StrictlyVC Download Rethinking series A in the age of mega funds
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Feb 17, 2026 
Stacy Brown-Philpot, founder and managing partner of Cherry Rock Capital and former TaskRabbit CEO with Google experience. She explains why she launched a firm to fill a Series A/B gap. She talks about evaluating product-market fit at scale. She discusses AI’s impact on enterprise software. She stresses quality revenue over headline ARR and how board roles shape investment judgment.
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Filling The Series A/B Gap
- Stacy Brown-Philpot launched Cherry Rock to fill a Series A/B gap for underinvested founders after seeing a lack of later-stage operating-focused funds.
- The firm targets U.S.-based software companies led by underinvested entrepreneurs and concentrates on 12–15 portfolio companies.
Pipeline Is Robust, Not Scarce
- Cherry Rock found no pipeline problem, entering 2025 with over 2,000 companies in its pipeline and adding 950 more that year.
- The firm had invested in almost five companies and is actively targeting a concentrated portfolio to add value.
Coactive AI Investment Story
- Cherry Rock backed Coactive AI, an infrastructure-layer multimodal AI firm serving media and entertainment, and led its Series B with Emerson Collective.
- Stacy first invested personally before the Series A and watched the company scale into a market under heavy scrutiny.