Bearhug Recruiting Places Chief Product Officer at ServiceUp — A Case Study in Executive Search, Founder–Board Alignment, and Scaling Product Leadership in a Fragmented $200B+ Market.
At Bearhug Recruiting, our mission is to help founders and boards secure leaders who can change the trajectory of their companies. We’re excited to share one of our latest success stories: placing Amit Shrivastava as Chief Product Officer at ServiceUp.
The Challenge
ServiceUp is an AI-powered platform modernizing vehicle repair for fleets and insurance carriers. Backed by $55M in Series B funding from PeakSpan Capital, it has quickly become one of the fastest-growing U.S. startups.
As the company was finalizing its Series B and preparing for its first post-round board meeting, the leadership team faced a critical challenge: ~75% of the next growth phase depended on strong product leadership. Waiting to hire wasn’t an option.
The team had scaled to ~60 full-time employees plus 15–20 contractors distributed across Mexico, India, the Philippines, and Kenya. In a fragmented, operationally heavy $200B+ market, ServiceUp needed a CPO who could bring clarity, vision, and execution fast.
CEO Brett Carlson and the board, led by Jack Freeman of PeakSpan Capital, were aligned: this hire would be a head-turner — someone who could expand TAM, own the transaction flow (“DoorDash for car repair”), and elevate the product function ahead of adding a future CTO.
The Search
Bearhug Recruiting was brought in during late-stage diligence on the Series B. Our mandate: deliver a world-class product leader in less than 90 days.
We knew the right candidate might not come from autotech itself — depth was limited there. Instead, we looked to adjacent industries where AI-native tools had already scaled. Healthcare emerged as a strong parallel: complex ecosystems, fragmented stakeholders, and outcomes-driven products.
The Match
That path led us to Amit Shrivastava, who wasn’t actively looking but was open to opportunities where his experience could create outsized impact.
Founding Product Manager at Twin Health: Amit built the MVP, grew the product, design, analytics, and content teams from scratch, and helped scale the company to unicorn valuation.
AI for Real Outcomes: Twin’s platform reduced or eliminated medication use for ~80% of users, demonstrating Amit’s ability to connect product innovation to measurable results.
Global Scale: He launched health tech in India before expanding to the U.S., proving his ability to operate in complex, underserved markets.
Prior Experience: Roles at Castlight Health, McAfee, and Intel sharpened his expertise in launching and scaling B2B and marketplace platforms.
Amit’s background aligned directly with ServiceUp’s north star: building lightweight software for shops, insurers, and fleets while driving TAM expansion and transaction ownership.
The Outcome
ServiceUp secured its new CPO.
From our client: “We got the perfect person for this moment. I’m 100% convinced we have the right guy for what the market offers and what we need.” — Brett Carlson, CEO @ ServiceUp
From the Candidate: “I joined ServiceUp as CPO. The match was strong both ways — my experience scaling marketplaces and building product teams mapped directly to their mission of becoming the ‘DoorDash for car repair.’” — Amit Shrivastava, CPO @ ServiceUp
For Bearhug, this project showcased the power of founder–board alignment, precision sourcing, and a process built on depth and transparency. By looking beyond the obvious lane, we found a leader who brings both executive presence and builder-level drive.
Looking Ahead
With Amit now in place as CPO, ServiceUp is positioned to:
Scale its AI-powered ecosystem.
Expand product capabilities across fleets, insurers, and shops.
Own the repair — and ultimately own the transaction flow in a $200B+ industry.
This placement marks a pivotal moment not just for ServiceUp, but for the broader auto repair ecosystem. And for Bearhug, it’s another example of our philosophy in action: we fish and we dish — delivering leaders who transform companies.
