Technical Program Manager
@ Tailscale

Hybrid
CA$200,000
Hybrid
Full Time
Posted 23 hours ago

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XXXXXXXXX XXXXXXXXXXX XXXXXXX****** @tailscale.com
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Job Details

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. Founded in 2019 and fully distributed, Tailscale is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Job Description

We are seeking a talented and motivated full-time Technical Program Manager to join our team. You will work across teams to guide development work in a fully remote, early-stage company.

Key Responsibilities

  • Manage large-scale technical programs from inception to delivery.
  • Coordinate between Engineering, Design, and Product teams.
  • Define success criteria and track KPIs for programs.
  • Identify process gaps and implement improvements.
  • Partner with stakeholders and drive multi-team delivery.
  • Establish program-level governance and mitigate risks.

What We Are Looking For

The ideal candidate has 5+ years of TPM experience in a startup environment, with deep technical insight and familiarity with networking security, WireGuard protocol, Zero Trust Networking, Agile methodologies, and project management tools like Jira, Notion, and GitHub. Strong communication, independence, and ability to work asynchronously are essential.

What We Offer

  • Inclusive, flexible environment with remote-first work.
  • Competitive total compensation including equity and benefits.
  • Professional development funding and mentorship opportunities.
  • Generous home office setup and parental leave benefits.
  • Opportunities for in-person collaboration through annual retreats and co-working programs.

Key skills/competency

  • Technical Program Manager
  • Remote work
  • Agile
  • Networking security
  • WireGuard
  • Stakeholder management
  • Process improvement
  • Risk management
  • Cross-functional coordination
  • Startup environment

How to Get Hired at Tailscale

🎯 Tips for Getting Hired

  • Research Tailscale's culture: Study their mission and remote work practices.
  • Customize your resume: Highlight relevant TPM experiences clearly.
  • Showcase project successes: Detail impacts in past programs.
  • Prepare for technical questions: Review networking and Agile topics.
  • Follow application instructions: Include white papers or case studies.

📝 Interview Preparation Advice

Technical Preparation

Review Agile practices and TPM documentation.
Study networking security fundamentals and WireGuard.
Practice using Jira, Notion, GitHub tools.
Review case studies of technical program management.

Behavioral Questions

Describe conflict resolution in cross-team projects.
Explain working independently in a remote setup.
Discuss handling changing priorities effectively.
Share experiences in stakeholder collaboration.

Frequently Asked Questions