Gregory Whelan

Background

About Gregory Whelan

Enterprise SaaS sales leader with a proven track record of building and scaling revenue in high-growth startups. At DocNow, I owned company revenue growth from $100K → $3M+ ARR in under three years, consistently surpassing company-wide revenue targets at levels equivalent to 120–200% quota attainment in comparable SaaS sales roles. I thrive in complex B2B sales environments — negotiating six- and seven-figure contracts, aligning with customer success and product teams to drive adoption, and navigating compliance with IT and security leaders (PHI, HIPAA). Known for my ability to build sales engines from scratch, I’ve designed GTM playbooks, CRM and pipeline infrastructure, and customer enablement systems that accelerate both adoption and expansion. My career spans fintech, healthtech, and SaaS startups — always at the intersection of growth, technology, and complex enterprise needs. Core strengths: consultative sales, GTM design, sales accountability, C-suite negotiation, CS alignment, enterprise compliance, ARR scaling, CRM/HubSpot strategy.