Strategic Enterprise Account Executive

Responsibilities

You will own a focused portfolio of large enterprise accounts, driving the full sales cycle from prospecting to negotiation and closing. You will also collaborate with internal teams to develop sales strategies and playbooks to support the company's growth.

Requirements

Candidates must have 5+ years of experience in strategic or enterprise sales, specifically within high-growth SaaS environments. A proven track record of managing complex deals and building relationships with executive-level stakeholders is required.

Skills

• Strategic sales
• Enterprise sales
• Account management
• Outbound prospecting
• Negotiation
• Pipeline management
• Executive relationship building
• Technical acumen
• SaaS sales
• Value-based selling
• CRM hygiene
• Business case development
• Account planning
• Sales forecasting
• Cross-functional collaboration

Benefits

• Health insurance
• Vision insurance
• Dental insurance
• Equity incentive plan
• Variable commission
• Retirement contributions
• Paid time off
• Professional development budget
• Home office setup
• Internet reimbursement
• Paid parental leave

About this role

Thank you for considering Tailscale. If this job description resonates with you, please apply. 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 i...

About Tailscale

Software Development · 201-500 employees · headquartered in Toronto, Ontario · founded 2019