Business Operations & Strategy

Tailscale
Remote (United States)Posted 23 February 2026

Job Description

<div class="content-intro"><p><strong>About Tailscale </strong></p> <p>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.</p></div><p><span style="font-size: 12pt;"><strong>Job Description</strong></span></p> <p>We are looking for someone who wants to help scale a high growth startup and work cross-functionally across Sales, Marketing, Customer Experience, Operations, Product, and Engineering. </p> <p>As companies scale quickly, needs and gaps can emerge, and we are looking for a high-functioning individual to help anticipate and solve challenges that may arise as we scale. You would take on a variety of projects helping to seed and structure areas of growth before projects grow to be undertaken by new people or teams. Personal humility and willingness to “give up your Legos” as the company grows will be a core part of the role. </p> <p>As an early-stage and fully remote company, we are looking for motivated individuals who are comfortable working asynchronously, and thrive in ambiguity.</p> <p><span style="font-size: 12pt;"><strong>Key Responsibilities</strong></span></p> <p>While projects can vary as the company evolves, below are a few examples of areas that the role could entail:</p> <ul> <li>Work with leadership to develop goals consistent with our strategic vision and track progress.</li> <li>Help design strategic board presentations and investor materials.</li> <li>Assist with crafting executive communication around all hands, offsites, external parties, etc.</li> <li>Help evaluate and reshape our pricing and packaging strategy. This may require gaining a deep understanding of new and existing product value, evaluating infrastructure costs, understanding and listening to customer feedback, and thinking about how to operationally simplify our business.</li> <li>Reduce duplication in our business systems and set up processes to streamline and merge systems.</li> <li>Help accelerate the use of AI tools at Tailscale.</li> <li>Simplify our procurement process and look for efficiencies.</li> <li>Help evaluate our international expansion strategy and help bring us into additional global markets. This can include examining our footprint globally and identifying regions that may be underserved and require more attention, as well as helping to coordinate efforts across functions to successfully expand into new markets.</li> <li>Help design, implement, and improve business processes and internal systems (example could be improving billing for the partnerships team).</li> <li>Own end-to-end special projects, from scoping to execution and measurement.</li> </ul> <p><span style="font-size: 12pt;"><strong>What We Are Looking For</strong></span></p> <ul> <li>2+ years of experience in Business or Strategy Operations at a high-growth tech company, consulting, investment banking, venture capital, private equity, etc. </li> <li>Excellent business and technical acumen and analytical skills</li> <li>Ability to manage effectively with ambiguity and manage multiple projects and stakeholders to prioritize and re-prioritize in a rapidly changing environment</li> <li>Strong situational adaptability in both written and verbal communication</li> <li>Excellent communication and stakeholder management skills, capable of conveying complex concepts in simple terms</li> <li>Strong partnership skills within the Operations organization as well as with cross-functional teams </li> <li>Highly analytical and comfortable with SQL, spreadsheets, basic modeling, and presentation making</li> <li>(Bonus) Yo ... (truncated, view full listing at source)