Enterprise Account Executive - Tailscale

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

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 are looking for enterprise sellers who know how to create opportunities, not just manage them. You are comfortable building executive relationships, navigating complex organizations, and earning credibility with both technical and business stakeholders. You understand how to translate technical capabilities into measurable business outcomes and can lead customers through transformational technology decisions.

Key Responsibilities

• Territory Ownership: Own and grow a territory of enterprise organizations, driving both net-new customer acquisition and expansion opportunities.
• Pipeline Generation: Proactively self-source pipeline through outbound prospecting activities, including cold outreach, strategic account targeting, and networking.
• Full Sales Cycle: Take ownership of the full sales cycle from lead to close.
• Account Planning: Develop strategic account plans that identify key stakeholders, organizational priorities, technical initiatives, and expansion paths across the account.
• Stakeholder Alignment: Build relationships with Security, Infrastructure, Engineering, Compliance, and Executive stakeholders to drive alignment and consensus throughout the buying process.
• Deal Navigation: Navigate complex enterprise sales cycles involving multiple decision-makers, procurement processes, security reviews, and legal negotiations.
• Value Positioning: 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.
• Cross-Functional Leadership: Lead cross-functional account teams consisting of Sales Engineering, Customer Success, Product, Marketing, and Support to deliver exceptional customer outcomes.
• Account Growth: Drive adoption beyond the initial deployment by identifying opportunities for broader organizational usage and long-term account growth.

What We Are Looking For

• Experience: 5+ years of closing experience in a sales role.
• Domain Expertise: Demonstrated success selling infrastructure, networking, cybersecurity, cloud, developer tools, or other highly technical software solutions.
• Track Record: Proven track record of consistently meeting or exceeding quota in an enterprise sales environment.
• Sales Complexity: Experience managing complex, multi-stakeholder sales processes involving technical and executive buyers.
• Credibility: Ability to engage credibly with both technical practitioners and senior business leaders.
• Collaboration: Experience collaborating and working with a Sales Engineer on sales cycles.
• Strategic Skills: Strong account planning, discovery, and business case development skills.
• Deal Size: Experience closing six-figure enterprise opportunities is strongly preferred.
• Tools: 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.

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.

What We Offer

• Inclusive, Flexible Environment: An environment where you can be your authentic self, with flexibility in how and when you work.
• Compensation: A competitive total compensation package including base salary, equity incentive plan, and variable commission.
• Health Benefits: Comprehensive group benefits with no waiting period (health, vision, dental, and more).
• Remote-First Culture: Work fully remotely with corporate co-working program access (WeWork or similar) and virtual/in-person social events.
• Retirement Match: Employer-funded retirement contributions matching dollar-for-dollar up to 0.75% of eligible compensation.
• In-Person Connections: Annual company retreats, team off-sites, and travel support for distributed collaboration.
• Professional Development: $1,500 USD annually for professional development, plus mentorship and coaching.
• Paid Time Off: Flexible, paid time off program to support work-life integration.
• Home Office Setup: Choose your own company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD to customize your workstation.
• Parental Leave: Paid parental leave program with top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).