Finance
Scaling with Tailscale from Pre-Seed to Post-Series C
From standing up finance infrastructure to fundraising and M&A
Introduction
Tailscale provides a zero-configuration VPN for building secure networks. BrightIron was the company’s first accounting partner (Bookkeeping and Controller) when they had fewer than 5 employees. BrightIron has supported the company through multiple capital raises over the past 3 years, including their $100M USD Series B and $160M USD Series C.
The Challenge
Tailscale was experiencing rapid growth and needed robust financial operations to support their expanding business. They lacked a cohesive finance technology stack and required a structured chart of accounts tailored to strategic decision-making.
Additionally, Tailscale faced challenges in managing accurate financial transaction entry, payroll processing across Canada and the US, and creating clear accounting policies, particularly around revenue recognition. Effective reporting for subsidiaries, consolidated financial statements, Board and investor communications, and timely tax filings were also pressing concerns.
Our Solutions
BrightIron partnered closely with Tailscale to build a comprehensive financial infrastructure. We implemented QuickBooks Online and integrated a tailored finance tech stack, including Stripe, Expensify, Ceridian, Mosaic, and BambooHR, streamlining their operations significantly.
BrightIron developed and implemented a customized chart of accounts, enabling Tailscale’s leadership to access precise, actionable data for informed decision-making. Our team meticulously entered all financial transactions into QuickBooks Online, ensuring accuracy and timeliness. We also created and established clear accounting policies, particularly around revenue recognition, to maintain compliance and accuracy in financial reporting.
Our team handled payroll processing seamlessly across both Canadian and US operations. BrightIron provided detailed subsidiary and consolidated financial reporting, along with comprehensive support for Board and investor communications. Finally, we managed the company’s tax filings, ensuring all obligations were met promptly and accurately, further reducing operational risk and complexity for Tailscale.
Our role with the company continued to evolve as Tailscale grew. It started with BrightIron managing the entire finance function to eventually augmenting the company’s in-house finance team as they continued their rapid growth.
“This is actually the second company at which I’ve worked with BrightIron and they’d be my first call if I ever need another fractional firm to work with again in the future.”
David Carney
Co-Founder, CEO, Tailscale
