Run the Numbers

In this episode, CJ interviews Stephen Grist, a seasoned seven-time CFO, to discuss what a CFO should aim to accomplish in their first 100 days at a company. Stephen provides an extensive playbook. He covers assessing and shoring up a team, understanding cash drivers, and implementing necessary systems and processes. He also emphasizes the importance of evaluating potential exit strategies from the start and the need for strong FP&A support. The conversation dives into how to approach your first board meeting as an incoming CFO and the critical relationships you should build. Stephen also shares insights into forecasting R&D spend and breaks down the allocation between incubating, investing, and maintaining products. He offers advice on developing internal projects versus customer-funded projects, managing technical debt, and determining R&D payback benchmarks. Having led global teams, Stephen shares tips for building cross-border centers of excellence and discusses some of the challenges faced in such environments. Tune in for one of the most fascinating stories the podcast has featured to date, along with Stephen's expert advice and engaging storytelling.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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SPONSORS:

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

NetSuite provides financial software for all your business needs. More than 38,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

@Sjgrist (Stephen Grist)

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TIMESTAMPS:(00:00) Preview and Intro(02:16) Sponsor – Maxio| Leapfin(04:56) A CFO’s First 100 Days at a New Company(10:49) Building a Finance Team Versus Joining One(13:48) Sponsor – NetSuite | Mercury(15:31) The Need for an FP&A Team and Storytelling(19:16) How to Approach Your First Board Meeting(20:49) Important Relationships to Invest in as a New CFO(24:47) Puzzel’s Structure Within the Development Organization(26:22) Internal Research Versus Customer-Funded Development(29:17) Investing in Technical Resources(32:12) Deciding to Sunset Products(34:21) R&D Payback Periods and Benchmarks(36:06) Squaring Up Technical Debt(38:02) Tips for Building Centers of Excellence Abroad(42:53) Functions Most Commonly Moved Abroad(43:56) A Fascinating Anecdote About Managing Cross-Border Teams(47:00) Long-Ass Lightning Round: The French VAT Department(48:29) Waiting for the Right Role(49:13) Puzzel’s Current Digital Transformation(50:28) Craziest Expense Story: Breast Reduction Surgery

In this episode, CJ interviews Anthony “Tony” Boor, Executive Vice President and CFO of Blackbaud, who shares the unique path he took from working at a motorcycle shop in New Mexico to becoming a CFO. Tony reflects on his first management experiences and the lessons learned as he navigated his early career. The conversation dives into the evolving role of CFOs, particularly as they take on more GM responsibilities. Tony offers insights into Blackbaud's business model, its revenue layer cake strategy, and their expansion into verticals like payments, which sees over $100 billion processed through their platform annually. He discusses how they monetize this and secure a competitive edge. Tony also introduces his approach to efficiency metrics, including ARR per OTE, and elaborates on key financial concepts like EVA and ROIC. The interview explores his consolidation philosophy focused on simplifying, standardizing, and automating, and how this has played out at Blackbaud. Tune in to hear Tony’s insights on building the right team to propel a career forward in the long-ass lightning round and a fascinating embezzlement story.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today.

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 38,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro(02:05) Sponsor – Leapfin | Planful(04:05) Tony’s Early Career(08:49) The Changing Role of the CFO(13:32) The Evolution of Blackbaud’s Strategy(17:01) Sponsor – Mercury | NetSuite | Maxio(19:50) Blackbaud’s Customers(21:21) The Purpose-Built Nature of Blackbaud(24:45) Why Add Payments(32:02) Efficiency Metrics: ARR per OTE(35:41) Net Dollar Retention(37:34) Return on Invested Capital(39:40) Economic Value Added(40:42) Residual Cash Earnings(41:57) Consolidation and Blackbaud’s Pillar Model(45:16) Centralized Back Offices(51:07) Long-Ass Lightning Round: A Large Acquisition Mistake(52:53) Building the Right Team Underneath You(56:21) Craziest Embezzlement Story

Daniel Kang, VP of finance at Mercury, joins CJ for a dive deep into the nuances of annual planning. Dan talks about why if annual planning feels like a finance exercise, it is destined to fail and will feel like pulling teeth. He describes how to use this exercise to lead a broader strategic discussion about a company's direction for a process that is more impactful and less tedious. Dan also highlights that if you’re searching for big ideas during the annual planning process, there may be underlying issues with your company's roadmap or innovation processes. He touches on the idea that planning tends to expand to fit the time allotted, explains why most companies spend too much time on it, and warns against the trap of false productivity. The conversation delves into how the planning process evolves with a company's growth, including how to calibrate for each stage and ensure plans are actionable. Throughout the episode, Dan provides frameworks to streamline annual planning for a successful outcome.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

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.

NetSuite provides financial software for all your business needs. More than 38,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:12) Sponsor – Planful | NetSuite(05:17) Why Annual Planning Shouldn’t Feel Like a Finance Exercise(10:13) Prioritisation Versus Ideation(12:26) Identifying Constraints(15:16) Annual Planning and Looking at Spans of Control(16:05) Sponsor – Maxio | Leapfin(18:37) Driving Upfront Strategy Versus Just Finance(22:35) Understanding Your Product(24:56) Why Most Companies Spend Too Much Time Planning(27:31) Exercises in False Productivity(33:51) Calibrating Annual Planning for Each Stage of the Company(38:05) A Breakdown of Stages to Plan For(41:22) The Importance of Planning in Smaller-Stage Companies(43:26) Processes to Actualize Your Plans(45:19) The Part of the Plan That’s Likely to Break First(46:11) The Time It Takes to Hire Good Talent(47:25) Budgets Versus Actuals(50:38) Quick Hitters: Planning Mistakes, Forecasting for Interest, Tips and Tricks

In this episode, CJ sits down with Dr. Julie Gurner, the author behind the Substack Ultra Successful, to explore how top CEOs, CFOs, and entrepreneurs manage their ambition, goals, and self-talk. They examine if being hard on yourself necessary for success and Dr. Gurner shares helpful reframes that can be used to overcome negative self-talk. The conversation delves into the concept of “haunting agitation,” a term she uses to describe the hunger and ambition driving high performers. Building on this, she introduces the idea of empirical guardrails to keep one’s ambition in check. Dr. Gurner also breaks down the difference between “motivated” individuals and those who go “all in,” explaining how full commitment can lead to exponential growth. They touch on the surprising power of seemingly “boring” and discuss what the “build in public” movement gets wrong. Lastly, they talk about the art of saying no to opportunities that, while tempting, may distract you from your core focus. Tune in for expert advice on channeling your drive toward meaningful success.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC. 

NetSuite provides financial software for all your business needs. More than 38,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@DrGurner (Dr. Julie Gurner) 

SUBSTACK:

mostlymetrics.com (Mostly metrics)

drgurner.substack.com (Ultra Successful) 

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TIMESTAMPS:(00:00) Preview and Intro(02:56) Sponsor - Mercury | NetSuite(05:28) Overcoming Negative Self-Talk(08:51) Reframing Fear as Excitement(13:26) Haunting Agitation(16:59) Sponsor - Maxio | Leapfin | Planful(20:06) Being in Your Business Versus on Your Business(23:58) The Impact of Haunting Agitation on Relationships(26:51) Moving Goal Posts and Setting up Metrics(30:52) Hitting the Goal Versus the Feeling of Forward Momentum(32:09) Alan Greenberg’s PSDs and What That Means(35:15) The Motivated Versus the All-in(41:02) Hangups for Motivated People(43:02) The Sunk Cost Fallacy(45:23) The Worst-Case Scenario Question(48:02) “Protecting Downside” Versus Having a Plan B(49:12) The Rewards of Going All-in(52:02) The Strategic Advantage of Boring(55:48) What the “Build in Public” Movement Gets Wrong(57:13) The Art of Saying No to Good Opportunities(59:28) Overcoming People Pleasing(01:02:03) Wrap

In this episode, Joseph Floyd from Emergence Capital joins CJ to dive into the venture capital firm’s latest benchmarking report, offering insights into the enterprise software space. Compiled from over 650 responses from Emergence Capital’s portfolio and additional seed firms, the report covers a range of companies from pre-seed to pre-IPO. Joe discusses key trends in AI adoption, highlighting the contrast between companies incorporating AI and those actually generating revenue from it. The conversation also touches on efficiency metrics like net dollar retention rates, and whether the rule of 40 still holds relevance. Joe sheds light on the struggles faced by companies in the "messy middle," grappling with slower growth and burning cash. Other topics include the lengthening time between early-stage funding rounds, the shift in fundraising dynamics, and why some founders are rethinking their need for venture capital altogether. Tune in for a comprehensive look at the current state of enterprise software and the challenges ahead.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

NetSuite provides financial software for all your business needs. More than 38,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

@thejoefloyd (Joseph Floyd)

—

TIMESTAMPS:(00:00) Preview and Intro(02:36) Sponsor - NetSuite | Maxio(04:55) Benchmarking Report Background(05:56) Incorporating AI Versus Making Money Off It(09:23) Investing in R&D for AI and How This Affects P&L(11:12) The Real Speed of the Evolution of AI(13:46) The Lasting Power of the Current AI Leaders(15:29) Sponsor - Leapfin | Planful | Mercury(18:53) Growth Versus Profitability and the Rule of 40(20:42) Why the Days of 150% NDR Are Gone(22:53) Why Mid-Stage Companies Are Hardest Hit(24:24) Subscription Based Versus Usage-Based GDR(25:42) Hybrid Pricing Models and AI(27:08) Gross Dollar Retention Rates Versus Net Dollar Retention Rates(27:50) Why Mid-Market Buyers Are Pulling Back(30:37) Impacts on $5 Million - $20 Million ARR Companies(35:04) The Growth Slowdown in $50 Million - $250 Million ARR Companies(37:43) Companies Quietly Shutting Down(40:12) The Effect on Employees(41:02) The Impact of Zombie Companies on the Economy(42:39) The LP-GP Relationship and Returning Capital(44:19) The Denominator Effect(45:27) Public Markets Versus Private Markets(46:26) Why Time Between Early-Stage Rounds Is Lengthening(47:29) Why Some Companies Shouldn’t Raise Venture(50:42) “The Secret Playbook” Refresh

In this episode, CJ interviews Philip Brenckle, CFO of West Shore Home, a company that's revolutionizing the way that people are remodeling their homes. Phil shares insights on the home remodeling market, an unconsolidated industry with a total addressable market (TAM) of $500 billion. He explains how West Shore Home is growing its TAM by meeting customers where they are, before shedding light on the company’s model and its direct-to-consumer component. Phil dives into the role of credit in home remodels and West Shore Home’s financing module. He also breaks down the average split between labor and materials, why the company chooses to work with W2 employees over subcontractors, and how they determine pricing. Additionally, Phil talks about how M&A is part of their strategy, the types of acquisition deals West Shore Home does, and why you should only work with great advisors, before giving tips on how to effectively build relationships with banking partners. 

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 38,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:50) Sponsor - Maxio | Leapfin(05:59) West Shore Home’s TAM(09:07) Growing the TAM(12:52) The D2C Nature of West Shore Home(16:24) Home Remodels and Credit Financing(18:53) Sponsor - Planful | Mercury | NetSuite(21:22) How Credit Works at West Shore Home(23:45) The Cost of a Financing Module(28:56) W2 Employees Versus Subcontractors(31:01) The Split Between Labor and Materials(34:31) Determining Pricing(37:31) M&A and Consolidation in the Home Remodeling Industry(42:29) Structures West Shore Home Uses for M&A Deals(45:29) Why You Shouldn’t Cut Corners on Great Advisors(48:58) Tips for Working With Bankers(52:10) Long-Ass Lightning Round: Extreme Ownership(55:08) Finance Software Stack(56:29) Craziest Expense Story(57:55) Closing Statistics on the Home Remodeling TAM

Amanda Whalen, CFO of Klaviyo, joins CJ in this episode for a deep dive into the roadshow, the IPO process, and ringing that bell. Amanda reflects on the company’s bold decision to go public last year, despite a challenging macroeconomic environment. She shares the factors that guided the management team's timing, the valuation criteria they used to determine the offering price, and how they prepared for it. Amanda provides insight into the IPO journey, discussing everything from choosing a banker to prepping for earnings calls and building the book for investors. The conversation also explores the evolving CFO role and what Amanda means by the term "CFO plus”. She offers valuable insights on what distinguishes great CFOs from good ones, along with tips for recruiting and developing top talent. Tune in to find out why good CFOs are like dolphins, why you should look at your career like a bingo card, and hear other practical advice and entertaining anecdotes. 

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today.

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 38,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(02:07) Sponsor - Leapfin | Planful(04:28) The Right Time for a Business to Go Public(09:55) Reasons to Go Public(12:01) Preparing to Go Public(14:41) Earnings Calls(17:54) Sponsor - Mercury | NetSuite | Maxio(20:44) Evaluating the Initial Offering Price(23:47) Deciding Factors When Choosing a Banker(27:33) Advisors You Work With During an IPO(29:57) How Dual Voting Shares Work(31:26) Building the Book for Investors(33:26) What to Expect From a Roadshow(35:44) The CFO Plus Role(38:00) The Qualities of Good CFOs(39:24) Recruiting and Developing Talent(42:47) Recommended Career Detours and Specialties(46:39) Long-Ass Lightning Round: Big Mistakes and Advice(49:25) Finance Software Stack

After requests for another pricing episode, CJ sits down with returning guest Jason Kap, the founder and CEO of Blue Rocket, a long-tenured Microsoft leader, and an expert in pricing and packaging. Together, they take a deep dive into the evolution of software pricing, tracing its journey from the early days of buying hardware and software together to buying software separately, and all the way through the eras to the emergence of SaaS and today’s usage-based and hybrid models. Jason provides a detailed look at the shifts in the industry, including the rise of application service providers and outsourced infrastructure. As they discuss the current landscape, they highlight the importance of transparency and value abstraction. Then they look to the future with advice on how CFOs can navigate pricing in the new era of AI. Packed with practical insights, this episode offers a comprehensive guide for anyone looking to understand the past, present, and future of software pricing and packaging.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

—

SPONSORS:

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 38,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro(02:26) Sponsor - Planful | Mercury(04:51) Hardware and Software Sold Together(08:11) Software Sold for Hardware(11:48) The Origins of the Enterprise Agreement(15:44) Sponsor - NetSuite | Maxio | Leapfin(18:42) Application Service Providers(23:00) The Evolution of AWS, Google, and Salesforce(27:06) Outsourced Infrastructure and SaaS(33:54) Adobe as the Prime Example of Moving to SaaS(36:32) The Financial Implications of Transitioning to SaaS(38:46) Shelfware in the Next Wave(41:01) Usage-based Pricing(44:25) The Hybrid Model(48:29) Tips for Billing and Overages(52:14) Predictions for the Next Wave: How to Price AI(54:18) Wrap

In this episode, CJ talks with Kingsley Afemikhe, CFO of Shield AI, a company pioneering the future of autonomous jets. Together, they dive deep into the defense tech industry, exploring the critical differences between autonomous vehicles and flight technology, and how innovative private tech companies like Shield AI are driving advancements in the sector. Kingsley provides an insider’s look into Shield AI’s business model, its customer base, and the intricate challenges of managing a hardware/software interface business in such a high-stakes field. He also shares his extensive experience in international deal-making, offering valuable insights into the art of navigating cultural complexities during negotiations and the importance of building a personal board of directors. The discussion wraps up with forward-looking thoughts on how AI could revolutionize careers, bringing a new wave of change to the industry and beyond. Tune in to hear Kingsley’s expert insights on the future of defense technology and its broader impacts.If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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SPONSORS:

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

NetSuite provides financial software for all your business needs. More than 38,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro(02:39) Sponsor - Mercury | NetSuite(06:00) The Autonomous Vehicle Versus Autonomous Flying Market(08:13) Innovation in the Defense Industry(11:00) Who Is Buying Shield AI Products(13:47) Building a Career in Defense(16:04) How Shield AI Makes Money(17:54) Sponsor - Maxio | Leapfin | Planful(20:59) Putting Together Government Proposals(23:44) Managing Working Capital and Debt(26:25) The OODA Loop: Observe, Orient, Decide, Act(27:31) Other Key Leaders in the Defense Industry(28:31) Cross-Cultural Deal-Making(34:53) Raising More Money Versus Less(36:22) Selecting a Personal Board of Directors(39:11) Career Building and Volatility(40:29) AI Optimism and AI FOMO(44:09) Long-Ass Lightning Round: Insurance Mistakes(46:55) Finance Software Stack(48:31) Craziest Expense Story

In this bucket list interview, CJ speaks with Larry Roseman, the CFO of Thumbtack, who shares his deep understanding of running marketplace businesses at scale. They explore Thumbtack's business model and monetization strategy, discussing the customer acquisition cost for both service providers and homeowners. Larry explains why going broad rather than niche can be fundamental for marketplace success, offering a counterintuitive view to that of many marketplace experts. He also talks about the flywheels Thumbtack has developed over time and the company’s shift towards becoming a proactive operating system for homes instead of a reactive marketplace. Additionally, Larry offers valuable insights on value creation from a CFO's perspective, emphasizing the importance of making NPV-positive decisions and the strategic role of the CFO in guiding big business decisions. Hear about the crises that Larry has seen in his career and his advice to “never waste a good crisis”.

If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

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SPONSORS:

NetSuite provides financial software for all your business needs. More than 37,000 thousand 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 ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. 

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. 

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.

Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro(02:31) Sponsor – NetSuite | Maxio(06:13) How Thumbtack Makes Money(09:30) Being Broad as the Key to Marketplace Success(12:31) Charging for the LTV(13:45) The Evolution of the Marketplace Industry(16:21) Sponsor – Leapfin | Planful | Mercury(19:40) Thumbtack’s Two North Stars(21:31) CAC and LTV: Supplier versus Household(23:59) Flywheels versus Network Effects(25:52) Thumbtack’s Evolution: Reactive to Proactive(29:09) Thumbtack’s North Star Metric(32:34) Making the Right NPV Positive Decision(36:43) Helping the C-suite Size Up Big Bets(39:20) Learnings from Crises(40:44) Share-Based Compensation(45:37) Long-Ass Lightning Round: CAC Framework Regrets(50:33) Finance Software Stack(51:53) Craziest Expense Story