Tailscale

You'll serve as a force multiplier across our high-velocity, product-led sales motion, working closely with Sales, SEs, Marketing, Product, and Customer teams. Your mission is to help our revenue teams consistently and confidently articulate the value of Tailscale to technical audiences, especially IT and engineering leaders. This role is ideal for someone who has experience selling or enabling technical tools and understands the IT/engineering persona.

Seeking a highly skilled and motivated Software Engineer to join our growing team. You will develop the Tailscale product, contributing to both open-source client code and related backend services, with an emphasis on networking features and optimizations. Take ownership of the entire product lifecycle, from writing code to product ideation and strategic decision-making.

As a Customer Success Engineer (CSE) at Tailscale, you’ll be the bridge between their technical capabilities and the needs of their most strategic customers. You will work directly with customers to ensure their success with Tailscale’s products, helping them get onboarded, driving their long-term adoption, and providing expert technical guidance throughout their journey.

Own and scale our paid marketing channels by managing and optimizing Tailscale’s investment across digital and physical channels, including SEM, paid social, out-of-home (OOH), and sponsorships. This high-impact role sits at the core of our go-to-market strategy and connects directly to self-serve and sales revenue goals. We are looking for someone with analytical sharpness to grow into a team lead as we scale.

You will provide guidance, mentorship, and career development for a team of software engineers. You'll contribute toward the success of our Product organization which includes Engineering, Product Management, and Design. As Engineering Manager, you will provide technical direction in projects as needed, as well as grow the technical leadership capabilities of the engineers reporting to you.

Join the Product Strategy team at Tailscale as a Software Engineer Contractor and demonstrate why Tailscale should be the default connectivity solution for AI/MCP environments by building compelling proof-of-concepts and enabling customer integrations. Develop proof-of-concept applications that showcase Tailscale as the ideal connectivity layer for AI agents and tooling, and work directly with customers to help plan & build integrations that highlight Tailscale's advantages.