[Hiring] Strategic Enterprise Account Executive @Tailscale

Role Description

Tailscale makes it simple for organizations to securely connect people, devices, and workloads anywhere in the world. As adoption grows within the world’s largest enterprises, we’re launching a Strategic Sales team to support our next stage of growth.

As a founding Strategic Account Executive, you’ll own a focused portfolio of organizations with 10,000+ employees, including Fortune 1000 and Global 2000 companies. You’ll lead complex opportunities from initial engagement through close and expansion, building executive relationships and connecting customer priorities with Tailscale’s capabilities.

You’ll help define how we win in this market - developing outbound strategies, testing new approaches, and creating a playbook for future growth. Reporting to the Director of Strategic Sales, you’ll join a small, highly collaborative team and partner closely with executive leadership and teams across the business.

Key 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.

Preferred Experience

• Serving as an early sales hire or helping build a new enterprise sales motion.
• Candidates must have strong technical acumen. Background in selling infrastructure, networking, cybersecurity, developer tools, or cloud software is a bonus.

What We Offer

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package, including base salary, an equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family.
• Remote first company - most of our teams work fully remotely.
• Employer-funded retirement contributions, matching your retirement contributions dollar-for-dollar.
• Connect with other Tailscalars IRL through annual company retreats and team off-sites.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Flexible, paid time off program to support work-life integration.
• Build-your-own home office setup with a company-owned laptop and $500 USD to customize your workstation.
• Paid parental leave program with top-ups for birthing and non-birthing parents.