Enterprise Account Executive

Tailscale; United States; Remote; USD 250,000 - 300,000; Full time

Benefits offered by this job

Remote first

Equity plan

Professional development stipend

Mentorship and coaching

Retirement contributions

Job summary

Tailscale is seeking an Enterprise Account Executive to lead strategic partnerships with the world’s most sophisticated technology organizations. You will manage the full sales cycle, from prospecting to closing, while collaborating with Solutions Engineering, Customer Success, and Product teams to drive value and adoption.

Based remotely in the US with NYC flexibility, you will develop account plans, build executive relationships, and navigate complex procurement and security reviews to meet

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.

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.

Skills

Closing experience

Enterprise sales

Account planning

Stakeholder management

Technical understanding

Gong

Quota attainment

Tools

Gong

Job description

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’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.

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

• 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

What We Are Looking For

• 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

Location: Remote, but based in or near New York City 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

Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets. US Pay Range (OTE) $250,000 - $300,000 USD

What We Offer

An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. A competitive total compensation package.

• This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period.
• Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company - most of our teams work fully remotely.
• Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you).
• Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore.
• We support intentional in-person connection through team travel and distributed collaboration.
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
• Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.