We encourage you to help us break that statistic! Tailscale is making safe connection effortless 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. We're seeking a talented and motivated full-time Program Manager to join our team. 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.

Spot trends across operational health data and translate them into clear insights on how EPD is doing and where improvement is needed.

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. 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.

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.

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. 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. 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. 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.

Tailscale's compensation package includes base salary, equity, and comprehensive benefits. CAN Pay Range$152,760—$191,620 CAD An inclusive, flexible environment where you can be your authentic self. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).

Take advantage of coverage for health, vision, dental, and more for you and your family! Remote first company —most of our teams work fully remotely. 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).

Some roles require in-office collaboration depending on team needs, which will be clearly noted in the . Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.

Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration. Support for your personal and professional development.

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. Paid parental leave program . We care about your life outside of work and encourage current parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates.

📌 Program Manager, EPD Operations (Winnipeg)
🏢 Candidate
📍 Winnipeg