Strategic Enterprise Account Executive

Tailscale

3d • Remote

About The Position

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

You will help define how Tailscale wins in the strategic enterprise market by developing outbound strategies, testing new approaches, and creating a playbook for future growth. You will report to the Director of Strategic Sales, work on a small collaborative team, and partner closely with executive leadership and teams across the business.

Requirements

• At least 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 or more employees and closing complex six- and seven-figure SaaS deals.
• A record of consistently achieving or exceeding annual performance targets, with demonstrated year-over-year growth and sustained results.
• Ability to earn executive trust, engage technical stakeholders, and navigate procurement, legal, and financial reviews.
• Strong business judgment and clear written and verbal communication, with a collaborative and 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.
• Ability to lead value-based sales conversations and quantify business impact to build compelling ROI-driven business cases.
• Strong technical acumen.

Nice To Haves

• Experience as an early sales hire or helping build a new enterprise sales motion.
• Experience selling infrastructure, networking, cybersecurity, developer tools, or cloud software.

Responsibilities

• Build account plans that connect customer priorities with opportunities across business units, geographies, and use cases.
• Drive personalized outbound prospecting and partner with SDRs and Marketing on coordinated account-based campaigns.
• Manage opportunities through negotiation and close, navigating long sales cycles, competitive pursuits, and complex buying processes.
• Build trusted relationships with CIOs, CISOs, CTOs, and senior technical and business leaders, while developing champions throughout organizations.
• Coordinate with Customer Engineering, GTM Engineering, Customer Success, Product, Engineering, executive leadership, Legal, and Finance to win and grow strategic accounts.
• Test sales approaches, share effective practices, and relay customer feedback to teams shaping Tailscale’s product and enterprise strategy.
• Maintain clear qualification, accurate forecasts, and actionable account and opportunity plans.

Benefits

• Base salary, equity incentive plan, and variable commission for quota-based roles.
• Comprehensive health, vision, dental, and other group benefits for employees and their families, with no waiting period.
• Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to an annual employer contribution equal to 0.75% of eligible compensation.
• $1,500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
• Flexible paid time off.
• Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.
• Monthly home internet reimbursement and $500 USD to customize a home workstation.
• Company-owned laptop choice (Mac or PC).
• Corporate co-working program, company retreat, team off-sites, and support for team travel and in-person collaboration.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed