Business Operations & Strategy Manager

Tailscale is building the new Internet 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. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Job Description

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.

Key Responsibilities

While projects can vary as the company evolves, below are a few examples of projects the Business Operations & Strategy team is working on or has worked on in the past:

• 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

What We Are Looking For

• 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 Have

• 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

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.