About
Senior thinking. Direct involvement.
Headwall Ventures is a principal-led advisory practice focused on commercial strategy, growth, and execution. Its approach is shaped by work with businesses from early-stage startups to publicly traded companies—sometimes advising founders directly, sometimes working alongside marketing leadership, and often doing the implementation work itself.
How we operate
- 01
Diagnose the actual problem.
- 02
Make decisions based on economics and organizational realities.
- 03
Stay close enough to implementation to see what works.
Founder / Principal
Alex Mathews
Founder & Principal, Headwall Ventures
Alex has spent nearly two decades in performance marketing and early-stage technology. He founded Headwall in 2018 as a collective of performance marketers from agencies and in-house teams, growing it into a seven-figure growth marketing practice with $25M in ad spend under management within its first 18 months.
Alongside Headwall, he has advised venture capital, private equity, and hedge fund clients on the social advertising landscape, marketing and ad technology, and omni-channel commerce — including commercial due diligence on portfolio and prospect companies. He is also an active angel investor in early-stage companies, both directly and through SPVs.
Previously, Alex served as SVP of Media at Overdrive, led paid social strategy at Elite SEM, and spent several years at Nanigans, where he oversaw $50M+ in ad spend and helped build the accounts team from its second hire. He began his career in equities trading and co-founded a MassChallenge-incubated mobile startup. He is based in the Greater Boston area.