[Hiring] Enterprise Account Executive @Tailscale

Role Description

Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.

As an Enterprise Account Executive, you will be responsible for helping some of our largest clients and prospects to evaluate, purchase, and expand their usage of Tailscale as a solution to their company’s evolving networking, security, and compliance objectives. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.

We're an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers' needs. We are one of the fastest-growing VC-backed Dev Tool companies and are looking for folks to help us get to our next stage of growth. You will join a team helping define the future of secure connectivity and modern networking. Tailscale's product-led growth has created significant enterprise demand from organizations looking to simplify network access, strengthen security, and accelerate developer productivity. As an Enterprise Account Executive, you will work with some of the world's most sophisticated technology organizations to help them modernize legacy networking and security infrastructure.

Key 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.

Requirements

• Location: Remote, but based in or near the New York tri-state area, the San Francisco Bay Area, or Seattle.
• This role supports customers in one of three territories—New York and the Mid-Atlantic, the Bay Area, or the Pacific Northwest—and requires occasional travel/commute within the assigned region.

What Success Looks Like

• Consistently exceed quota through a combination of self-generated pipeline, new customer acquisition, and account expansion.
• Establish trusted advisor relationships with Security, Infrastructure, and Engineering leaders.
• Successfully drive adoption from initial deployment to broader organizational standardization.
• Build a predictable pipeline through disciplined prospecting and strategic account development.

Benefits

• 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, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Paid time off and a healthy work-life integration with a flexible, paid time off program.
• A build-your-own home office setup with a company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD to customize your workstation.
• Paid parental leave program with top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).