Technical Accounting Manager, Tailscale
CA$241-268k
+ Equity incentive plan
More information about location
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
101-200 employees
Be an early applicant
CA$241-268k
+ Equity incentive plan
More information about location
101-200 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- 7+ years of progressive accounting experience with a strong focus on revenue recognition and audit preparation, ideally in a fast paced SaaS or tech environment
- CPA with a public accounting background (Big 4 preferred)
- Deep understanding of U.S. GAAP, including ASC 606 and ASC 718, with experience drafting technical memos and accounting policies
- Proven success leading or supporting first-time audits and implementing accounting systems or processes
- Proficiency with revenue recognition tools such as NetSuite ARM or Zuora RevPro; bonus for experience with usage-based or hybrid SaaS models and B2B revenue streams
- Independent and proactive, with strong project leadership, adaptability to ambiguity, and a continuous improvement mindset
What the job involves
- Tailscale is a rapidly growing company on a mission to make secure, private networks easy to use and accessible to everyone. Our zero-configuration VPN solution helps teams and individuals securely connect their devices and services, regardless of their location worldwide
- As we scale, we're building a world-class finance team to support our growth, and we're looking for a capable Technical Accounting Manager to join us
- As the Technical Accounting Manager, you'll establish and enhance Tailscale's financial reporting and compliance foundation
- While leading technical accounting and our first financial audit, this role goes beyond memo writing. You'll also contribute to billing, revenue processes, and deal desk support, working cross-functionally with teams like Data, Sales, Product, and Legal to ensure compliance and operational efficiency
- Drive audit readiness, leading end-to-end preparation, documentation, and seamless coordination with external auditors
- Evaluate and interpret contracts to support ASC 606 compliance, including preparing revenue checklists, journal entries, and technical memos
- Streamline and enhance revenue and billing system logic and data flows to ensure operational accuracy and GAAP alignment
- Partner on deal desk strategy with Legal, Operations, and Sales to assess revenue implications of complex deals and support contract structuring decisions
- Oversee and refine accounting policies across revenue and SBC while providing insights to leadership
- Lead special projects that support the scaling of the finance function
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received with reviewers agreeing that it is easy to set up and a great tool for developers. The company plan to develop its product further by tackling the complexity of software and confront operational problems that people face daily. The company continues its expansion by empowering small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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