Head of Sales & Revenue Expansion

10+ years of progressive sales leadership experience Proven success scaling ARR in subscription or tech-enabled services businesses Experience selling to SMB and commercial customers and/or through professional partners Deep understanding of subscription economics (ARR, LTV, CAC, payback, retention) Strong operational discipline across pipeline management and forecasting Experience partnering closely with Product, Growth, and Operations Hands-on experience with modern sales tooling and AI-enabled platforms Comfort operating in ambiguity and building from first principles Data-driven judgment with decisions anchored in metrics

Own end-to-end sales strategy, execution, and performance Drive ARR growth across Micro-SMB, commercial, and professional/partner channels Build and scale the Revenue System and sales operating cadence Lead and scale the sales team, setting goals and fostering a culture of ownership Execute pipeline generation, conversion rates, and deal velocity Increase ARR per customer through expansion, cross-sell, upsell, and retention Deploy AI tools to improve sales processes and forecast accuracy