I help SaaS founders and operators build repeatable outbound systems, sharpen GTM execution and navigate complex enterprise sales without wasting months figuring it out alone.
2× founding seller • Closed first 150 customers at Automox • Built $20M division at AdRoll
Let's talk →Build outbound systems that consistently generate qualified pipeline.
Create structure, visibility and momentum across your sales process.
Navigate complex enterprise deals from discovery through close.
Use AI to accelerate testing, messaging refinement and market validation.
I'm Drew Madison, founder of DMM Digital Ventures. I've spent my career building pipeline from zero, closing complex enterprise deals and helping scale high-growth SaaS companies from early traction to repeatable GTM execution.
Today I work with founders and operators who need more than generic sales advice. I bring hands-on experience building outbound motions, navigating enterprise buying committees and turning early momentum into scalable revenue systems.
No pitch decks required. Just a straight conversation about where you are, where you want to go and whether I can help.
Email Drew →