Strategic Enterprise Account Executive

Tailscale makes it simple for organizations to securely connect people, devices, and workloads anywhere in the world. As adoption grows within the world’s largest enterprises, we’re launching a Strategic Sales team to support our next stage of growth.

As a founding Strategic Account Executive, you’ll own a focused portfolio of organizations with 10,000+ employees, including Fortune 1000 and Global 2000 companies. You’ll lead complex opportunities from initial engagement through close and expansion, building executive relationships and connecting customer priorities with Tailscale’s capabilities.

You’ll help define how we win in this market - developing outbound strategies, testing new approaches, and creating a playbook for future growth. Reporting to the Director of Strategic Sales, you’ll join a small, highly collaborative team and partner closely with executive leadership and teams across the business.

Key Responsibilities

• Own account strategy: Build account plans that connect customer priorities with opportunities across business units, geographies, and use cases
• Create pipeline: Drive personalized outbound prospecting, partnering with SDRs and Marketing on coordinated account-based campaigns
• Lead complex deals: Manage opportunities through negotiation and close, navigating long sales cycles, competitive pursuits, and complex buying processes
• Build executive relationships: Earn trust with CIOs, CISOs, CTOs, and senior technical and business leaders while developing champions across the organization
• Bring the right team together: Partner with Customer Engineering, GTM Engineering, Customer Success, Product, Engineering, executive leadership, Legal, and Finance to win and grow strategic accounts
• Shape the playbook: Test approaches, share what works, and bring customer feedback to teams shaping Tailscale’s product and enterprise strategy
• Execute with discipline: Maintain clear qualification, accurate forecasts, and actionable account and opportunity plans

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