Software Engineer, Product Strategy (Contractor)

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 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.

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

• 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.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• 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 our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK.
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.