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Salary: USD 250,000 - 300,000 / annual
Tailscale is a secure networking platform built on WireGuard that helps teams securely interconnect people and devices. Founded in 2019 and fully distributed, the company is backed by top-tier VCs (Accel, CRV, Insight, Heavybit, Uncork Capital) and is one of the fastest-growing companies in the Developer Security space.
As an Enterprise Account Executive, you will own and grow a territory of enterprise organizations, driving both net-new customer acquisition and expansion opportunities. You will be responsible for helping large clients and prospects evaluate, purchase, and expand their use of Tailscale to meet their networking, security, and compliance objectives.
Key responsibilities include:
- Owning a territory of enterprise organizations and driving net-new acquisition and expansion
- Self-sourcing pipeline through outbound prospecting, cold outreach, and strategic account targeting
- Taking ownership of the full sales cycle from lead to close
- Developing strategic account plans identifying key stakeholders, 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 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 the Solutions Engineering team and collaborate with Customer Success, Support, Marketing, and Product teams. Success means consistently exceeding quota through self-generated pipeline 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
- Based in or near San Francisco to support customers and occasional travel/commute within the assigned region
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
