VP Sales Search
Bites (PeakSpan Portfolio)
The Mandate
Bites is a mobile-first, AI-powered microlearning and communication platform for frontline and deskless workforces, backed by growth investor PeakSpan Capital and scaling beyond its seed-stage roots toward the $5M to $50M ARR range PeakSpan targets. The company needs a VP of Sales to build and lead a repeatable, scalable go-to-market engine across enterprise and mid-market accounts in retail, consumer goods, manufacturing, and healthcare verticals. This leader will own new-business pipeline, quota-carrying team hiring and coaching, and sales process rigor to accelerate ARR growth as the company expands its U.S. commercial footprint.
Competencies That Matter
B2B SaaS new-business revenue ownership, Sales team building and coaching, Enterprise and mid-market pipeline generation, Repeatable sales process and playbook design, Forecasting and CRM-driven pipeline discipline, Board and investor-level reporting, Land-and-expand and account growth motion
Experience Profile
The ideal candidate has led sales at a growth-stage B2B SaaS company, ideally in HR tech, learning and development, sales enablement, or frontline workforce software, and has personally scaled ARR through and beyond the early growth stage. They bring a track record of building quota-carrying teams from a small base, selling into retail, consumer goods, manufacturing, and healthcare buyers, and operating within a private-equity or venture-backed environment with strong metrics accountability.
Cultural Indicators
Bites is a founder-led, product-driven company with an entrepreneurial, fast-moving culture and roots in an Israeli engineering team now expanding its U.S. commercial presence. The right leader is a hands-on, roll-up-the-sleeves builder comfortable with ambiguity, cross-cultural collaboration, and setting go-to-market foundations rather than inheriting a mature machine.
Target Geography
National, US
Target Compensation Band
$200K-$260K base + equity, $400K-$500K OTE
Target Start Date
ASAP
Talent by Metro
Titles: VP Sales, SVP Sales, Chief Revenue Officer, Head of Sales, VP Revenue, VP Commercial, VP Enterprise Sales, VP Go-to-Market, Country Manager, General Manager | Industries: Software, SaaS, Enterprise Software, Cloud Software | Level: C-Suite, VP | Each dot represents one titled sales leader at a company of 11 to 1,000 employees | August 2026
Alon
JUNIORThe Pattern
Came up through inside sales and account management at earlier stage software and consumer technology companies, shaped by a hands on quota carrying environment where the team was small and process was still being built, now at a junior tier that has not yet owned a full sales organization at the VP level.
✓What This Type Brings
- •A candidate like this has typically operated inside the exact early growth window this company is in, close enough to the deals to still sell personally while beginning to build repeatable process for a small team.
- •This profile buys a lower cost seat with high hunger and something to prove, credible with individual contributors because the gap to their daily work is small and the memory of carrying a bag is recent.
- •A candidate like this has typically carried the pipeline discipline and hands on deal mechanics that a more senior hire would have delegated away, which matters when the founder still needs someone in the trenches.
⚠What You're Betting On
- •You are betting that strong individual and small team selling in one environment transfers into leading, hiring and structuring a full sales function in a different vertical and motion.
- •You are betting that the discount you get at this tier is not erased by a longer ramp, because if quota and hiring targets slip the org loses a full growth cycle before you can correct.
- •You are betting that a junior leader can hold their own with an involved founder and any existing senior commercial voices, setting direction rather than simply executing what the room already decided.
Alaina
MID-LEVELThe Pattern
Came up through sales execution and quota-carrying leadership at high growth software companies, seasoned in a venture-backed environment where building repeatable pipeline mattered more than managing a mature book, now at a mid-level tier having built and scaled a sales function once and looking to translate that playbook from one context to another.
✓What This Type Brings
- •A candidate like this has typically operated inside an early to growth stage software company where the sales motion was still being defined, which maps directly to a company still assembling its go-to-market engine and needing a leader who can build rather than inherit.
- •This profile at the mid-level tier buys meaningful hunger and upside at a more accessible compensation point, credible enough to earn respect from an existing sales team without commanding the premium or entrenched expectations of a fully seasoned executive.
- •A candidate like this has typically carried a network of individual contributors and sales managers from prior growth environments, along with the process discipline around pipeline hygiene, forecasting, and quota design that a more junior hire would not yet own.
⚠What You're Betting On
- •You are betting that a playbook built in one funding stage and vertical transfers cleanly into a smaller, less structured environment where the leader must operate without the scaffolding a larger organization provided.
- •You are betting that results materialize on a timeline that justifies the mid-level investment, because a slow ramp at this tier still costs real quarters of pipeline and a rebuild if the fit is wrong.
- •You are betting that this tier navigates heavy founder involvement and an existing internal power structure with enough diplomacy to drive change without triggering the politics that stall a first-time senior builder.
Doug
SENIORThe Pattern
Came up through enterprise sales and revenue leadership at high growth software and consumer platforms, sharpened by scaling repeatable go to market motions across multiple growth stages, now operating at the senior tier with a track record of building and leading VP level sales organizations multiple times at significant scale.
✓What This Type Brings
- •A candidate like this has typically built and scaled sales teams through the exact inflection point this company faces, matching a growth stage that needs repeatable pipeline generation and a first true revenue operating layer.
- •This profile buys immediate credibility with founders and early sellers, and while it commands a premium compensation package, the tradeoff is a leader who can architect the org rather than one who needs to be taught how.
- •A candidate like this carries a ready network of proven sales hires, established playbooks for quota setting and territory design, and the process discipline to install forecasting and pipeline rigor from day one.
⚠What You're Betting On
- •You are betting that a leader accustomed to larger, better resourced organizations can operate effectively at this company's smaller scale and stay energized by hands on building rather than pure management.
- •You are betting that the premium cost of a senior hire produces measurable pipeline and bookings movement fast enough to justify the burn, because a slow ramp at this tier is expensive to carry and hard to unwind.
- •You are betting that a seasoned operator will integrate smoothly with a hands on founder and existing power structures, ceding autonomy where needed without triggering friction over ownership of the revenue function.
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Prepared for Bites by Bearhug Recruiting | Confidential