Business Operations & Strategy Manager

Tailscale

3h • $124,000 - $180,000 • 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

• Competitive total compensation package (base salary, equity incentive plan, variable commission for quota-based roles)
• Comprehensive group benefits with no waiting period (health, vision, dental, etc.)
• Remote-first company with flexibility in work location
• Annual company retreat, team off-sites, and opportunities for in-person collaboration
• $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities
• Flexible, paid time off program
• Build-your-own home office setup (company-owned laptop, monthly home internet reimbursement, $1000 USD for workstation customization)
• Generous parental leave program (up to 26 weeks of parental leave top-ups)
• Support for accessibility and inclusion in the hiring process

What This Job Offers

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