250K–300K USD / year
Enterprise Account Executive
SalesRemote — San Francisco
Published on 2026-09-28
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About this role
The Enterprise Account Executive will be responsible for driving sales with large clients and prospects, guiding them in evaluating and purchasing Tailscale's secure connectivity solutions. This role involves building relationships with various stakeholders and managing complex sales processes while collaborating with multiple internal teams.
About the company
Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.
What you'll do
- Own and grow a territory of enterprise organizations
- Proactively self-source pipeline through outbound prospecting
- Take ownership of the full sales cycle from lead to close
- Develop strategic account plans
- Build relationships with key stakeholders
- Navigate complex enterprise sales cycles
- Position Tailscale as a strategic platform
- Drive adoption beyond the initial deployment
What we're looking for
- 5+ years of closing experience in a sales role
- Successful experience selling technical software solutions
- Proven track record of meeting or exceeding quota in enterprise sales
- Experience managing multi-stakeholder sales processes
- Ability to engage with both technical and business leaders
Benefits
- Comprehensive group benefits with no waiting period
- Employer-funded retirement contributions
- Paid parental leave program
- Support for personal and professional development
- Flexible paid time off program
- Build-your-own home office setup