Inside the CFO Tech Stack (and the Failure Museum): Insights From Norwest’s Sean Jacobsohn
Run the Numbers
Automating Financial Management and Enhancing Clarity
This chapter explores the challenges faced by CFOs in managing time-consuming financial tasks, presenting Rippling Spend as an automated solution for expense management. It also introduces Pulley for cap table management and Navon as a travel and expense solution, showcasing their unique benefits for listeners.
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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SPONSORS:
Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.
Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.
Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.
NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.
Planful’s financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you’ll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.
Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.
#CFOsoftware #marketmap #verticalSaaS #FPandA #FailureMuseum
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