350K–350K USD / year
Strategic Enterprise Account Executive
SalesRemote — unknown
Published on 2026-10-17
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About this role
Own and grow a portfolio of large enterprise accounts, leading complex sales opportunities from prospecting through close and expansion. Help establish Tailscale’s strategic sales approach by testing outbound strategies, developing a playbook, and bringing customer feedback to the business.
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.
The team
Founding member of the Strategic Sales team, reporting to the Director of Strategic Sales.
What you'll do
- Develop account plans across business units, geographies, and use cases
- Create pipeline through personalized outbound prospecting and coordinated account-based campaigns
- Lead complex enterprise opportunities through negotiation and close
- Build relationships with executive and technical stakeholders
- Coordinate internal teams to win and expand strategic accounts
- Develop the strategic sales playbook and share customer feedback
- Maintain accurate opportunity plans, pipeline tracking, and forecasts
What we're looking for
- 5+ years of top-performing enterprise or strategic sales experience in an early-stage, high-growth environment
- Track record selling to organizations with 10,000+ employees and closing complex six- and seven-figure SaaS deals
- Consistently achieved or exceeded annual sales targets, with year-over-year growth
- Able to earn executive trust and navigate technical, procurement, legal, and financial reviews
- Strong communication, business judgment, collaboration, and accountability
- Comfortable with ambiguity and building a sales motion while carrying a quota
- Disciplined CRM and forecast management
- Able to lead value-based sales conversations and quantify business impact
Nice to have
- Experience as an early sales hire or building a new enterprise sales motion
- Technical acumen; experience selling infrastructure, networking, cybersecurity, developer tools, or cloud software
Benefits
- Equity incentive plan and variable commission
- Health, vision, and dental coverage with no waiting period
- Remote-first work and coworking program
- Employer retirement match up to 0.75% of eligible compensation
- Flexible paid time off
- Annual professional development budget of $1,500
- Company laptop, monthly internet reimbursement, and $500 home-office budget
- Paid parental leave: 20 weeks for birthing parents and 16 weeks for non-birthing parents