Head Of Sales, North America

Nearly every company in the world runs on custom software for critical operations like tracking performance metrics, handling customer support workflows, building admin dashboards, and countless other processes. At Retool, we’re building the first enterprise AppGen platform: software that transforms natural language into production-ready code, integrates directly with business data, and meets the highest standards of security and governance. Over 100 million hours of work has been automated by developers and domain experts using our platform, freeing them to focus on creative problem-solving and strategic initiatives that drive real business value.

About the role

Retool is redefining how enterprises build software—AI-powered, developer-first, and enterprise-grade. As we expand more deeply into complex, global organisations, we’re seeking an accomplished sales leader to scale and elevate our business across North America. This is a hands-on leadership role where you’ll be building and coaching a team of Account Executives responsible for closing multi-threaded, six- and seven-figure deals. You’ll work directly with some of the most forward-thinking technical teams in the world, helping them adopt Retool as their application layer for AI. It’s a rare opportunity to join a high-growth company at a pivotal stage. You’ll shape our enterprise motion, refine how we sell, and develop the next generation of top-performing sellers.

Responsibilities

• Own the North America revenue number and build the strategy to consistently exceed it quarter after quarter
• Define and evolve our segmentation strategy, coverage model, and GTM motion based on rigorous analysis of what's actually working
• Partner closely with Marketing, TCX, and Product to create a seamless customer experience
• Recruit, develop, and retain exceptional sales talent who thrive in our high-performance, high-curiosity culture
• Design compensation plans, career paths, and enablement programs that attract A-players and help them do the best work of their career
• Create a coaching culture where managers develop their people as consistently as they manage their numbers
• Build scalable sales motions that maintain our high-touch customer experience as we grow
• Get your hands dirty: model the behaviors you want to see, whether that's running a critical deal, shadowing a struggling rep, or rebuilding a territory plan

Requirements

• 15+ years in B2B software sales with 8+ years leading sales teams at scale
• Proven experience building and scaling sales organizations through significant growth phases
• Track record of consistently hitting or exceeding revenue targets in competitive markets
• Experience selling technical products to technical buyers, ideally developer tools, infrastructure, or platform software
• Strategic thinker who can zoom out to see market trends and zoom in to diagnose a stuck deal
• Natural coach who develops people by making them better thinkers, not just better executors
• Exceptional communicator who can translate complex ideas simply and rally teams around a clear vision
• Comfortable with ambiguity; you build the bridge while walking across it

Benefits

• Comprehensive benefit plan, including medical, dental, vision, and 401(k)
• Generous hybrid work policy

Pay

For candidates based in San Francisco, the pay range for this role is $500,000—$650,000 USD (on-target earnings for commissionable roles). For candidates based in New York, the pay range is $500,000—$650,000 USD. Additional compensation in the form of equity and/or commission/bonuses may apply. Pay and benefits are subject to change at any time.