Jason Finkelstein
California
Overview
I'm a track record GTM leader and operator (CMO, CRO, President) who builds AI-native GTM teams that drive profitable growth. My career spans category-defining SaaS and vertical AI companies from $10M to $400M+ ARR, with ACVs ranging from $25K to $2M. Along the way, I've led big teams and small with product-led, sales-led, community-led and hybrid GTM motions. I've shaped category strategy with strategic narratives, and delivered 5 exits ranging from $25M to $1.4B. I’m currently doing fractional work as an embedded GTM executive (CMO, CRO, President) as well as coaching/advising CEOs as I loo
About
I'm a track record GTM leader and operator (CMO, CRO, President) who builds AI-native GTM teams that drive profitable growth. My career spans category-defining SaaS and vertical AI companies from $10M to $400M+ ARR, with ACVs ranging from $25K to $2M. Along the way, I've led big teams and small with product-led, sales-led, community-led and hybrid GTM motions. I've shaped category strategy with strategic narratives, and delivered 5 exits ranging from $25M to $1.4B. I’m currently doing fractional work as an embedded GTM executive (CMO, CRO, President) as well as coaching/advising CEOs as I look for my next full-time role leading GTM and Marketing at later-stage software companies. Recently I was CMO of Numa, AI agents for automotive dealerships. I previously led marketing at Gladly (AI-first CX platform), AdRoll (display retargeting pioneer for ecommerce), sales and marketing at Traitify (acquired by Paradox AI, acquired by Workday for $1B), AVG security (publicly-traded, acquired by Avast for $1.4B) and Location Labs (acquired by AVG for $220M). I’ve also served as CRO, President, and CEO Advisor across numerous B2B software businesses and was an original co-founder of Numa. Where I Thrive → Translating company vision into customer-facing category leadership and brand → Creating sales velocity machines, more pipeline with larger $ deals and higher win rates- Helping CEOs and exec teams prioritize and execute the highest impact work → Applying AI to unlock efficiency and scale for GTM workflows → Leading, coaching, mentoring high-performing teams from 5 to 100+ incl full-stack Marketing, Sales, Sales Development, Customer Success and Support Notable Exits → Location Labs → AVG ($220M) → AVG → Avast ($1.4B) → Traitify → Paradox.ai → Workday ($1B) → Swellbox → Datavant → Alyce → Sendoso Advisory Work I advise growth-stage CEOs on GTM, strategy, positioning, category design, demand gen and growth. Recent: Fello, MirrorWeb, NoFraud, Swellbox (acq. by Datavant), Alyce (acq. by Sendoso), Linqia, Disconnect and Numa.