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Enterprise Account Executive

Tailscale· Sales
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full-timePosted 3w ago

About the role

Enterprise Account Executive at Tailscale focusing on helping large clients evaluate, purchase, and expand usage of Tailscale for secure connectivity and modern networking. Remote role based near San Francisco with collaboration across Sales, Solutions Engineering, Customer Success, Support, Marketing, and Product teams.

Responsibilities

  • Own and grow a territory of enterprise organizations, driving both net-new customer acquisition and expansion opportunities
  • Proactively self-source pipeline through outbound prospecting activities, including cold outreach, strategic account targeting and networking
  • Take ownership of the full sales cycle from lead to close
  • Develop strategic account plans that identify key stakeholders, organizational priorities, technical initiatives, and expansion paths across the account
  • Build relationships with Security, Infrastructure, Engineering, Compliance, and Executive stakeholders to drive alignment and consensus throughout the buying process
  • Navigate complex enterprise sales cycles involving multiple decision-makers, procurement processes, security reviews, and legal negotiations
  • Position Tailscale as a strategic platform for secure connectivity and modern network access by helping customers understand both the technical and business value of the solution
  • Lead cross-functional account teams consisting of Sales Engineering, Customer Success, Product, Marketing, and Support to deliver exceptional customer outcomes
  • Drive adoption beyond the initial deployment by identifying opportunities for broader organizational usage and long-term account growth

Qualifications

  • 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 and working with a Sales Engineer on sales cycles
  • Strong account planning, discovery, and business case development skills
  • Experience closing six-figure enterprise opportunities is strongly preferred
  • Experience using Gong, or similar, to collaborate internally and manage pipeline
  • Location: Remote, but based in or near San Francisco as it supports customers and requires occasional travel/commute within the assigned region.

Benefits

  • An inclusive, flexible environment where you can be your authentic self
  • A competitive total compensation package (base salary, equity, variable commission)
  • Comprehensive group benefits with no waiting period
  • Remote first company with optional in-office collaboration depending on team needs
  • Employer-funded retirement contributions (matching up to 0.75% of eligible compensation)
  • Annual company retreat and team off-sites
  • Professional development allowance ($1500 USD annually)
  • Paid time off and flexible PTO
  • Build-your-own home office setup (laptop, home internet reimbursement, workstation stipend)
  • Paid parental leave program (20 weeks birthing parents, 16 weeks non-birthing)
Last updated Oct 1, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
Company profileWebsite

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