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Strategic Enterprise Account Executive

Tailscale· Sales
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Remote$350kfull-timePosted 4d ago

About the role

Founding Strategic Account Executive role focused on 10,000+ employee organizations (Fortune 1000 and Global 2000) to own and grow high-value enterprise opportunities, build executive relationships, and shape the enterprise sales motion for Tailscale.

Responsibilities

  • Own account strategy: Build account plans that connect customer priorities with opportunities across business units, geographies, and use cases
  • Create pipeline: Drive personalized outbound prospecting, partnering with SDRs and Marketing on coordinated account-based campaigns
  • Lead complex deals: Manage opportunities through negotiation and close, navigating long sales cycles, competitive pursuits, and complex buying processes
  • Build executive relationships: Earn trust with CIOs, CISOs, CTOs, and senior technical and business leaders while developing champions across the organization
  • Bring the right team together: Partner with Customer Engineering, GTM Engineering, Customer Success, Product, Engineering, executive leadership, Legal, and Finance to win and grow strategic accounts
  • Shape the playbook: Test approaches, share what works, and bring customer feedback to teams shaping Tailscale’s product and enterprise strategy
  • Execute with discipline: Maintain clear qualification, accurate forecasts, and actionable account and opportunity plans

Qualifications

  • 5+ years of success as a top-performing enterprise or strategic seller in early stage, high-growth environments
  • Proven success selling to organizations with 10,000+ employees and closing complex six and seven-figure SaaS deals
  • Proven track record of consistently achieving or exceeding annual performance targets, with demonstrated YoY growth and sustained results
  • The ability to earn executive trust, engage technical stakeholders, and navigate procurement, legal, and financial reviews
  • Strong business judgment, clear written and verbal communication, and a collaborative, accountable approach
  • Comfort with ambiguity and enthusiasm for building a sales motion while carrying a quota
  • Demonstrated commitment to CRM hygiene, including accurate opportunity management, pipeline tracking, and forecast reliability
  • Proven ability to lead value-based sales conversations and quantify business impact to build compelling ROI-driven business cases

Skills

Required:Enterprise salesExecutive relationship managementStrategic account planning

Benefits

  • An inclusive, flexible environment where you can be your authentic self.
  • A competitive total compensation package: base salary, equity incentive plan and variable commission
  • Comprehensive group benefits with no waiting period (health, vision, dental, and more) for you and your family
  • Remote first company with opportunities for in-person collaboration as noted in the job description
  • Employer-funded retirement contributions (401(k)-style plan) with matching up to 0.75% of eligible compensation
  • Company retreats, team off-sites, and collaboration across multiple regions
  • Professional development support up to $1500 USD annually plus mentorship and internal promotion opportunities
  • Paid time off and flexible PTO program
  • Build-your-own home office setup (laptop, internet reimbursement, workstation funds)
  • Paid parental leave program (20 weeks birth parents, 16 weeks non-birth parents)
Last updated Oct 22, 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
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