Regional Sales Director
Lead a team of Account Executives to drive net-new and expansion revenue from Fortune 500 accounts for AI software agents and developer tools. Player-coach role owning quota, closing large deals, hiring/coaching AEs, and shaping GTM strategy in a fast-paced AI startup.
About the job
What You'll Own
Revenue Execution
- Own quarterly and annual bookings quota for your territory across new logo acquisition and expansion
- Manage a pipeline of $5M--$20M+ ARR opportunities with average deal sizes of $1M+
- Forecast accurately using MEDDIC; maintain deal hygiene and stage discipline
- Be in the rooms that matter -- EBCs, executive dinners, key negotiations -- alongside your AEs
Team Leadership
- Recruit, hire, and develop a team of 3-6 Enterprise AEs
- Run rigorous weekly 1:1s and deal reviews focused on qualification, strategy, and close plans
- Build a team culture of accountability, intellectual curiosity, and competitive drive
- Identify performance gaps early and coach or make personnel changes decisively
Territory and GTM Strategy
- Define territory segmentation and account prioritization within your vertical
- Build vertical-specific messaging and competitive positioning in partnership with Marketing and Product
- Partner with post-sales to expand the installed base and protect renewals
- Develop executive relationships within key accounts that extend beyond the AE layer
Cross-functional Influence
- Serve as the voice of the field - surface product gaps, competitive intelligence, and customer insights to leadership
- Collaborate with Deployed Engineering to scope and deliver compelling POCs and technical evaluations
- Work with Legal and Finance on complex contract structures, MSAs, and non-standard terms
What We're Looking For
Required
- 7+ years of enterprise software sales experience, including at least 2 years managing a team of high-level AEs
- 2+ years of experience successfully selling into F500 companies
- Demonstrated track record closing $1M+ ARR deals with F500 accounts in a complex, multi-stakeholder sales motion
- Experience selling to CIO, CTO, SVP/VP Engineering, or equivalent technical executive buyers
- Proficiency in MEDDIC or a comparable enterprise sales methodology
- History of overachievement against quota as both an IC and a manager
- Ability to recruit and close top-tier sales talent in a competitive market
Strongly Preferred
- Vertical-relevant domain expertise - working knowledge of buyer personas, budget cycles, and procurement dynamics in the vertical
- Prior 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, including GitHub Copilot, Cursor, Windsurf, and emerging agentic tools
Skills
Enterprise Software Sales, MEDDIC, Account Management, Sales Forecasting, Team Management, Poc Scoping, Contract Negotiation, Competitive Analysis
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