Run the Numbers

Today we’re talking about capital allocation, and how it’s one of the most powerful, yet least discussed, skills a CEO needs to learn.

Every CEO has three core jobs:

* Run a good company (Operations)

* Tell a good story (Investor Relations)

* Deploy capital effectively (Capital Allocation)

Most CEOs focus 80% of their time on the first two. Yet it's the third, capital allocation, that often has the highest leverage and the least guidance.

You can read more about this topic at lookingforleverage.com

This week’s podcast is brought to you by Campfire (www.campfire.ai)

We’ve all used legacy ERPs. Painful migrations, endless consulting fees, and even after you’re live, getting simple answers still means hours in spreadsheets.

Campfire fixes that. It’s the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.

I’m excited to see how they keep reimagining this space – and you should be too.

Check them out at www.campfire.ai.

If you’re an accountant, AI might be coming for your job, but today’s guest believes that there’s never been a better time to be in the profession. CJ is joined by Scott Spiegel, the COO and former CFO of the American Institute of Certified Public Accountants (AICPA). He has decades of experience in finance and leadership at the intersection of business, mission, and membership. He breaks down how the accounting profession has changed and what skills you need to embrace in order to thrive in today’s world. He also shares insights into the surprising overlap between accounting and sales, the soft skills required for a successful accounting career, and the business dynamics of nonprofits, which, contrary to public belief, can and do make money. He also tells the story about how he uncovered fraud before making his predictions for the future of accounting.

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LINKS:

Scott Spiegel on LinkedIn: https://www.linkedin.com/in/scott-spiegel-cpa/

American Institute of Certified Public Accountants: https://www.aicpa-cima.com/home

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

Mostly metrics:

http://mostlymetrics.com

RELATED EPISODES:

Netflix Co-Founder Shares the Secrets to Being a Great CFO -

Scoring Big: The Playbook for Nonprofit Financial Success with USA Hockey CFO Kelly Mahncke -

Budgeting Your External Facing Time as a CFO: Tipalti’s Sarah Spoja -

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:43) Sponsor – RightRev | Navan | NetSuite

(07:21) An Intro to the AICPA

(09:25) How the Accounting Path Has Changed in 20 Years

(13:37) The Talent Crunch and the Relationship Side of Accounting

(15:05) If You’re an Accountant, Your Job Is Sales

(16:02) Sponsor – Pulley | Brex | Aleph

(20:12) The Relationship Side of Sales

(23:00) Scott’s Personal Product Market Fit at AICPA

(24:55) Making Lateral or Downward Career Moves

(27:39) Fighting for the Role You Want

(30:48) Why Leaders Don’t Have To Know All the Answers

(33:57) A Nonprofit Can Make Money

(36:16) How AICPA Has Changed the Way They Recruit for Talent

(40:35) The Constraints That Come With Being a Nonprofit

(42:41) No Mission Without Margin

(44:35) AI in AICPA and the Accounting Industry

(49:14) Keeping Your Job in the Era of AI

(52:13) Stories About Fraud

(55:57) How Fraud Has Changed Over the Past 5 – 10 Years

(58:04) The Future of the Accounting Career Path

—

SPONSORS:

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit

https://www.rightrev.com

and schedule a demo.

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 https://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.

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: https://pulley.com/mostlymetrics.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

#accounting #AIAndAccounting #AICPA #FutureOfAccounting #FinanceCareers

M&A deals usually involve a vast amount of legal fine print, and small oversights can have very costly consequences. To help you navigate this, CJ is joined in this episode by Trey O'Callaghan, a partner in Tech, M&A, and Emerging Companies at Goodwin. Trey breaks down the strategic role M&A lawyers play throughout the deal process in terms of both legal and business advice to help avoid costly missteps. The conversation explores when to involve legal counsel, issues like sales tax and contractor classification, and common deal-killers such as IP ownership and unresolved co-founder disputes. Trey also explains why earn-outs are the most litigated part of M&A deals and how to handle them wisely. The discussion touches on the personal implications of M&A deals for CFOs and how to negotiate adequate compensation. Trey also covers non-compete and non-solicit agreements, and the importance of understanding working capital fluctuations.

—

LINKS:

Trey O’Callaghan on LinkedIn: https://www.linkedin.com/in/trey-o-callaghan-3196896a/

Goodwin:

https://www.goodwinlaw.com/

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

Mostly metrics:

http://mostlymetrics.com

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:12) Sponsor – Navan | NetSuite | Pulley

(06:55) The Types of Law Trey Specialises In

(10:08) When a Company Should Engage With an M&A Lawyer

(16:52) Sponsor – Brex | Aleph | RightRev

(21:24) Deals That Have Fallen Apart

(24:15) Unpaid Sales Tax as a Common, Solvable Issue

(25:27) Issues With Contractors and How To Solve Them

(27:08) Problems With IP Ownership

(28:37) Co-Founder Issues

(29:43) The Most Litigated Part of M&A Deals: Earn-Outs

(34:30) Choosing the Right Plan To Use To Sell the Company

(37:11) Deal Fatigue

(38:36) The TLDR on Earn-Outs

(39:57) The Ideal Mindset for the CFO During the Deal Process

(42:33) When and How To Negotiate Compensation as a CFO

(47:55) Understanding Working Capital Fluctuations

(52:25) Non-Competes: How They Work

(56:34) Considerations for Non-Solicits

(59:51) Closing Words for Anyone Doing an M&A Deal

—

SPONSORS:

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.

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.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.

#MandA #MergersAndAcquisitions #MandALawyer #earnouts #CFO

Over the past 30 years, the number of publicly traded companies in the U.S. has been sliced in half, falling from a peak of ~8,000 in the late '90s to just ~4,000 today.

That stat shocked me. I knew IPOs were a slow drip, but I didn’t realize that the number of companies being taken private was far out pacing the number joining the NYSE and NASDAQ ranks.

Today we discuss:

* Three structural changes in the capital markets that brought us to this point

* The rise of private credit

* How companies staying private changes your job as an operator or CFO

This week’s podcast is brought to you by Campfire (www.campfire.ai)

We’ve all used legacy ERPs. Painful migrations, endless consulting fees, and even after you’re live, getting simple answers still means hours in spreadsheets.

Campfire fixes that. It’s the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.

I’m excited to see how they keep reimagining this space – and you should be too.

Check them out at www.campfire.ai.

In the current tech landscape, everyone is experimenting with AI, but when it comes to finance, we tread more carefully. In this episode, CJ is joined by Amy Butte, the CFO of Navan, one of the most AI-forward travel and expense platforms in operation. Amy highlights how the company is weaving AI into its operating system, not just to summarize documents, but to manage financial workflows with real impact. With a career spanning Wall Street and Silicon Valley, Amy also discusses her journey from being the CFO of the New York Stock Exchange to her current role. She delves into her experiences as an audit chair and touches on the challenges and opportunities in building teams and navigating change. She also breaks down the dynamics of the build versus buy debate in the current tech space before sharing anecdotes about her unique experiences at the New York Stock Exchange and her perspectives on being a woman in leadership.

—

LINKS:

Amy Butte on LinkedIn: https://www.linkedin.com/in/amybutte/

Navan: navan.com/Runthenumbers

Extraordinary Women on Boards:

https://www.ewobnetwork.com/

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

Mostly metrics:

http://mostlymetrics.com

—

TIMESTAMPS:

00:00 Preview and Intro02:59 Sponsor – MUFG | NetSuite | Pulley06:52 Conferences and Networking09:09 How Navan Has Implemented AI12:17 Whose Responsibility Is It To Drive AI Adoption14:50 The Risks Involved in Using AI in Finance15:50 Navan’s New Bot “Miles”17:00 Sponsor – Brex | Aleph | RightRev | Navan22:31 The Operational and Financial Impact of Using AI at Navan23:36 CSAT Scores: Humans Versus Bots24:46 AI Within the Finance Department27:37 What an Audit Chair Does32:04 Using the Audit Chair Seat To Influence Business Outcomes33:33 Mentoring CFOs and Unlocking Opportunities As Audit Chair36:29 How To Become a Board Member or Audit Chair38:58 The Role of the Director Versus the Role of the Operator39:44 Building Teams and Empowering People48:48 Build Versus Buy in the Era of AI51:28 Partnering: Collaboration Versus Control53:07 A Story About the Security at the New York Stock Exchange55:36 Meeting the CEO of Merrill Lynch57:43 Leadership and Opportunities for Women in Finance1:00:37 Long-Ass Lightning Round: A Big Mistake1:01:31 Advice to Younger Self1:02:37 Finance Software Stack1:02:55 Craziest Expense Story

—

SPONSORS:

MUFG is a global banking powerhouse that provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. Accelerate your growth trajectory. Contact group head Bob Blee at [email protected] to find out more.

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.

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.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.

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.

#Navan #AIFinance #FinancialTransformation #AuditChair #WomenInLeadership

Elon Musk, Peter Thiel, Reid Hoffman, Max Levchin, David O. Sacks, Roelof Botha, Chad Hurley, Russel Simmons, and Jeremy Stoppelman are among those considered the “PayPal Mafia”. These are cofounders or early team members of PayPal who went on to found or invest in major tech companies like Yelp, Palantir, YouTube, Facebook, SpaceX, X, LinkedIn, Affirm, Airbnb, and others. In this episode, CJ is joined by Jimmy Soni, bestselling author of The Founders, which chronicles the early years of PayPal. He delves into some of the lesser-known aspects of PayPal's history. He sheds light on Peter Thiel's prediction of the dot-com collapse, why he advocated for the employment of Roelof Botha as CFO at the age of just 26, and his second-chance philosophy for hiring failures. The conversation covers PayPal’s “frenemy relationship” with eBay, how they convinced their users to advocate for them, and pivotal moments that influenced their IPO and sale. Tune in for unique insights into one of the most important "seed funds" in tech history.

—

LINKS:

Jimmy Soni on X (@jimmyasoni): https://x.com/jimmyasoni

Jimmy Soni on LinkedIn: https://www.linkedin.com/in/jimmysoni

The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley: https://www.amazon.co.za/Founders-Paypal-Entrepreneurs-Shaped-Silicon/dp/1501197266

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

Mostly metrics:

http://mostlymetrics.com

RELATED EPISODES:

How Upwork CFO Erica Gessert Drove 20 Points of EBITDA Growth in Just 3 Quarters:

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:12) Sponsor – Pulley | Brex | Aleph

(07:40) Jimmy’s Approach to Writing the Book

(08:56) An Intro to the “PayPal Mafia”

(10:57) The 1998 to 2002 Time Period

(12:36) Present-Day Successes of “PayPal Mafia” Members

(14:06) Challenges of Interviewing High-Profile Figures

(16:06) Sponsor – RightRev | Navan | NetSuite

(19:46) Comparisons to Other Influential Tech Groups

(21:05) PayPal, YouTube, and the Embed Strategy

(23:21) The Company’s $20 Referral Program

(27:10) Peter Thiel’s Prediction of the Dot-Com Collapse

(30:48) The Fallout From the Merger That Resulted in PayPal

(33:00) The Evolution of PayPal’s Business Model

(36:58) The Unique Skillset That Roelof Botha Brought to the CFO Role

(41:04)) Fraud-Fighting Techniques

(43:26) PayPal’s “Frenemy Relationship” With eBay

(47:10) Challenges Faced by PayPal That Modern Fintechs Still Grapple With

(49:13) How PayPal Made Its Users Advocates for the Business

(53:44) PayPal’s Talent Acquisition and “Misfits” Culture

(56:54) Peter Thiel’s Talent-Spotting Abilities and Second-Chance Philosophy

(1:00:12) The Outcome of the eBay Sale

(1:05:03) One of the Most Important “Seed Funds” in Tech History

(1:08:07) Advice for Moving From Fast Work To Slow Work

(1:11:18) Favorite Behind-the-Scenes Anecdote

(1:13:04) The Most Underrated Member of the “Mafia”

(1:14:04) One of the Most Pivotal Decisions Made

(1:15:03) Wrap

—

SPONSORS:

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.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.

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.

#PayPalMafia #JimmySoni #CAPTCHA #PayPal #fintech

Figma Figma just raised the bar for IPOs in 2025.

Today we break down their revenue, margins, retention, and potential valuation in the public markets.

You can find the full analysis in written form at:

https://www.mostlymetrics.com/p/figma-ipo-s1-breakdown

This week’s podcast is brought to you by Campfire (www.campfire.ai)

We’ve all used legacy ERPs. Painful migrations, endless consulting fees, and even after you’re live, getting simple answers still means hours in spreadsheets.

Campfire fixes that. It’s the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it’s been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.

I’m excited to see how they keep reimagining this space – and you should be too.

Check them out at www.campfire.ai.

In many companies, the CFO is more important than the CEO. And the majority of private equity-backed CFOs are actually not up to par. In this episode, CJ is joined by Scott Engler, of LinkedIn fame, to explain why he believes these bold statements to be true. Scott is the CEO and co-founder of Sync Executive Partners and the co-founder of PE-Xcelerate. He has decades of experience studying, recruiting, and coaching CFOs. He shares insights on the evolving role of the CFO, the many hats they wear, and which they should prioritise. He gives advice on how to navigate your relationship with your CEO, your PE sponsor, and other stakeholders, and provides some social profiling hacks that can help. The conversation covers the benefits of upside-down reviews and why not having a recommendation can be the smartest move, before examining the best way to get a CFO job at a PE-backed company, and how to negotiate equity packages.

—

LINKS:

Scott Engler on LinkedIn: https://www.linkedin.com/in/scottengler/

Sync Executive Partners:

https://www.syncexecutivepartners.com/

PE-Xcelerate:

https://www.pexcelerate.com/

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

Mostly metrics:

http://mostlymetrics.com

Looking for Leverage:

RELATED EPISODES:

So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means -

CFO of FloQast on Why Finance Teams are Data Curators:

“What’s in It for Me?” The Art of Storytelling in an IPO - with Monday.com CFO Eliran Glazer:

Inside the "Triangle of Doom”: How Great CFOs Navigate CEO and Board Dynamics:

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:20 ) Sponsor – Brex | Aleph | RightRev

(07:12) How the CFO Role Has Changed Over the Last Decade

(12:08) Why the CFO Needs To Drive the Pace

(14:49) Why Most Private Equity-Backed CFOs Aren’t up to Par

(16:36) Sponsor – Navan | NetSuite | Pulley

(20:07) The PE-Backed CFO Versus Hypergrowth VC CFO

(21:54) How Senior Leaders Are Incented To Play It Safe

(26:04) The Operational CFO: The CFO Becoming More of a COO

(28:41) Why the CFO Is More Important Than the CEO

(32:16) How a CFO Should Prioritize Their Many Roles

(34:46) The Importance of Being a Good Storyteller

(38:49) What an Upside-Down Review Is

(43:46) Why Not Having a Recommendation Can Be the Smartest Move

(49:50) The Hardest CFOs Are the Easiest To Influence

(55:37) The Art and Science of Managing Your CEO

(57:48) Social Styles Hack

(1:00:47) Working With Your CEO and PE Sponsor

(1:04:08) The Best Way To Get a CFO Job at a PE-Backed Company

(1:11:54) The State of Comp for PE-Backed CFOs in This Market

(1:13:16) Negotiating Equity Packages

(1:15:39) The Biggest Challenge for PE-Backed CFOs Today

—

SPONSORS:

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.

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.

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.

#CFO #CEOversusCFO #ChiefFinancialOfficer #PrivateEquity #ScottEngler

The number one thing listeners of the pod ask me for is to flip the script and let someone interview me. I’ve historically been reluctant to do it because it feels little self aggrandizing or whatever the term is. But you gotta give the people what they want.

On this episode my friend Mike Wu, founder of Hire Frame, interviews me on my transition to full time content creation. We talk about

* How I sold a company as CFO, and then fired myself immediately

* Why having supportive partners in any entrepreneurial endeavor is the real key to success

* How I came up with the idea for my second newsletter Looking for Leverage.

Mike’s a gracious host and shout out to him for letting me share this with my audience.

Mike’s Podcast: What Worked on Spotify | Apple | YouTube

Mike’s Company: Hire Frame

Run the Numbers is brought to you by Zenskar.

Zenskar is an AI-powered order-to-cash platform that automates billing, revenue recognition, and SaaS reporting — no spreadsheets, no engineering required. Built for modern B2B companies, Zenskar supports any pricing model: subscriptions, usage-based, or complex custom contracts.

Step into the future of finance today. Visit zenskar.com/rtn and book a demo!

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.

—

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

RELATED EPISODES:

CFO of FloQast on Why Finance Teams are Data Curators:

The $7 Million Wake-Up Call: Mastering Rebates for Profitability with Enable’s Nick Rose:

G2 CFO Chad Gold on Building A Durable Career as a Venture Backed Exec:

—

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.

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