Staff Accountant, Tailscale
$56-125k
+ 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
$56-125k
+ 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
- 3+ years of experience in Accounting, Deal Desk, or Order-to-Cash roles at SaaS high-growth startups
- Solid understanding of order-to-cash processes, SaaS billing models, and ASC 606 revenue recognition principles
- Experience with CRM (Salesforce), billing platforms (Stripe), and ERP systems
- Strong accounting foundation; CPA a plus
- Excellent organizational skills, with the ability to balance detail orientation and cross-functional collaboration
- Self-starter with an entrepreneurial mindset; comfortable working in a fast-paced, remote-first environment
What the job involves
- Tailscale is growing, and we’re looking for a detail-oriented and collaborative Staff Accountant to join our Finance & Accounting team
- In this role, you’ll oversee the full order-to-cash cycle — serving as the primary liaison with Sales to review and approve deals, ensuring they flow cleanly into billing, collections, and revenue recognition
- You’ll also support broader accounting processes, contributing to monthly close, reconciliations, revenue recognition, and general financial reporting
- This is an opportunity to play a pivotal role in building scalable financial operations, balancing the need for compliance and accuracy with the agility required in a fast-growing SaaS business
- Serve as the first point of contact from finance for Sales on deal structuring, order processing, and approvals
- Review and approve transactions to ensure compliance with company policies, contractual guidelines, and revenue recognition standards
- Maintain accurate deal setup in CRM, billing, and ERP systems to enable invoicing and revenue recognition
- Support the month-end close process, including revenue recognition in accordance with ASC 606 and account reconciliations
- Partner cross-functionally with Sales, Customer Success, and Legal to streamline workflows and reduce friction in the deal-to-cash process
- Monitor accounts receivable, support collections efforts, and help resolve billing disputes
- Assist with internal controls, process documentation, and audit support as needed
- Identify and implement improvements to increase efficiency and accuracy across order-to-cash and accounting processes
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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