Jason Finkelstein
Jason Finkelstein
About
Detail
Fractional CMO
California, United States
I'm a track record GTM operator and leader (COO, CMO, CRO, President). I build 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 $20K 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 (COO, CMO, CRO, President) as well as coaching/advising CEOs as I look for my next full-time role leading GTM, Ops and/or Marketing at high-growth later-stage software companies.
Recent fractional engagements include Fello.ai, MirrorWeb, Higharc, Shelf.io and Numa, where I’ve worked hands-on with founders and leadership teams across positioning, category strategy, demand generation, sales velocity and GTM operations.
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, including helping shape Numa’s early go-to-market foundation.
Where I Thrive
→ Translating company vision into customer-facing category leadership and brand
→ Creating sales velocity machines with more pipeline, larger deals and higher win rates
→ Helping CEOs and executive 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, Numa, Wyllo/NoFraud, Swellbox (acq. by Datavant), Alyce (acq. by Sendoso), Linqia and Disconnect.
I’m currently doing fractional work as an embedded GTM executive (COO, CMO, CRO, President) as well as coaching/advising CEOs as I look for my next full-time role leading GTM, Ops and/or Marketing at high-growth later-stage software companies.
Recent fractional engagements include Fello.ai, MirrorWeb, Higharc, Shelf.io and Numa, where I’ve worked hands-on with founders and leadership teams across positioning, category strategy, demand generation, sales velocity and GTM operations.
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, including helping shape Numa’s early go-to-market foundation.
Where I Thrive
→ Translating company vision into customer-facing category leadership and brand
→ Creating sales velocity machines with more pipeline, larger deals and higher win rates
→ Helping CEOs and executive 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, Numa, Wyllo/NoFraud, Swellbox (acq. by Datavant), Alyce (acq. by Sendoso), Linqia and Disconnect.
