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Tailscale is a secure networking platform built on WireGuard that helps organizations securely interconnect people and devices anywhere in the world. Founded in 2019 and fully distributed, the company is backed by top-tier VCs including Accel, CRV, and Insight.
You will be the founding Director of Strategic Sales, building Tailscale's new Strategic Sales organization from the ground up. This is a hybrid seller-leader role where you will personally own and close some of Tailscale's largest strategic opportunities while building and coaching a team of 3–5 Strategic Account Executives focused on Fortune 1000 enterprises (10,000+ employees).
Key responsibilities include:
**Build a New Business:** Design the operating model, territory strategy, account segmentation, and engagement approach for Strategic Sales. Develop repeatable playbooks for winning the world's largest enterprises. Partner with executive leadership to shape go-to-market strategy for major customers.
**Lead From the Front:** Personally manage a portfolio of Tailscale's highest-value strategic accounts. Lead complex, multi-stakeholder sales cycles from initial engagement through expansion. Develop trusted relationships with C-suite executives (CIOs, CISOs, CTOs, Chief Architects, Infrastructure leaders). Serve as executive quarterback on the company's largest pursuits. Negotiate complex commercial agreements across technical, financial, legal, and executive stakeholders.
**Build an Elite Team:** Recruit and develop exceptional Strategic Account Executives. Coach account strategy, executive engagement, negotiation, forecasting, and deal execution. Foster a high-performance culture built on accountability, collaboration, and continuous learning.
You'll work alongside executive leadership, product, engineering, customer engineering, marketing, and customer success. The Strategic Sales organization will operate as an elite SWAT team—small, highly collaborative, and focused on transformational customers. This role reports directly to the Head of Sales and offers the opportunity to define how a category-leading company wins the largest enterprises.
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
