Director, APAC Go-to-Market - Tailscale

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. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

Tailscale is looking for a Director, APAC Go-to-Market to build and lead our GTM business in Asia Pacific, starting from Singapore. You will be responsible for turning the APAC opportunity into a meaningful, durable business by building pipeline, developing a partner ecosystem, winning strategic customers, and scaling the regional team.

This is a hands-on leadership role. You will set the regional strategy, recruit the initial team, and be directly accountable for commercial results. You will report to Tailscale’s President, Kevin Kotecki.

Key Responsibilities

• Own the APAC number: Accountable for regional pipeline creation and revenue growth. Establish targets, build plans, and maintain forecasting discipline.
• Build and execute GTM strategy: Determine which markets, segments, and routes to market offer the greatest opportunity. Adapt global strategy for the APAC region.
• Build a high-performing organization: Recruit and lead exceptional talent across Sales, Solutions Engineering, and Partner Marketing.
• Lead from the front: Engage directly with strategic customers, build relationships with senior leaders, and serve as an executive sponsor.
• Establish regional presence: Represent Tailscale at industry events and within the broader technology ecosystem.
• Voice of APAC: Provide market intelligence to global Product, Marketing, and Engineering teams to influence company-wide decisions.
• Long-term scaling: Identify necessary investments and build systems that scale beyond the initial phase.

What We Are Looking For

• Significant experience in enterprise technology GTM, with a track record of leading Sales or GTM organizations across APAC.
• Proven experience building or materially scaling an APAC business from scratch.
• Deep familiarity with the APAC technology market, particularly Singapore and Southeast Asia.
• Established relationships within the regional channel and partner ecosystem.
• Strong network of GTM talent and the ability to attract high-performers.
• Experience selling highly technical products (infrastructure, networking, security, or developer tools).
• Strong analytical ability regarding pipeline math, unit economics, and market prioritization.
• A builder’s mindset: comfortable with ambiguity and capable of introducing structure without slowing the organization down.

What We Offer

• Competitive Compensation: Base salary, equity incentive plan, and variable commission.
• Comprehensive Benefits: Health, vision, and dental coverage with no waiting period.
• Remote-First Culture: Work from anywhere with a monthly home internet reimbursement and a $500 home office stipend.
• Professional Development: $1,500 USD annually for your growth.
• Retirement Support: Employer-funded retirement contributions (up to 0.75% of eligible compensation).
• Paid Parental Leave: 20 weeks for birthing parents, 16 weeks for non-birthing parents.
• Connection: Annual company retreats, team off-sites, and support for intentional in-person collaboration.