Note: The job is a remote job and is open to candidates in USA. Tailscale is building a new Internet by delivering software that interconnects people and their devices securely. The Business Operations & Strategy Manager will lead critical cross-functional projects to enhance commercial strategy, improve business systems, and drive international expansion efforts.
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
Skills
- 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
- 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
Benefits
- An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
- A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
- 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- 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.
Company Overview
Tailscale is a software company that provides zero-configuration virtual private networks (VPNs) for secure connectivity. It was founded in 2019, and is headquartered in Toronto, Ontario, CAN, with a workforce of 201-500 employees. Its website is https://www.tailscale.com.