stage, hiring volume, and growth horizon.

We run two parallel tracks:

🎯 1. The Master Platter (Executive Search, Retained Project Model)
For small or critical leadership pools, the high stakes searches where precision, discretion, and persuasion matter most. Each search starts with a blank canvas: custom market mapping, narrative positioning, and hands on headhunting led by a Partner (never delegated).

⚙️ 2. Top of Funnel Talent (Non Exec, Subscription Model)
For non executive, recurring, multi location, or high turnover roles, we build repeatable pipelines that run 24/7, delivering a steady flow of pre qualified and pre vetted candidates ready for you when you need them.

Pricing starts as low as $2,500 per role and flexes based on volume, turnover, repeatability, and geographic scope.

The hook: we stay embedded, so when hiring needs surface, your pipeline is already warm.

🧠 Diagnose First, Price Second

Just like a great mechanic, we do not quote before inspection.

Every engagement begins with a free 30 Minute Discovery Diagnostic, the first step to clarify your goals, workflow, and 3 to 12 month headcount plan. From there, we will co design a custom recruiting roadmap, followed by a tailored proposal that fits your growth stage, urgency, and complexity.

There is no one size fits all approach, only precision fit solutions.

💡 What You Will Gain

Certainty: A proven system that delivers the right hire, fast.
Clarity: A roadmap that aligns your entire team before outreach.
Continuity: A partner who evolves with you as your needs scale.

🔧 Time for a Recruiting System Check Up

Every early and growth stage CEO tunes their product and GTM engine, but rarely their hiring engine.

Start with your free 30 Minute Discovery Diagnostic, and we will assess where your recruiting workflow may be costing you time, talent, or traction.

Why Bearhug

Most firms sell access to a database.

We sell certainty, that the right leader will be found, fast, and will change your company forever.

Bearhug Recruiting is a boutique executive search firm and trusted partner to early and growth stage Environmental Technology and Enterprise Software startups scaling from roughly $3M to $100M+.

Every great company you admire was built on one truth: competitive advantage is a who, not a what.

Unlike traditional firms that recycle tired networks or bill you regardless of outcome, Bearhug starts every search from scratch, mapping the market, handpicking leaders from the top 10 percent, and persuading the ones everyone else cannot reach.

Our proprietary Search Blueprint and Scorecard System combines structured intake, tight calibration, and real time transparency to deliver hires that are not only faster (2.5 times the industry average) but stronger.

Each partner runs no more than three searches at a time, ensuring high touch collaboration and a true white glove experience for both clients and candidates.

We remove upfront risk through milestone based billing, flexible pricing under our Easy Button MSA, and a Performance Partnership Guarantee that ties our success directly to yours.

The result: nearly every client becomes a repeat client. VC firms introduce us across their portfolios, both pre funding and post funding, and candidates often describe the process as the most thorough and thoughtful recruiting experience of their careers.

Bearhug does not just fill roles. We help founders unlock $100M+ in revenue scale by building executive dream teams that transform companies.

The Real Difference

Does it make sense now why we charge what we do?

This is not the kind of logic you will ever get from an hourly recruiter, a contingency shop, or someone buried in HR. You will only hear it from people who have taken the punches, the ones who have been in the trenches trying to rip the top 10 percent of talent out of the hottest companies on the planet and convince them to join a startup with risk, ambiguity, and fire everywhere.

That takes finesse. It takes obsession. It takes knowing how to read people, push just enough, and close the deal without breaking trust. That is what we do every single day.

When you land a real A player, one of the few who can actually bend the growth curve, they will 10x, 50x, even 100x your investment in us.

So no, we are not expensive. We are the difference between a company that scales and a company that stalls.

And here is the kicker: our internal systems are so dialed in and repeatable that we can also drop our pricing to the floor for your less critical but still essential roles. We will blend our sourcing channels with your internal resources, calibrate the right level of vetting, and give you a one stop talent engine that cuts costs, improves efficiency, and crushes your competition.

Bearhug is not here to compete on price. We compete on outcomes.

🐻 We Fish. We Dish. And We Deliver Results Worth Bragging About. 🐟

P.S. We could have easily listed another hundred mistakes we see in the field, but the team voted to slip in one last bonus, so technically, there are 30.

⚠️ Bonus Mistake

Believing some shiny new AI tool will magically research, source, reach out, pre qualify, pre sell, write up, schedule, and even sign the top 10 percent of the passive talent pool to your team.

Sounds incredible, and we agree.

It is why we are heads down building fully automated, end to end AI systems for higher volume, low to mid level roles, bringing better economics and faster outcomes for our clients.

But here is our current hot take: at the executive level, the true leaders, the generals moving the chess pieces, will always require a thoughtful, strategic courtship to lift their heads and consider something new.

That kind of engagement cannot yet be automated. And even when it can, few Boards, still led by humans, will trust recruiting their next C suite this way. The best candidates certainly won’t.

Appendix & Resources

👉 Watch our intro video to learn about our practice [here]

👉 Step into the Hallway of Hugs to see recent feedback [here].

👉 Explore our full Services Menu and list of Recent Placements [here]

👉 Download the PDF version of this page [here] or “listen” to the NotebookLM version (our favorite method) [here].

Click Here To Review Our New "Holistic Recruiting Solution"

We Fish & We Dish™

"Your level is above 99% of recruiters because of the obsessive detail you go through to truly understand both the candidates and the role. Most firms say they go deep, but Bearhug actually does. That’s why we got the outcome we wanted, in the timeframe we needed."

Brett Moyer
"Bearhug’s process was absolutely thorough. From market coverage to real-time visibility, nothing was left unexamined. We landed the perfect person for the moment. 10/10."

Brett Carlson
"The Bearhug team is one of the top executive search firms in the nation. They have a very unique perspective on building and scaling companies and I highly recommend their work!"

Spencer Dusebout
“I want to commend the Bearhug team for being such excellent partners to our entrepreneurs and the larger PeakSpan team. We really appreciate and value our relationship with you!"

Phil Dur
“Bearhug helped one of our portfolio companies hire almost their entire C-level team. That business has scaled from 1 to 20M+ over the last 4 years. They are an amazing partner for exec hiring for series A/B startups!””

Anton Fedorov
"I’ve worked with dozens of search firms, and Kraig and the Bearhug team are truly something special. They put more thought into their work than almost anyone I’ve met in business."

Jay Potter
“Kraig and the Bearhug team are one of the best startup recruiting firms I have ever met.”

Gaurav Manglik
"Kraig, we are thrilled to formally finish the process. Congratulations on your helping us get an amazing new executive to our company!"

Vangelis Mihalopoulos
"Having seen Bearhug from both sides, as a candidate & client, their approach is unmatched. Radical transparency and hands-on coaching delivered results that felt like a miracle."

Jon Kerry-Tyerman
“Bearhug’s outreach stood out immediately — specific, contextual, and focused on real impact. The process was collaborative, transparent, and the most thoughtful I’ve ever experienced."

Amit Shrivastava
“Bearhug’s approach was refreshing — transparent, knowledgeable, and focused on adding value from the start. Their approach turned a high-stakes role into a smooth, confidence-building experience.”

Nick Ezzo
"Bearhug is the recruiting partner high-growth businesses need — experienced, transparent, and realistic about what’s possible in senior searches. They bring urgency and deep preparation to every step."

Colin Parker
"Bearhug does things differently. The process was thoughtful, transparent, and executed with a level of rigor and insight I didn’t expect."

Doug Brown
"I was initially skeptical, but Bearhug quickly proved different — down-to-earth, empathetic, and thorough. They exceeded all expectations and delivered a great outcome for both sides.”

Matt Fox
"Bearhug’s process was extremely structured, efficient, and effective. Unlike anything I’d ever experienced. The level of detail and organization gave me total confidence at every step."

Jason Murante
"Getting to know the Bearhug team through such a thoughtful, structured process was a standout experience. Any high-growth startup needing specific executive hires should expect not just results, but a process that makes candidates want to join."

Walter Rowland

“Bearhug helped us hire all of our GTM function heads. Monthly sales have grown ~3x. Plus our team freaking loved working with them!”

“Bearhug's a N of 1 at what they do. Any VC portfolio company with go-to-market hiring would be very lucky to work with them.”

“I’ve recommended Bearhug to my board and will promote them to the other startup founders in my network. They've done an amazing job!"

"Bearhug's approach was structured & methodical which helped us ferret out candidates we simply would not find through other means."

"Bearhug helped us hire damn great department heads who've all built out strong teams. We’re growing 10% MoM & have expanded to 30 states!"

"Bearhug's in a category of its own. It's not even fair to compare them to other recruiters. Their process and work product blew me away."

"Bearhug found our winning candidate within 7 days. Towards the end, it felt like they were our own Chief People Officer."

“Working with Bearhug was worth every penny and every minute. I now have a new standard for how I'll recruit for all future hires.”

"Of the 55 Executive Search Firms I've worked with, none had the follow-up, professionalism, thoroughness & enthusiasm as Bearhug Recruiting."

“Bearhug's unwavering drive & persistence gave me the confidence they'd get the job done. We found an amazing "diamond in the rough!"

"Now I really know what it means to be a "great recruiter". I'm afraid there is an impossible gap between Bearhug and the rest."

"Bearhug's hiring window was solid. The process was solid. Our needs were met effectively which is why I’ve come back for all our GTM roles."

"The experience with Bearhug was like a breath of fresh air. We hired a great new CEO and the way they serviced us was amazing.”

The 27 Most Painful & Expensive Mistakes Tech Startup CEOs Make Before Launching an Executive Search (+ How to Avoid Them)

Table of Contents

Section I — 🎣 The Most Painful & Expensive Recruiting-Setup Mistakes

🪜The Talent Recruitment Ladder

🔧 Case Study: ServiceUp — CPO in 57 Days

Section II —🔎 The Most Painful & Expensive Sourcing-Setup Mistakes

🏗️ Case Study: TraceAir CEO Succession Pivot

Section III 🎯 The Most Painful & Expensive Pitch-Setup Mistakes

The Most Painful & Expensive Mistake (External Recruiters!)

Section IV — Bearhug’s Holistic Recruiting Solution

Why Bearhug

The Real Difference

🐻 We Fish. We Dish. And We Deliver Results Worth Bragging About. 🐟

⚠️ Bonus Mistake

Appendix & Resources

We Fish & We Dish™

"Your level is above 99% of recruiters because of the obsessive detail you go through to truly understand both the candidates and the role. Most firms say they go deep, but Bearhug actually does. That’s why we got the outcome we wanted, in the timeframe we needed."

"Bearhug’s process was absolutely thorough. From market coverage to real-time visibility, nothing was left unexamined. We landed the perfect person for the moment. 10/10."

"The Bearhug team is one of the top executive search firms in the nation. They have a very unique perspective on building and scaling companies and I highly recommend their work!"

“I want to commend the Bearhug team for being such excellent partners to our entrepreneurs and the larger PeakSpan team. We really appreciate and value our relationship with you!"

“Bearhug helped one of our portfolio companies hire almost their entire C-level team. That business has scaled from 1 to 20M+ over the last 4 years. They are an amazing partner for exec hiring for series A/B startups!””

"I’ve worked with dozens of search firms, and Kraig and the Bearhug team are truly something special. They put more thought into their work than almost anyone I’ve met in business."

“Kraig and the Bearhug team are one of the best startup recruiting firms I have ever met.”

"Kraig, we are thrilled to formally finish the process. Congratulations on your helping us get an amazing new executive to our company!"

"Having seen Bearhug from both sides, as a candidate & client, their approach is unmatched. Radical transparency and hands-on coaching delivered results that felt like a miracle."

“Bearhug’s outreach stood out immediately — specific, contextual, and focused on real impact. The process was collaborative, transparent, and the most thoughtful I’ve ever experienced."

“Bearhug’s approach was refreshing — transparent, knowledgeable, and focused on adding value from the start. Their approach turned a high-stakes role into a smooth, confidence-building experience.”

"Bearhug is the recruiting partner high-growth businesses need — experienced, transparent, and realistic about what’s possible in senior searches. They bring urgency and deep preparation to every step."

"Bearhug does things differently. The process was thoughtful, transparent, and executed with a level of rigor and insight I didn’t expect."

"I was initially skeptical, but Bearhug quickly proved different — down-to-earth, empathetic, and thorough. They exceeded all expectations and delivered a great outcome for both sides.”

"Bearhug’s process was extremely structured, efficient, and effective. Unlike anything I’d ever experienced. The level of detail and organization gave me total confidence at every step."

"Getting to know the Bearhug team through such a thoughtful, structured process was a standout experience. Any high-growth startup needing specific executive hires should expect not just results, but a process that makes candidates want to join."

🔥Hot Off the Press

Free Report: The 27 Most Painful & Expensive Mistakes Tech Startup CEOs Make Before Launching an Executive Search (and How to Avoid Them!)