Business Operations & Strategy Manager

Tailscale

3h • CA$166,160 - CA$241,200 • Remote

About The Position

The Business Operations & Strategy team is Tailscale's embedded operator for the most significant cross-functional problems that don't have a natural owner, or that are critical to the long-term success of Tailscale – we diagnose, we implement, and we hand off durable solutions so the company doesn't have to solve the same problem twice. We're looking for someone both highly competent and highly curious -- the kind of person who isn't satisfied with "good enough," and who won't leave a known problem unfixed. We're a small, high-leverage team working at the intersection of commercial strategy, operational infrastructure, and company-wide execution. The scope of this role reflects that mandate: things like commercial strategy, international expansion, improving business systems, pricing architecture — work that's critical enough that someone has to own getting it across the finish line. If you thrive on ambiguity, care deeply about getting things done, and want to see a direct line between your work and the company's trajectory, please apply. This position reports to the Senior Manager of Business Operations & Strategy.

Requirements

• 4+ years of experience in business or strategy operations, strategy consulting, investment banking, venture capital, or a similarly analytical and execution-oriented role at a high-growth tech company
• Demonstrated ability to own complex, cross-functional projects from diagnosis through to completion (not just analysis and recommendations)
• Strong quantitative skills; comfortable doing your own data analysis without needing a dedicated analyst
• Familiarity with SaaS business models, GTM systems, and how a B2B company generates and retains revenue
• Clear, concise written communication — much of the cross-functional work happens async and in writing
• High tolerance for ambiguity, paired with the judgment to know when to move and when to ask
• Intellectual curiosity and a low tolerance for leaving known problems unaddressed

Nice To Haves

• Actual first-hand experience using Tailscale — it only takes a few minutes to set up and will greatly strengthen your application!
• Experience at a PLG company and/or first-hand experience with popular PLG projects — we sell to developers, and understanding how they discover and adopt tools matters
• Experience at a Series C or similarly-sized tech company (200-500 employees)
• Experience with Salesforce, Snowflake, Looker, Hex, or similar GTM and analytics tooling
• Comfort with AI-assisted workflows and an instinct for where automation creates real leverage versus noise
• Experience at a company that has gone through a pricing transition, international expansion, or similar structural growth milestone

Responsibilities

• Reshaping our pricing and packaging strategy
• Expanding the company to APAC through Singapore
• Scoping and sizing new commercial opportunities
• Driving cross-company AI adoption initiatives
• Performing deep-dive data analysis to identify opportunities and mitigate challenges
• Partnering with RevOps to mature our GTM infrastructure
• Reducing rework and duplication in our business systems

Benefits

• 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).
• 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, and the United Kingdom. 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 $1000 USD to customize your workstation to make it your own.
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed