Remote opportunity at
TailscaleStrategic Enterprise Account Executive
Tailscale builds software that enables people and devices to connect securely from any location, catering to users ranging from individual hobbyists to large global corporations. Founded…
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About This Role
Tailscale builds software that enables people and devices to connect securely from any location, catering to users ranging from individual hobbyists to large global corporations. Founded in 2019, the organization operates as a distributed company backed by several major investors. As the enterprise customer base expands, the firm is establishing a Strategic Sales department. The company is seeking a founding Strategic Enterprise Account Executive to manage a dedicated portfolio containing…
Job Description
Tailscale builds software that enables people and devices to connect securely from any location, catering to users ranging from individual hobbyists to large global corporations. Founded in 2019, the organization operates as a distributed company backed by several major investors.
As the enterprise customer base expands, the firm is establishing a Strategic Sales department. The company is seeking a founding Strategic Enterprise Account Executive to manage a dedicated portfolio containing organizations with over 10,000 employees, including Fortune 1000 and Global 2000 entities. Operating in a remote capacity, this professional will guide complex sales opportunities from initial contact through negotiation, establish executive relationships, and help shape outbound strategies and growth playbooks. The role reports directly to the Director of Strategic Sales and involves collaboration with internal groups such as Customer Engineering, Marketing, Finance, and Legal.
This position suits an experienced enterprise seller who enjoys building sales motions from the ground up, navigating long sales cycles, and handling ambiguity while carrying a quota.
Responsibilities
- Build and execute account plans targeting opportunities across business units, geographies, and use cases
- Drive personalized outbound prospecting in collaboration with SDRs and Marketing
- Manage complex opportunities through negotiation, closing, and long sales cycles
- Establish trust with CIOs, CISOs, CTOs, and other senior leaders while cultivating internal champions
- Partner with internal cross-functional teams including Customer Engineering, Product, Legal, and Finance
- Contribute to the sales playbook by testing approaches and feeding customer feedback to strategy teams
- Maintain discipline in pipeline tracking, forecasting, and qualification
Requirements
- More than 5 years of experience as a top-performing enterprise or strategic seller within early-stage, high-growth settings
- Demonstrated history of selling to organizations with over 10,000 employees and closing complex six and seven-figure SaaS deals
- Consistent track record of hitting or exceeding annual performance targets with year-over-year growth
- Ability to build value-based sales cases, engage technical stakeholders, and navigate procurement, legal, and financial reviews
- Strong business judgment, written communication, and verbal communication skills
- Comfort with ambiguity and dedication to CRM hygiene and forecast reliability
Qualifications
- Prior experience serving as an early sales hire or assisting in the creation of a new enterprise sales motion
- Strong technical acumen with a background in selling infrastructure, networking, cybersecurity, developer tools, or cloud software
Core Skills
Benefits
- Base salary of USD 350,000 per year, accompanied by an equity incentive plan and variable commission
- Comprehensive group benefits for employees and families covering health, dental, and vision with no waiting period
- Employer-matched retirement contributions up to 0.75% of eligible compensation
- Paid time off designed to support work-life integration
- Annual professional development budget of USD 1,500
- Work-from-home setup including a choice of company-owned laptop, monthly internet reimbursement, and USD 500 for workstation customization
- Paid parental leave providing up to 20 weeks for birthing parents and 16 weeks for non-birthing parents
- Opportunities for in-person collaboration through annual company retreats, team off-sites, and corporate co-working access
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the location or remote policy for this role?
The posting indicates that Tailscale is a remote-first company where most teams operate fully remotely, though some roles may require in-office collaboration based on team needs.
What is the salary for the Strategic Enterprise Account Executive position?
The annual base salary for this position is USD 350,000, complemented by equity, variable commission, and comprehensive benefits.
What kind of background is preferred for applicants?
Candidates with a background in selling cybersecurity, networking, infrastructure, developer tools, or cloud software are preferred, along with experience helping to build an early-stage enterprise sales motion.
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