Software Contractor, Product Strategy (AI/MCP Focus)

Employment Type: Contract

Location Type: Fully Remote

About Tailscale

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.

Job Description

We're seeking a skilled software contractor to join our Product Strategy team, reporting directly to the Chief Strategy Officer. You'll demonstrate why Tailscale should be the default connectivity solution for AI/MCP environments by building compelling proof-of-concepts and enabling customer integrations.

Key Responsibilities

• Develop proof-of-concept applications that showcase Tailscale as the ideal connectivity layer for AI agents and tooling (e.g. remote MCP servers).
• Work directly with customers to help plan & build integrations that highlight Tailscale's advantages.
• Create compelling demonstrations of secure, seamless MCP server connectivity via Tailscale.
• Engage with the Model Context Protocol community to evangelize Tailscale solutions.
• Build reference architectures showing Tailscale's benefits for AI infrastructure use cases.
• Document and communicate the strategic value proposition of Tailscale for MCP use cases.

Required Skills

• Strong proficiency in Go and / or Python (bonus TypeScript).
• Experience building integrations and working with third-party APIs.
• Experience using LLMs with day-to-day coding tasks as well as building tools or apps on top of LLMs.
• Ability to rapidly prototype and create compelling technical demonstrations.
• Strong storytelling skills to communicate technical value propositions.
• Customer-facing communication and presentation abilities.
• Comfortable working independently in a remote environment.

Preferred Experience

• Familiarity with Tailscale networking solutions.
• Experience with AI tooling and MCP server development.
• Background in developer tooling and/or solution architecture / engineering.
• Understanding of networking challenges in multi-cloud and hybrid deployments.
• Open source community participation.

What We Offer

• Competitive contractor rates.
• Flexible schedule and fully remote work.
• Travel opportunities to represent Tailscale at industry events.
• Direct impact on positioning Tailscale in the growing AI ecosystem.
• Opportunity to shape emerging AI connectivity standards.

This is a full-time contract position with potential for long-term engagement based on project needs and performance.

Please note: additional benefits listed below are not applicable to this role; they only apply to Tailscale's full-time exempt employees.

Company Culture & Values

• 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.
• All-remote with the opportunity to work from anywhere—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).
• Connect with other Tailscalars IRL. Attend o