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Salary: USD 350,000 - 350,000 / annual
Tailscale is a secure networking platform built on WireGuard that helps organizations securely interconnect people and devices. The company is fully distributed, founded in 2019, and backed by top-tier VCs including Accel, CRV, and Insight.
As a founding Strategic Account Executive, you will own a focused portfolio of large enterprises 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 with CIOs, CISOs, CTOs, and senior technical and business leaders.
Key responsibilities include:
- Developing account strategies that connect customer priorities with opportunities across business units, geographies, and use cases
- Driving personalized outbound prospecting and account-based campaigns in partnership with SDRs and Marketing
- Managing complex deals through long sales cycles, competitive pursuits, and intricate buying processes
- Building and maintaining executive relationships while developing internal champions
- Collaborating with Customer Engineering, GTM Engineering, Customer Success, Product, Engineering, executive leadership, Legal, and Finance to win and expand strategic accounts
- Testing new approaches and shaping the enterprise sales playbook based on what works
- Maintaining disciplined CRM hygiene, accurate forecasts, and actionable account plans
You'll help define how Tailscale wins in the enterprise market, working closely with the Director of Strategic Sales and executive leadership in a small, highly collaborative team.
REQUIREMENTS:
- 5+ years of success as a top-performing enterprise or strategic seller in early-stage, high-growth environments
- Proven success selling to organizations with 10,000+ employees and closing complex six and seven-figure SaaS deals
- Consistent track record of achieving or exceeding annual performance targets with demonstrated year-over-year growth and sustained results
- Ability to earn executive trust, engage technical stakeholders, and navigate procurement, legal, and financial reviews
- Strong business judgment, clear written and verbal communication, and collaborative, accountable approach
- Comfort with ambiguity and enthusiasm for building a sales motion while carrying a quota
- Demonstrated commitment to CRM hygiene, accurate opportunity management, pipeline tracking, and forecast reliability
- Proven ability to lead value-based sales conversations and quantify business impact to build compelling ROI-driven business cases
PREFERRED EXPERIENCE:
- Experience as an early sales hire or helping build a new enterprise sales motion
- Strong technical acumen; background in selling infrastructure, networking, cybersecurity, developer tools, or cloud software is a bonus
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
