Finance Leadership at High-Growth SaaS Firms

Amartya Singh: Welcome to Inside the CFO Office. Today’s guest is Josh Rappoport, VP of Finance at Acumatica. With a background in private equity, venture capital, and SaaS, Josh brings a rare dual lens of investor and operator.

Josh Rappoport: I like to say I did my career backwards - starting as an investor before moving into finance leadership. At the core of it all is curiosity. I’ve always been fascinated by how businesses actually work, not just from a high-level view but deep into operations.

Amartya: You’ve led finance across fast-growing SaaS companies. What are your top priorities today?

Josh: First is GTM efficiency - understanding bookings and driving predictable revenue. Second, resourcing - aligning people to growth plans. And third, delivery cost - especially as AI changes software delivery. We need to understand these new cost structures deeply.

Amartya: You’ve worked both in an ERP company and with ERP customers. How has that shaped your finance philosophy?

Josh: Finance is no longer just about numbers - it’s about understanding the activity behind them. The job is to partner with the business, translate operational realities into financial insight, and communicate them in a language everyone understands.

Amartya: You said something that stuck - finance as the “Rosetta Stone” of the business.

Josh: Exactly. A great finance team translates between functions - engineering, marketing, sales - so the whole business speaks the same strategic language.

Amartya: Let’s talk about CFOTech. You sit inside a leading ERP firm - how do you see the tech stack evolving?

Josh: Tech is a tool. AI is a sharper tool. But without strong foundational understanding - what I call the “shoulders” to wield the tool - it’s ineffective. We can’t skip training the next generation by letting AI handle all the entry-level thinking. That would be a mistake.

Amartya: That’s a bold and thoughtful take. Last question - what advice do you have for finance professionals aiming to lead?

Josh: Three things:

Stay curious. “I don’t know” is the best starting point.

Communicate. Telling the story behind the numbers is more powerful than just showing the numbers.

Understand your stakeholders. Great finance strategy starts with understanding what people really want.

Amartya: Loved this conversation, Josh. Thanks for sharing your story and perspectives with us.

Josh: Thanks for having me. Conversations like this help me reflect and grow too.