Program Manager, Tailscale
EPD Operations
CA$152.8-191.6k
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
201-500 employees
Be an early applicant
CA$152.8-191.6k
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
- Experience as a Program Manager or Technical Program Manager (TPM), coordinating with stakeholders and cross-functional teams, particularly experience working closely within Engineering and with Product
- Experience as a Program/Technical Program Manager in a remote startup environment
- A deep, working understanding of the technical engineering space, including how engineering teams operate day to day, common workflows and tooling, and where technical and process friction tend to show up
- Experience owning operational health processes, such as bug tracking, incidents, reliability, or escalations, and using them to drive measurable efficiency gains
- Strong data skills, including building dashboards and reports in tools like Jira and Snowflake, and a solid understanding of how to read and interpret data
- Ability to spot trends in data and translate them into a clear story: what's happening, why it matters, and what should change, paired with the ability to design and implement the process changes needed to act on it
- Experience supporting planning cycles, project tracking, and recurring reviews, such as project status reviews or leadership roadmap and priority reviews
- A comfort level with ambiguity and undefined deliverables. You're motivated by taming chaos and improving how things run, not just shipping a fixed checklist
- A tactical, execution-first orientation: you're energized by hands-on implementation and getting things done, more than by high-level strategy or planning alone
- Experience working with Engineering, Product, and Design leadership, understanding their motivations and priorities, and using that to help move initiatives forward and communicate goals across the company
- 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
- Familiarity with Agile methodologies and project management tools, such as Jira, Notion and GitHub
- Familiarity with technical solutions, engineering practices, and the security and engineering lifecycle
What the job involves
- We're seeking a talented and motivated full-time Program Manager to join our team
- This is a tactical, implementation-focused role, hands-on in shaping how EPD (Engineering, Product & Design) operates, works together, and stays productive: building and refining the processes and rhythms that keep the org running, driving improvement initiatives over time, and owning the processes behind EPD's operational health
- You'll help the team understand trends and spot where improvements are needed
- 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
- A deep understanding of the technical engineering space (how engineering teams operate, where the friction points typically live, and what good looks like) is essential to being effective and credible in this role
- Ability to think on one's feet, enjoy collaborating with highly technical teams, operate comfortably in ambiguity without a clearly defined deliverable, and be comfortable working asynchronously is essential
- You will work as part of the TPM team to:
- Own the processes for bug tracking, incidents, reliability, and escalations, and continuously improve them to drive efficiency and progress toward EPD's operational health goals
- Spot trends across operational health data and translate them into clear insights on how EPD is doing and where improvement is needed
- Build dashboards and reports in tools like Jira and Snowflake that give EPD and the broader company visibility into operational health and progress
- Turn data into a clear story: what it's telling us, why it matters, and what needs to change, then design and implement the process changes to act on it
- Identify process gaps with EPD and proactively develop just the right amount of process to fill the gap: not too much, not too little
- Support planning activities and project tracking processes, helping keep them running smoothly and consistently across EPD
- Help run project status reviews, leadership roadmap reviews, and priority reviews, making sure the right information is ready and the right people are in the room
- Connect the dots across systems, processes, and teams, spotting where disconnected efforts overlap, conflict, or could be simplified, and acting on it
- Jump in on whatever initiative pops up in EPD that needs support, structure, or someone to help carry it forward, whether or not it fits inside a defined program
- Handle project retrospectives involving participants and stakeholders to understand what went well and what should be adjusted in future project work
- Seek opportunities to bring about ongoing improvement and simplification in business operating procedures and practices, leading to improved efficiency and effectiveness
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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