Drew Madison
2× Founding Seller | Winning Enterprise Customers Before There’s a Playbook
ex-AdRollI'm a 2× Founding Seller (one exit, one pre-seed to Series C) who builds repeatable enterprise revenue before there's a playbook. I closed the first 150 customers at Automox, building the GTM engine from zero.
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Before that, I built and led AdRoll's NYC Mid-Market business as the company scaled from $10M to $200M+ in After founding, selling and leading teams, I keep coming back to the early stage, where every customer has to be Outside of work, you'll usually find me in the mountains around Boulder, preparing for an endurance event that sounded like a good idea at the time. Right now, I'm training for the Grand Traverse ultra from Crested Butte to Aspen in September.
GTM Index
- DMM DIGITAL VENTURESJOB
- Founder | GTM Operator3Y 6M
Founder | GTM Operator
DMM Digital Ventures
Partner with early-stage SaaS founders on ICP, outbound and early sales execution through advisory and embedded operator engagements. • Advise pre-seed and Series A SaaS founders on enterprise GTM strategy, ICP, outbound pipeline generation and early sales execution using the same zero-to-one motion I've built twice as a Founding Account Executive • Build repeatable outbound and enterprise sales motions for early-stage SaaS companies selling complex technical products to engineering, IT and security teams • Built profitable AI-assisted digital media businesses and content operations
- ADROLLJOB
- Sr. Mgr of New Business Sa…2Y 3M
Sr. Manager of New Business Sales (Promoted from Manager, Strategic AE)
AdRoll
• 2022 President’s Club, ranking #1 globally in New Business Leadership (127% attainment) • Exceeded quota as a Strategic AE (126% attainment), consistently ranking top 10% in weekly pipeline generation • Recruited back based on prior success as a top IC and leader during hypergrowth ($10M → $200M+)
- Head of Sales, NYC Mid-Mar…3Y 11M
Head of Sales, NYC Mid-Market (promoted from Team Lead and Account Executive)
AdRoll
2013: Inc 5000 #12 Fastest-Growing Private Company in the U.S. • Selected as foundational hire to launch NYC office; built NYC Mid-Market division to $20M+ • As AE: 156% in 2012; 113% in 2013; never missed a quarter • As leader: Ranked #1 of 7 (2014) and #2 of 12 (2015)
- AUTOMOXJOB
- Dir of Enterprise Sales (F…4Y 5M
Director of Enterprise Sales (Founding AE/VP of Sales)
Automox
• Founding sales hire and early executive team member, responsible for all company revenue generation as the initial VP of Sales and founding seller, building outbound motion, ICP, pricing and sales playbook from zero in a pre-seed environment • Closed first 150 customers by building pipeline through outbound prospecting and converting technical champions into enterprise deals without SDR support • Exceeded quota from 2017-2019 and closed $250K-$750K enterprise deals with CISO and CTO stakeholders at NTT, Thermo Fisher Scientific, Xerox, Canada Goose, Yale University and others • Following Series B, transitioned from founding VP of Sales to Director of Enterprise Sales, continuing to lead…
- TECHTARGETJOB
- Sales (Exit - Acquired by…6Y 5M
Sales (Exit - Acquired by TechTarget)
TechTarget
TechTarget acquired BeyeNETWORK in April 2010. • Founding sales hire at BeyeNETWORK; scaled revenue through acquisition by TechTarget and transitioned to strategic accounts team • Closed Fortune 500 logos including Microsoft, Oracle, IBM, CA and SAP
- Job: DMM Digital Ventures — Founder | GTM Operator · 2023-04 – present · 3y 4mo — Partner with early-stage SaaS founders on ICP, outbound and early sales execution through advisory and embedded operator engagements. • Advise pre-seed and Series A SaaS founders on enterprise GTM strategy, ICP, outbound pipeline generation and early sales execution using the same zero-to-one motion I've built twice as a Founding Account Executive • Build repeatable outbound and enterprise sales motions for early-stage SaaS companies selling complex technical products to engineering, IT and security teams • Built profitable AI-assisted digital media businesses and content operations
- Job: AdRoll — Sr. Manager of New Business Sales (Promoted from Manager, Strategic AE) · 2021-04 – 2023-07 · 2y 3mo — • 2022 President’s Club, ranking #1 globally in New Business Leadership (127% attainment) • Exceeded quota as a Strategic AE (126% attainment), consistently ranking top 10% in weekly pipeline generation • Recruited back based on prior success as a top IC and leader during hypergrowth ($10M → $200M+)
- Job: Automox — Director of Enterprise Sales (Founding AE/VP of Sales) · 2016-11 – 2021-04 · 4y 5mo — • Founding sales hire and early executive team member, responsible for all company revenue generation as the initial VP of Sales and founding seller, building outbound motion, ICP, pricing and sales playbook from zero in a pre-seed environment • Closed first 150 customers by building pipeline through outbound prospecting and converting technical champions into enterprise deals without SDR support • Exceeded quota from 2017-2019 and closed $250K-$750K enterprise deals with CISO and CTO stakeholders at NTT, Thermo Fisher Scientific, Xerox, Canada Goose, Yale University and others • Following Series B, transitioned from founding VP of Sales to Director of Enterprise Sales, continuing to lead…
- Job: AdRoll — Head of Sales, NYC Mid-Market (promoted from Team Lead and Account Executive) · 2012-05 – 2016-04 · 3y 11mo — 2013: Inc 5000 #12 Fastest-Growing Private Company in the U.S. • Selected as foundational hire to launch NYC office; built NYC Mid-Market division to $20M+ • As AE: 156% in 2012; 113% in 2013; never missed a quarter • As leader: Ranked #1 of 7 (2014) and #2 of 12 (2015)
- Job: TechTarget — Sales (Exit - Acquired by TechTarget) · 2005-11 – 2012-04 · 6y 5mo — TechTarget acquired BeyeNETWORK in April 2010. • Founding sales hire at BeyeNETWORK; scaled revenue through acquisition by TechTarget and transitioned to strategic accounts team • Closed Fortune 500 logos including Microsoft, Oracle, IBM, CA and SAP
Skills
Playbooks
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