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About the RoleWe'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.
Key ResponsibilitiesYou 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.
What We Are Looking For- 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.
As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.
CAN Pay Range
$152,760-$191,620 CAD
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!
- 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 job description.
- 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.
- Connect with other Tailscalars IRL. 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. 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 $500 USD to customize your workstation to make it your own.
- Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).
