[Hiring] Business Operations & Strategy Manager @Tailscale

Role 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:

• Commercial strategy
• International expansion
• Improving business systems
• Pricing architecture

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.

Qualifications

• 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

Requirements

• 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
• 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

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package, including base salary, an equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family!
• Remote first company — most of our teams work fully remotely.
• Connect with other Tailscalars IRL through annual company retreats and team off-sites.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Paid time off and a healthy work-life integration.
• A build-your-own home office setup with a company-owned laptop and $1000 USD to customize your workstation.
• Generous parental leave program from your first day.