Technical Program Manager, Tailscale
CA$174.2-218.4k
+ Equity
A zero config VPN for building secure networks
Job no longer available
A zero config VPN for building secure networks
201-500 employees
Job no longer available
CA$174.2-218.4k
+ Equity
201-500 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- Ability to think on one’s feet, enjoy collaborating with highly technical teams, and be comfortable working asynchronously is essential
- 5+ years of experience as a Technical Program Manager (TPM) within Engineering, coordinating large, complex, multi-team technical programs
- Experience as a TPM in a startup environment: Ability to thrive in a fast paced environment with a high level of ambiguity and constant change
- Experience with networking security software concepts and terminology (NAT traversal, DERPs, DNS, ACLs) and authentication (SSO, OIDC)
- Familiarity with WireGuard protocol and Zero Trust Networking
- Experience diving deep into technical details while maintaining a high-level view of program status
- Experience building trust with engineering teams and driving technical changes through influence
- A proven track record for being detail-oriented with a demonstrated ability to self-motivate and follow through on initiatives
- Ability to give and process constructive feedback, as well as work independently
- Ability to communicate openly, supporting and championing innovation and inclusivity, in both written and verbal communication
- Proficiency in Agile methodologies and project management tools, such as Jira, Notion, and GitHub
What the job involves
- We’re seeking a talented and motivated full-time Technical Program Manager to join our team. You’ll work across teams to guide development work
- Because we’re an early-stage and fully remote company, we’re looking for an individual who can work independently to align the teams involved in building the product
- Manage large scale technical programs from inception through delivery, coordinating between Engineering, Design, and Product (EPD) to schedule and guide development of features in the Tailscale product and (over)communicate what’s planned to a remote-first team
- Define clear success criteria, track KPIs and ensure programs deliver measurable outcomes aligned with strategic goals
- Recommend and implement improvements based on program retrospectives, stakeholder feedback, research, and industry trends
- Identify process gaps within EPD and develop just the right amount of process to fill the gap: not too much, not too little
- Partner with stakeholders to define requirements, align priorities, and drive delivery across engineering, product, support, and GtM
- Champion continuous improvement initiatives to scale agility, visibility, and velocity across programs
- Assist in strategic planning through coordination with Engineering teams, iterating on planning processes including capacity, interrupts, and tech debt planning
- Establish and maintain program-level governance, including anticipating and mitigating risk & issues, managing dependencies, and driving resolution through collaborative problem-solving
- Manage large complex multi-team technical programs in partnership with external customers
Application process
- You should include these in your application:
- Your resume
- Any available white papers, case studies, or other publicly available material where your role as a TPM was essential in bringing the project to fruition
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received, with reviewers agreeing that it is easy to set up and a great tool for developers. The company plans to develop its product further by tackling the complexity of software and confronting operational problems that people face daily. Off the back of impressive 2025 funding, Tailscale is expanding its engineering, product and sales teams as well as its global reach, all to empower small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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