Director, Strategic Sales

Tailscale is building the new Internet 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.

Tailscale is redefining secure networking by making it simple for organizations to securely connect people, devices, and workloads anywhere in the world.

At Tailscale, we're solving one of the most fundamental challenges in modern infrastructure: secure connectivity. Our product is loved by developers, trusted by IT and security teams, and rapidly expanding within some of the world's largest organizations. As adoption accelerates, we're investing in a Strategic Sales motion that matches the scale of our ambition. If you're excited by the opportunity to build, lead, and sell and want to define how a category-leading company wins the largest enterprises in the world, we'd love to talk.

As we continue moving up-market, we're launching a new Strategic Sales organization focused exclusively on the world's largest enterprises. We're looking for a founding Director of Strategic Sales to help build one of the most important growth initiatives at Tailscale. This is a rare opportunity to define how we engage Fortune 1000 customers, establish a new go-to-market motion, recruit an elite team, and help shape the future of Enterprise Sales at Tailscale.

This is not a traditional frontline management role.

You'll be a seller, coach, and builder, personally leading many of Tailscale's largest strategic opportunities while building a high-performing team of Strategic Account Executives focused on organizations with more than 10,000 employees.

You'll define territory strategy, build an outbound-first motion, recruit exceptional talent, establish repeatable playbooks, and create the operating cadence that becomes the blueprint for Strategic Sales at Tailscale.

Our Strategic Sales organization will operate like an elite SWAT team, small, highly collaborative, and focused on pursuing a select number of transformational customers. You'll work alongside Executive Leadership, Product, Engineering, Customer Engineering, Marketing, GTM Engineering, and Customer Success to win the company's largest opportunities.

Initially, you'll lead a team of approximately 3–5 Strategic Account Executives while continuing to personally own and close strategic opportunities. As the business grows, you'll play a central role in scaling both the team and the operating model.

This role reports directly to the Head of Sales and offers the opportunity to build a category-defining Strategic Sales organization from the ground up.

Build a New Business

• Build Tailscale's Strategic Sales organization from the ground up.

• Design the operating model, territory strategy, account segmentation, and engagement approach.

• Develop repeatable playbooks for winning the world's largest enterprises.

• Help shape the long-term vision for Strategic Sales as the business scales.

• Partner with executive leadership to influence go-to-market strategy for