Regional Sales Director

TL;DR

Regional Sales Director (Enterprise Sales): Lead a team of Account Executives driving net-new and expansion revenue across Fortune 500 accounts with an accent on player-coach deal execution, MEDDIC forecasting, and building a high-ownership enterprise sales motion. Focus on recruiting and developing AEs, owning $5M--$20M+ ARR pipeline, and partnering across engineering, post-sales, legal, and finance to win complex multi-stakeholder deals.

Location: San Francisco, Austin, New York City (On-site)

Company

Windsurf builds Devin, an AI software engineer, and Windsurf, an AI-native IDE for collaborative AI teammates.

What you will do

• Own quarterly and annual bookings quota across new logo acquisition and expansion within the assigned territory.
• Manage a pipeline of $5M--$20M+ ARR opportunities with average deal sizes of $1M+.
• Forecast accurately using MEDDIC and maintain deal hygiene and stage discipline.
• Recruit, hire, and develop a team of 3–6 Enterprise Account Executives; run weekly 1:1s and deal reviews.
• Lead strategy and close alongside AEs on the largest deals, including key negotiations and executive business reviews.
• Partner with post-sales to expand the installed base and protect renewals; collaborate with Deployed Engineering on POCs and technical evaluations; work with Legal and Finance on complex contract structures.

Requirements

• 7+ years of enterprise software sales experience, including 2+ years managing a team of high-level AEs.
• 2+ years of experience selling into Fortune 500 companies.
• Proven track record closing $1M+ ARR deals with Fortune 500 accounts in complex, multi-stakeholder sales motions.
• Experience selling to CIO, CTO, SVP/VP Engineering, or equivalent technical executive buyers.
• Proficiency in MEDDIC (or a comparable enterprise sales methodology).
• Vertical-relevant domain expertise and familiarity with buyer personas, budget cycles, and procurement dynamics.

Nice to have

• Experience selling developer tools, AI/ML platforms, cloud infrastructure, or adjacent technical products.
• Track record at a high-growth startup or scale-up (Series B through IPO stage).
• Familiarity with the competitive landscape in AI coding (e.g., GitHub Copilot, Cursor, Windsurf, agentic tools).

Culture & Benefits

• High-ownership, fast-moving environment with expectations to adapt strategy as learning happens.
• Player-coach role focused on being in the field and knowing every major deal.
• Established, fully staffed team; you will hire some of your AEs.
• Enterprise sales motion with strong cross-functional collaboration across engineering, post-sales, legal, and finance.