On this episode of Controllers Classified, host Erik Zhou sits down with Brad Silicani, COO of Anrok, to talk about his journey from Big Four accounting to leading operations at a fast-growing tech company.

The discussion begins by covering Brad’s transition from audit to client side, and highlights the myriad of roles he held at Dropbox. In his time there he was Controller, tasked with landing a sound revenue recognition method, Head of Tax, focused on developing the right international tax structure prior to IPO, and Treasurer, responsible for managing $2B in cash in a changing interest rate environment. In covering all this, Brad shares how these experiences set him up for success in his current role as COO at Anrok, highlighting why a background in accounting and finance makes him the operations leader he is today.

And of course, no modern finance conversation would be complete without tackling the AI revolution. Erik and Brad dig into how automation and AI are reshaping accounting, tax, and treasury functions—not just making processes smoother but fundamentally redefining the role of finance leaders. Whether you're a CFO- OR COO-in-the-making, or just someone who loves hearing behind-the-scenes war stories from hyper-growth companies, this episode delivers sharp insights and great conversation.

Key Quotes

“It was a big transition, being in an environment where I was around a bunch of accountants who knew the acronyms to being in a world where you had to communicate with people who had no experience or background in accounting.”
“Accounting in a startup - you have to work with what you have.”
“I genuinely think that tax drives a lot of how the world works. Getting exposed to tax strategy was like a light bulb moment for me. I understood why a business would make a decision about where to play their people, produce their products, why they would acquire a company and do it in a certain way.”
“My career goals changed from CFO to COO because I loved getting exposed to all of the different parts of a business.”

Time Stamps

(00:50) The journey into accounting
(02:04) Early career and experience at E&Y
(05:03) Joining Dropbox: revenue recognition methods
(06:54) Scaling Dropbox: tax challenges
(20:12) Transition to Treasurer and preparing for IPO at Dropbox
(21:49) Becoming COO at Anrock
(25:55) The evolution of financial software
(36:14) Finance leaders are are fun too

Links