Serving SMB mid-market customers is one thing, but when you go upstream to enterprise sales, everything changes: go-to-market strategy, the sales process, how you structure deals, even how you define customer value. Today's guest, Andrew Casey, has helped scale four SaaS companies: ServiceNow, WalkMe, Lacework, and his current company, Amplitude. At ServiceNow, he worked closely with Snowflake’s Mike Scarpelli and Coatue’s David Schneider, and he was instrumental in establishing the company’s deal desk to support its sales motion. As an operationally focused CFO, he shares a wealth of knowledge on the importance of staying close to the customer, structuring deals that work for both sides, establishing transparency in usage-based pricing, aligning incentives and strategy in sales, the pros and cons of multi-year deals, the problem with auto-renewals and what to do instead, and how to adapt your go-to-market strategy when moving from SMB mid-market to enterprise.

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LINKS:

Andrew Casey on LinkedIn: https://www.linkedin.com/in/andrew-casey-6b14875/

Amplitude:

https://amplitude.com

ServiceNow:

https://www.servicenow.com

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

Mostly metrics:

http://mostlymetrics.com

RELATED EPISODES:

Gaining Strategic Advantage in Vertical SaaS With Guidewire's CFO, Jeff Cooper

"Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth

The Largest Software IPO Ever: How Snowflake Still Left Money on the Table

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TIMESTAMPS:

(00:00) Preview and Intro

(02:40) Sponsor – Tropic | NetSuite | Planful | Tabs

(08:45) Becoming an Operationally Focused CFO

(11:50) Staying Close to the Customer as a CFO

(16:37) Sponsor – Rippling Spend | Pulley | MUFG

(20:34) Running Towards a Challenging Market at ServiceNow

(24:15) How He Established the Deal Desk at ServiceNow

(26:13) Structuring a Deal That Works for Both Sides

(29:08) Transparency in Usage-Based Pricing

(32:39) A Client’s “Budget Problem”: Cash or Expense Issue

(36:42) Lessons From Building Out the Deal Desk at ServiceNow

(40:53) Pros and Cons of Multi-Year Deals

(43:57) Auto-Renewals: Do This Instead

(46:10) Adapting the Go-to-Market Strategy for Enterprise Sales

(55:33) Selling to CIOs Whose Jobs Are at Stake

(58:18) What Defines “Enterprise”

(59:43) The Most Important Thing To Get Right in Enterprise Sales

(1:01:01) Lessons From Andrew’s Background in Corporate Finance

(1:03:12) The Story of How Andrew Got His Job at ServiceNow

(1:07:57) Long-Ass Lightning Round: A Big Mistake

(1:10:31) Advice to Younger Self

(1:11:17) Finance Software Stack

(1:14:47) Craziest Expense Story

—

SPONSORS:

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.

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.

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.

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.

#SMBtoEnterprise, #gotomarketstrategy #scalingSaaS #dealdesk #ServiceNow

Chime, the consumer fintech powerhouse, just filed to go public on the NYSE. On this podcast we’ll cover everything you need to know before they hit Wall Street👇This is a fintech that: → Doesn’t take deposits → Doesn’t lend off its balance sheet → Still did $1.67B (+31%) in revenue last year, mostly from swipe feesIt’s built for the 70% of Americans who live paycheck to paycheck — and earns their trust (and interchange) by becoming the #1 card in their wallet.But here’s the tradeoff:

✅ 88% gross margin ✅ 54 transactions per member per month ⚠️ MyPay credit losses nearly wiped out its new revenue stream ⚠️ Margins are getting squeezed (transaction margin dropped from 79% to 67% YoY)The IPO math? 📉 Valuation whispers = $8B–$9B (down from their $25B Series G, 2021) 📈 Forward revenue multiple = ~4x–5x 💡 Which makes Chime one of the most interesting public fintech comps in years.I unpack the full story — swipe economics, platform risk, and all — in this S-1 breakdown on Mostly Metrics.

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

To be a great finance leader, one needs to have both hard and soft skills. Today’s guest believes in running towards the hard market, asking dumb questions, and showing up as your whole self at work. Craig Conti is the EVP and CFO of Verra Mobility, the almost $900 million in revenue, publicly-traded company that is responsible for the silent infrastructure behind seamless tolling, traffic enforcement, and smart mobility. Apart from providing a visual breakdown of his approach to mitigating risk, he shares a wealth of wisdom from his years in finance. Hear about why Craig prioritizes investing in existing customers when it comes to capital allocation and how he explains Verra Mobility’s complex business model to non-finance people in the organization. This episode covers impostor syndrome, the difference between cost avoidance and cost savings, and why it may be more beneficial for you to work at a paper mill than at Apple, Meta, or Google.

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LINKS:

Craig Conti on LinkedIn: https://www.linkedin.com/in/craigcconti/

Verra Mobility:

https://www.verramobility.com/

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

Mostly metrics:

http://mostlymetrics.com

RELATED EPISODES:

Uncovering Blind Spots and Other Lessons from High-Growth Companies with Five-Time CFO David Lapter.

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:35) Sponsor – NetSuite | Planful | Tabs

(06:20) An Intro to Verra Mobility

(11:36) Continually Investing in Existing Customers

(14:47) Explaining Your Business Model When You Have Multiple Business Lines

(17:02) Sponsor – Rippling Spend | Pulley | Tropic

(21:10) A Tip for Orienting Outsiders to Your Business

(22:56) Decoding Finance for Non-Finance People in Your Org

(29:33) Cost Avoidance Versus Cost Savings

(31:00) How Having Resources To Reinvest Affects Capital Allocation Decisions

(34:12) A Skillset for Stepping Into New Roles: Stupid Questions

(38:55) Imposter Syndrome

(40:52) A Visual Framework for Mitigating Risk

(44:52) Known Risks Versus Unknown Risks

(46:07) Why Incentives Need To Align With Risk and Reward

(50:40) The Feedback Loop: Crisis Management to Future Risk Management

(52:16) Hard Skills Versus Soft Skills in Finance

(56:51) The Benefits of Bringing Your Whole Self To Work

(59:12) “Always Run to the Tough Market”

(1:03:34) “Life Comes Down to a Series of a Couple of Interactions”

(1:08:04) Long-Ass Lightning Round: Bad Hiring Decisions

(1:10:05) Advice to Younger Self: Move at Your Own Pace

(1:11:46) Finance Software Stack

(1:13:18) Craziest Expense Story

—

SPONSORS:

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.

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.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.

#financeleader #softskills #mitigatingrisk #capitalallocation #chieffinancialofficer

As a CFO, how should the way you navigate risk and return change from venture-backed companies to publicly-traded companies to private equity companies? To answer this question, CJ speaks with Mohit Daswani, a seasoned CFO with experience across multiple stages, including roles as CFO of Payments, Platform, and Risk at PayPal, and Head of Finance & Strategy at Square. Mohit shares the lessons learned from his time at Square, including when Jack Dorsey seeded a second billion-dollar business from within the company, and his experience at PayPal when they spun out from eBay under activist pressure. The conversation also covers the Rule of 40 in the different financial models, the dangers of using valuation as a scorecard, how founders should reset their mindset on what defines success, and the likelihood of a super app for the USA.

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LINKS:

Mohit Daswani on LinkedIn: https://www.linkedin.com/in/mohitdaswani1/

SimplePractice:

https://www.simplepractice.com/

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

Mostly metrics:

http://mostlymetrics.com

RELATED EPISODES:

From CF-No to CF-Go: Serial CFO Michael Bayer’s Guide to Hypergrowth:

Inside Grab: How a Super App Transformed Southeast Asia — with CFO Peter Oey:

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Timestamps:

(00:00) Preview and Intro

(02:42) Sponsor – Planful | Tabs | Rippling Spend

(06:36) Mohit’s Office and a Tip From Churchill

(09:07) Risk and Return in Different Investment Models

(13:05) Financial Discipline Versus Room for Growth in Venture-Backed Companies

(16:30) Sponsor – Pulley | Tropic | NetSuite

(20:25) Balancing Short-Term Performance and Long-Term Bets in the PE Space

(24:00) The Rule of 40 in Different Financial Models

(30:19) What People Get Wrong About the Private Equity Model

(34:40) The Benefits of Using Leverage

(37:41) The Dangers of Using Valuation as a Scorecard

(41:41) How Founders Should Reset Their Mindset on What Constitutes Success

(44:00) Being at Square When Jack Dorsey Seeded a Second Billion-Dollar Business

(49:43) Being at PayPal When They Spun Out From eBay

(53:59) PayPal’s Acquisition of Braintree

(55:48) The Probability of a Super App for the USA

(58:38) Learnings From Launching PayPal’s Payments Dongle in Japan

(1:04:12) Long-Ass Lightning Round: A Flight Mistake

(1:06:20) Advice to Younger Self

(1:07:31) Finance Software Stack

(1:09:28) Craziest Expense Story

—

SPONSORS:

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.

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.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.

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.

#VentureCapital #PrivateEquity #RiskManagement #RuleOf40 #PayPal

This is going to make all the PLG fan boys & girls angry...Today we talk about why Romanticizing PLG is dangerous.With AI companies hitting $50M ARR overnight (amazing product, credit cards, and a golden retriever named Kevin), a dangerous myth is spreading:👉 “You don’t need a sales team. The product sells itself.”Wrong. That was the dream of PLG. Now it’s become the CFO’s favorite excuse to avoid hiring reps. But romanticizing PLG as a cost-saving silver bullet? That’s corporate delusion.Some inconvenient truths:1️⃣ You cap your upside. Big logos don’t swipe the corporate Amex for $2M+ contracts. They send you to procurement purgatory. Hope you packed a snack.2️⃣ Credit card fees quietly bleed your margins. At $10M ARR, you could be giving $270K to Stripe instead of hiring 4 support reps.3️⃣ You stop talking to customers. Self-serve is great until you realize your roadmap is built on "watching" your customers from afar, and not feedback.4️⃣ Even Slack hired salespeople. So did Atlassian. So does every PLG darling with a pulse and a 10-Q.5️⃣ That “self-serve wedge into a $1B logo” slide? I’ve made that slide. I’ve been that guy. Truth is, it’s the law of large numbers—a narrative that is retroactively form fitted to the story you want to tell.PLG is a starting point. Not the whole playbook. If you want to scale past $25M ARR and sell to real enterprises, you need a sales team. You need relationships. You need to show up.Self-serve is a channel. Not an all encompassing strategy.PLG isn’t dead. But Santa PLG never existed.And if I had to bet, those founders and Kevin already hired a recruiter to staff up their CRO search.

Let’s dig in.

To explain why portfolio operations are increasingly the secret weapon in private equity, CJ interviews Paul Stansik. Paul is the writer of the Hello Operator Substack and Operating Partner at ParkerGale. He shares hands-on insights into how his team helps portfolio companies scale by transforming sales data into decisions, navigating post-acquisition go-to-market challenges, and driving the shift from being merely data-aware to fully data-driven. He also discusses sales teams, from hiring the right sales leader for each stage of growth to whether or not having a great playbook is important. With insights on the dangers of unspoken problems (“you can’t fix a secret”), how "templates build trust”, and how repeatable processes can unlock real commercial traction, this episode is packed with practical advice for CFOs, finance leaders, and operating partners.

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LINKS:

Paul Stansik: https://www.linkedin.com/in/paulstansik

ParkerGale:

https://www.parkergale.com

Hello Operator:

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

Mostly metrics:

http://mostlymetrics.com

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:52) Sponsor – Tabs | Rippling Spend | Pulley | Tropic

(09:18) What ParkerGale Capital Does

(11:35) Revenue Operations: Being the Keeper of the Standard

(17:05) Sponsor – NetSuite | MUFG | Planful

(20:34) Why Go-to-Market Teams Struggle To Provide More Data

(24:29) Data-Aware Versus Data-Driven

(26:54) Streamlining and Automating the Right Data

(29:56) Why Everything Being Okay Is a Signal That Something Is Wrong

(34:03) Defining Metrics and Why You Track Them

(40:18) The Qualities of Great Sales Leaders

(43:00) Why CEOs Often Pick the Wrong Sales Leader

(47:58) The Importance of Hiring Someone With a Good Playbook

(54:40) You Can’t Fix a Secret

(56:13) The Right Cadence for Reviewing Performance

(58:34) What Good Quota Attainment Looks Like

(01:01:02) The Lack of Training for Sales Teams

(01:03:54) The Urge To Promote the Best Sales Rep to People Manager

(01:07:10) Wrap

#PortfolioOperations #PrivateEquity #GoToMarketStrategy #DataDrivenDecisions #SalesLeadership

—

SPONSORS:

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.

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.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.

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.

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.

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.

The venture debt landscape has changed dramatically over the past few years, and CFOs can’t afford to be left behind. Catherine Jhung, Senior Managing Director at Hercules Capital and a seasoned expert in venture lending, joins CJ to explore the landscape of venture debt in 2025. Together, they unpack important questions for CFOs approaching lenders, the delicate balance between rate and flexibility, and a surprisingly overlooked use case for venture debt. You’ll also hear when not to raise debt, how to determine the right amount for your capital stack, what really separates banks from private debt funds, and the complex dance between VCs and debt providers. Plus, Catherine sheds light on the concept of capital as a commodity and how her early career in sales shaped her approach to selling the one thing every company needs: capital.

If you're looking for an ERP, head to NetSuite: https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

—

SPONSORS:

Rippling Spend is a spend management solution that handles your entire company’s spending in one unified system. It enables you to bring your corporate cards, expense management, bill pay, and more into one place to achieve real-time visibility and uniquely granular control with automated policy controls across every type of spend. 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. Trusted by companies like Linear and Runway, Pulley helps turn ownership into a strategic advantage. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. From spotting hidden optimization opportunities to automating painful procurement workflows and giving you the best market data to turn vendor negotiations in your favor, Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how.

NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics.

Tabs is the AI-native platform automating contract-to-revenue for fast-growing finance teams. Whether you're working with custom terms, usage-based pricing, or hybrid sales models, Tabs eliminates manual reconciliations and late-night deadlines, giving you clean, automated revenue data from contract to cash. Companies like Cortex and Statsig trust Tabs to streamline invoicing, rev rec, and cash application. Find out more at: tabs.inc/metrics.

—

LINKS:

Catherine Jhung on LinkedIn: https://www.linkedin.com/in/catherine-jhung-she-her-434732/

Hercules Capital:

https://www.htgc.com/

Ventured Growth: https://www.htgc.com/category/podcast/

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

Mostly metrics:

http://mostlymetrics.com

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:35) Sponsor – Rippling Spend | Pulley | Tropic

(07:29) The Questions CFOs Should Be Asking Lenders in 2025

(09:31) Three Plans CFOs Should Have When Approaching a Lender

(12:26) The Levers of Pricing and Flexibility

(14:45) Sponsor – NetSuite | Planful | Tabs

(18:50) How Hercules Differs From a Bank

(22:30) A Great Use Case for Venture Debt That Founders Rarely Think About

(23:47) Determining the Appropriate Amount of Debt for a Capital Stack

(27:38) When Not To Raise Venture Debt

(29:23) The Major Players in the Venture Debt Landscape Today

(31:37) Syndicated Deals Between Banks and Private Debt Funds

(35:15) VCs Versus Venture Debt Firms

(39:07) Building Relationships in the Venture Ecosystem

(39:06) Catherine’s History in Sales

(42:43) A Sales Skill That Made Catherine a Better Investor

(46:57) How To Differentiate Selling Capital as a Commodity

(49:22) What Catherine Learned About Finance and Leadership From Her Podcast

This past week I spoke to a group of 50 CFOs at Premji’s CFO Conference. I gave a presentation on how CFOs are using AI to improve efficiencies internally.

There’s a lot of information on how to build AI into your product, but not nearly enough on how to use it internally within your company to drive results.

Today I’ll take you through that presentation, and a survey I conducted, to show you where AI is being leveraged, and if you are actually behind.

For more on the topic visit: mostlymetrics.com

When it comes to investor relations, an organization’s communication strategy should be a key instrument to support its business strategy. While this may seem obvious, so often we get this wrong. In this episode, CJ hosts a masterclass on investor relations with Samuel Levenson and Jon Neitzell of the Arbor Advisory Group, focusing on the strategic role of IR in driving company valuation. They cover what “audience opportunity” really means and what to do when you've attracted the wrong investors. They talk about metrics, KPIs, and OKRs, plus why management credibility and conveying conviction can make or break your IR strategy. They also discuss what has changed in the IR profession over time and what hasn’t (but probably should) before suggesting changes you can make to drive impact immediately.

If you're looking for an ERP, head to NetSuite: https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

—

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. Trusted by companies like Linear and Runway, Pulley helps turn ownership into a strategic advantage. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. From spotting hidden optimization opportunities to automating painful procurement workflows and giving you the best market data to turn vendor negotiations in your favor, Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how.

NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics.

Tabs is the AI-native platform automating contract-to-revenue for fast-growing finance teams. Whether you're working with custom terms, usage-based pricing, or hybrid sales models, Tabs eliminates manual reconciliations and late-night deadlines—giving you clean, automated revenue data from contract to cash. Companies like Cortex and Statsig trust Tabs to streamline invoicing, rev rec, and cash application. Find out more at: tabs.inc/metrics.

Rippling Spend is a spend management solution that handles your entire company’s spending in one unified system. It enables you to bring your corporate cards, expense management, bill pay, and more into one place to achieve real-time visibility and uniquely granular control with automated policy controls across every type of spend. Get a demo to see how much time your org would save at rippling.com/metrics.

—

LINKS:

Samuel Levenson on LinkedIn: www.linkedin.com/in/samlevenson/

Jon Neitzell on LinkedIn: www.linkedin.com/in/jonathan-neitzell/

Arbor Advisory Group: www.arboradvisorygroup.com/

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

Mostly metrics:

http://mostlymetrics.com

—

TIMESTAMPS:

(00:00) Preview and Intro

(03:10) Sponsor – Pulley | Tropic | NetSuite

(07:53) How Your Communication Strategy Should Support Your Business Strategy

(10:38) Why You Should Speak to Different Investors Differently

(12:11) Defining “Audience Opportunity”

(15:24) Sponsor – Planful | Tabs | Rippling Spend

(19:18) What To Do if You Have the Wrong Investor Base

(22:16) Management Credibility and Conveying Conviction

(25:01) Metrics Your Investors Should Be Measuring

(32:42) The Metrics That You Should Disclose Versus Guide To

(35:45) The Science of the Story Versus the Art of the Story

(38:54) Actively Versus Passively Managed Assets

(40:50) Working Back to the OKRs That Drive the KPIs

(46:58) Why the IR Profession Hasn’t Changed Much Over Time

(51:11) The Shift in Communications in Recent Years

(54:05) Why Production Quality Is Important for Earnings Calls and Investor Days

(58:25) How IR Job-Related Technology Has Changed

(1:00:07) Changes To Make To Drive Impact Immediately

(1:04:23) “Data Transfers Conviction”

How does a surf forecasting platform evolve into a multi-pronged company with B2C subscriptions, advertising, B2B SaaS, and even some hardware? Dustan Berg, former equity analyst and current VP of Finance at Surfline Wavetrak, Inc., joins CJ to discuss the evolution of Surfline's business model and the nuances of running this 40-year-old startup. Dustan explains the role of data as a moat and how Surfline navigates retention and increasing wallet share in a business model that’s tied to user identity. He also talks about some of the frameworks he uses to maintain focus on strategy and what he learned about asking the right questions from his days as an equity analyst.

If you're looking for an ERP, head to NetSuite: https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

—

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. Trusted by companies like Linear and Runway, Pulley helps turn ownership into a strategic advantage. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.

Tabs is the AI-native platform automating contract-to-revenue for fast-growing finance teams. Whether you're working with custom terms, usage-based pricing, or hybrid sales models, Tabs eliminates manual reconciliations and late-night deadlines—giving you clean, automated revenue data from contract to cash. Companies like Cortex and Statsig trust Tabs to streamline invoicing, rev rec, and cash application. If you’re still closing the books like it’s 2015, it’s time for an upgrade: tabs.inc/metrics.

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. From spotting hidden optimization opportunities to automating painful procurement workflows and giving you the best market data to turn vendor negotiations in your favor, Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit tropicapp.io/mostlymetrics to learn how.

NetSuite provides financial software for all your business needs. More than 40,000 companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform, head to NetSuite https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics.

Subscript is a modern billing and revenue recognition platform designed for SaaS finance teams that need flexibility and accuracy. From automated invoicing and dunning to compliant, transparent revenue recognition and real-time analytics, Subscript eliminates manual work, reduces errors, and gives you a single source of truth for all your financial data. Book a free demo at subscript.com.

Rippling Spend is a spend management solution that handles your entire company’s spending in one unified system. It enables you to bring your corporate cards, expense management, bill pay, and more into one place to achieve real-time visibility and uniquely granular control with automated policy controls across every type of spend. Get a demo to see how much time your org would save at rippling.com/metrics.

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LINKS:

Dustan Berg on LinkedIn: https://www.linkedin.com/in/dustan-berg-cfa-b7a58634/

Surfline:

https://www.surfline.com

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

Mostly metrics:

http://mostlymetrics.com

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TIMESTAMPS

(00:00) Preview and Intro

(02:34) Sponsor – Pulley | Tabs | Tropic

(08:18) How to Measure a Wave

(12:30) Intro to Surfline: A 40-Year-Old Startup

(16:36) Sponsor – Netsuite | Planful | Subscript | Ripling

(21:09) The Evolution of Surfline’s Business Model

(25:38) B2B SaaS and Hardware Versus Just B2C Subscriptions and Advertising

(28:01) Data as a Moat

(32:34) The Nuances of Running a B2C Model Versus a B2B Model

(35:07) Net Dollar Retention Versus Gross Retention

(39:18) How Surfline Defines an Active User

(40:22) Retention in a Business Model That’s Tied to User Identity

(43:41) Lessons on Asking Questions From a Former Equity Analyst

(45:38) Dustan’s Framework for Maintaining Focus on Strategy

(47:22) Talking About Business Versus Talking About Numbers

(51:05) Dustan’s Favorite Buffett or Munger Quote

(52:49) Long-Ass Lightning Round: A Formula Error on an Annual Plan

(54:00) Advice to Younger Self

(54:23) Finance Software Stack

(56:29) Craziest Expense Story