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Salary: USD 250,000 - 300,000 / annual
Tailscale is a rapidly growing, fully distributed secure networking platform built on WireGuard, backed by top-tier VCs (Accel, CRV, Insight, Heavybit, Uncork Capital). The company helps organizations of all sizes securely interconnect people and devices, simplify network access, and strengthen security posture.
As an Enterprise Account Executive, you will own and grow a territory of enterprise organizations, driving both net-new customer acquisition and expansion revenue. You will be responsible for the full sales cycle—from prospecting through close—working with sophisticated technology organizations to help them modernize legacy networking and security infrastructure.
Key responsibilities include:
- Self-sourcing pipeline through outbound prospecting, cold outreach, and strategic account targeting
- Developing strategic account plans identifying key stakeholders, organizational priorities, and expansion paths
- Building relationships with Security, Infrastructure, Engineering, Compliance, and Executive stakeholders
- Navigating complex enterprise sales cycles with multiple decision-makers, procurement, security reviews, and legal negotiations
- Positioning Tailscale as a strategic platform by translating technical capabilities into measurable business outcomes
- Leading cross-functional account teams (Sales Engineering, Customer Success, Product, Marketing, Support)
- Driving adoption beyond initial deployment to identify broader organizational usage and long-term growth
You will partner closely with Solutions Engineering and collaborate across Customer Success, Support, Marketing, and Product teams. Success is measured by consistently exceeding quota through a mix of self-generated pipeline, new customer acquisition, and account expansion; establishing trusted advisor relationships with technical and business leaders; and building predictable pipeline through disciplined prospecting.
REQUIREMENTS:
- 5+ years of closing experience in a sales role
- Demonstrated success selling infrastructure, networking, cybersecurity, cloud, developer tools, or other highly technical software solutions
- Proven track record of consistently meeting or exceeding quota in an enterprise sales environment
- Experience managing complex, multi-stakeholder sales processes involving technical and executive buyers
- Ability to engage credibly with both technical practitioners and senior business leaders
- Experience collaborating with a Sales Engineer on sales cycles
- Strong account planning, discovery, and business case development skills
- Experience closing six-figure enterprise opportunities strongly preferred
- Experience using Gong or similar tools to collaborate internally and manage pipeline
- Location: Remote, but based in or near New York tri-state area, San Francisco Bay Area, or Seattle; occasional travel/commute within assigned region required
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
