Strategic Enterprise Account Executive

WinsAbove; United States; Remote; USD 315,000 - 385,000; Full time

Benefits offered by this job

Remote first

Equity

Base + incentives

Home office stipend

Professional development allowance

Paid time off

Parental leave

Job summary

Tailscale is building a Strategic Sales team to support our next growth phase. 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 aligning customer priorities with Tailscale’s capabilities. This remote-first role reports to the Director of Strategic Sales.

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.

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.

Skills

Enterprise selling

Executive relationships

CRM hygiene

Forecasting

Negotiation

Communication

Job description

Thank you for considering Tailscale. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

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

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

What We Are Looking For

• 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

You’ll Thrive Here If You…

• Enjoy building from the ground up - creating account strategies, testing approaches, and shaping a playbook as you go
• Love opening doors and winning complex enterprise deals through executive relationships, technical curiosity, and teamwork
• Are energized by ambiguity and take initiative to create structure and momentum
• Bring the same focus and discipline to building pipeline as you do to navigating complex negotiations and closing strategic deals
• Want to help define how Tailscale wins and grows its largest enterprise customers

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. 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.

US Pay Range

$350,000 – $350,000 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.