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Strategic Finance



Accounting & Finance
Canada · United States · Remote
Posted on Wednesday, August 30, 2023

About Tailscale

Tailscale builds software that makes it easy to connect and secure devices, no matter where they are. Every day, banks and multinational companies use Tailscale to protect their corporate networks. Hobbyists and start-ups trust Tailscale to collaborate and share access to tooling. We're building a future for the Internet that's easy, small and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, HeavyBit, and Uncork Capital.

Job Description

We are looking to build out our strategic finance team here at Tailscale. This individual will be the first member of the team, reporting directly to the VP of Finance, and help drive our financial model, go to market strategy, and unit economics, alongside other strategic priorities as Tailscale grows.


  • Help drive the budget, operating model, and long-term financial plan for Tailscale
  • Perform analysis to support strategic decision-making around resource allocation and prioritization; identify areas for growth and improvement
  • Work with cross-functional leaders to influence strategic projects including pricing, unit economics, customer segmentation, and sales compensation
  • Build business cases for areas Tailscale should invest resources effectively
  • Drive alignment on KPIs and key metrics to track team-specific and company-wide trends, go-to-market initiatives, business performance, and provide visibility into operating performance
  • Prepare presentations and analysis for our Board of Directors, Executive Team, and investors


  • Have 2+ years of experience including Investment Banking and experience working at a fast-paced start-up (ideally SaaS) in Strategic Finance or FP&A
  • Have strong proficiency with financial modeling and Excel; work with SQL a plus
  • Be highly analytical with the ability to translate between strategic business decisions and their quantitative implications
  • Have excellent communication skills with the ability to distill complex issues into structured frameworks and concrete action plans
  • Be highly entrepreneurial and comfortable working in a fast-paced environment with minimal guidance

What We Offer

  • An inclusive, flexible environment where you can be your authentic self. We recognize the impact diverse voices and backgrounds have on the growth of our people, our product, and our company. And that flexibility in how and when you work empowers our team to balance work and life.
  • A competitive total compensation package. This includes base salary and an equity incentive plan.
  • Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
  • Remote-first with the opportunity to work from anywhere—enjoy a change of scenery wherever you can get wifi and join our company retreats with fellow Tailscalars!
  • Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, leverage our conference budget to learn from experts in your field, or take advantage of mentorship, coaching, and internal promotion opportunities.
  • Paid time off and a healthy work-life balance. Take advantage of 4 weeks of vacation each year, uncapped sick time when you need it, and support for any situation life throws your way!
  • 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.