The CFO software ecosystem is highly fragmented and ripe for disruption. Sean Jacobsohn, partner at Norwest, has a front-row seat to the action: He’s backed 10 companies selling to CFOs, while Norwest has invested in 20. Having identified 300 companies in 15 different categories operating in the space, he joins CJ to share takeaways from his market map of the evolving CFO software stack. They dig into what’s driving disruption, how new players are challenging legacy systems, and what it takes for founders to stand out. The conversation spans everything from the staying power of spreadsheets to the debate between building for verticals versus horizontals, the future of FP&A, and how AI agents might reshape the stack. Sean delves into the dynamics of partnerships, outlining five key rules for successful collaborations. Additionally, he talks about his Failure Museum which showcases a collection of items representing failed products and companies, and breaks down what he has identified as the six forces of failure.

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LINKS:

Sean Jacobsohn on LinkedIn: https://www.linkedin.com/in/seanjacobsohn

Norwest:

https://www.nvp.com

Market Map: Reimagining the CFO Software Stack: https://www.nvp.com/blog/market-map-reimagining-cfo-software-stack

Failure Museum:

https://failure.museum/

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

http://mostlymetrics.com

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TIMESTAMPS:

(00:00) Preview and Intro

(02:04) Sponsor – Rippling Spend | Pulley | Navan

(06:08) The Fragmentation of the CFO Tool Ecosystem

(07:24) Advice for Founders on Deep Domain Expertise

(10:39) Enable: Disrupting an Existing Solution Versus Creating a New Category

(12:32) The Prevalence of Spreadsheets in the Current Ecosystem

(13:39) Solutions Built for Verticals Versus Horizontals

(16:24) Sponsor – NetSuite | Planful | Tabs

(20:22) Vertical Software and the Move to the Cloud

(22:17) The Likelihood of Consolidation by Incumbents in the Space

(24:53) Developments in the FP&A Space

(26:55) The Future of AI Agents in Finance

(28:05) The Five Key Rules of Partnerships: Partner Fit

(29:17) Entering New Markets

(30:16) Enablement: The Importance of Training

(32:28) Reciprocation

(33:49) How Often the Little Guy Approaches the Big Guy in Partnerships

(34:51) M&A in Partnerships

(37:01) The Best Way To Form a Partnership

(37:45) The Inspiration Behind the Failure Museum

(39:14) The Six Forces of Failure

(40:38) Falling out of Product-Market Fit

(41:25 Examples of Failures From the Failure Museum

(44:58) How the Failure Museum Informs Sean’s Work at Norwest

(46:12) The Magic of Pivoting

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