Run the Numbers

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.

—

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.

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FOLLOW US ON X:

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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

In this episode, CJ sits down with Eric Newcomer, who runs “Newcomer," or newcomer.co, the largest independent media outlet focused on venture capital. They delve into the art of crafting fundraising announcements, particularly from the CFO’s angle when pitching a company’s raise to the media. The conversation explores the unique appeal of venture capitalists as a subject matter and some of the big stories and personalities that Eric has featured. The discussion also covers the fascinating trend of media companies morphing into VCs, VCs morphing into media companies, and the reasons behind this. Eric sheds light on how a good fundraising announcement should work, how this relates to a company's efforts to attract talent, and how and why to build relationships with the media when not fundraising. Drawing from Eric’s vast industry experience, hear his perspectives on what makes a story compelling and shareable, lessons from his own media business, and his insights on all things venture capital. 

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 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. 

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FOLLOW US ON X:

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@EricNewcomer (Eric Newcomer) 

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TIMESTAMPS:

(00:00) Preview and Intro(02:03) Sponsor – Maxio | Leapfin(05:37) What Makes Venture Capitalists So Intriguing to Cover(08:06) Big Stories and Personalities Covered on Newcomer(11:21) a16z’s Moves into the Media Space(12:37) Conflicts of Interest in the Media Space(14:45) The Convergence of Media and Investing(16:56) Sponsor – Planful | Mercury | NetSuite(21:35) How Eric Gets Tips and Scoops(23:07) How a Good Fundraising Announcement Should Work(26:17) Fundraising Announcements and Attracting Talent(29:33) “Off the Record” Relationships with the Media(36:05) Eric’s Database of Investor Profiles and the Value of Lists(42:12) Differentiated Competitive Moats for Companies versus VCs(43:31) Eric’s Decision to Monetize via Subscriptions(49:42) Regrets from the First Year of Eric’s Business(51:30) Building Newcomer’s Subscriber Base(52:25) The Next Big Thing versus Evergreen Content(56:15) Whether VC Is Bigger or Smaller Than Eric Expected(58:50) Wrap

In this episode, CJ interviews Bryan Morris, CFO of Demandbase, for an in-depth discussion on the complexities of OKRs (Objectives and Key Results). As the planning season for 2025 kicks into gear, Bryan shares his insights on setting the right OKRs, aligning them across departments, and explaining why they often lose momentum. He discusses his approach to tracking OKRs, the tools he uses, and his thoughts on making midyear adjustments. Bryan also talks about the value of weekly written executive team updates and formats for efficient meetings. Bryan, a strong advocate of personality tests, unpacks how they enhance talent management, before shedding light on the tough side of leadership and how to approach moving people out of the company when it’s not working. The episode wraps up with Bryan’s insights on a CFO’s decision-making power over an organization’s software stack, including the risks of tool consolidation and the hidden costs of poor tech choices.

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 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.

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FOLLOW US ON X:

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TIMESTAMPS:(00:00) Preview and Intro(02:34) Sponsor - Leapfin | Planful(05:04) OKRs in Planning Season(07:55) Department OKRs Versus Company OKRs(10:04) The Pros and Cons Stretch Goals(12:19) When and Where Do OKRs Fail(16:28) Sponsor - Mercury | NetSuite | Maxio(19:52) Adjusting OKRs During the Year(21:50) Tools to Track OKRs(22:41) How Weekly Written Team Updates Work(24:53) Formats for Executive Team Meetings(28:20) Talent Management and the Benefits of Personality Tests(32:49) Soft Skills to Screen for When Hiring(33:45) Advice for Off-boarding People(37:25) CFOs and Company-wide Software Decisions(41:59) The Pros and Cons of Tool Consolidation(44:21) Hidden Costs of Choosing the Wrong Technology(45:40) Tips for Negotiating Software Deals(47:30) Long-ass Lightning Round: Wire Fraud Regrets(49:15) Advice to Bryan’s Younger Self(51:58) Finance Software Stack(52:36) Craziest Expense Story

In this mailbag edition, CJ introduces listeners to Run the Numbers’ first intern. Intern Charlie fills us in on what his internship entails and the nature of the early recruitment process for college internships these days. Then CJ answers questions submitted by listeners. He shares his thoughts on when to join a startup to maximize your equity outcome, where to pull cash from when you need to free up budget, what experience he believes is required to run a $100 million+ SaaS company, whether or not you have to sell to the enterprise to become a public SaaS company, and what he means when he says that the gross profit is where the race starts. CJ talks about his own career path, why he switched from consulting and private equity to operator and CFO, and what he wishes he had known about his skills and potential job paths when he was in college. This episode is full of advice and insights for college students and finance professionals alike.

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 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.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:(00:00) Preview and Intro(02:32) Sponsor - Planful | Mercury(04:17) Intern Charlie’s Role at Run the Numbers(07:42) When to Join a Startup to Maximize Your Equity Outcome(12:13) Equity at Different Stages of a Company(13:57) Where to Pull Cash From When You Need to Free Up Budget(15:22) Sponsor - NetSuite | Maxio | Leapfin(18:57) Path to Become CFO of a $100 million+ SaaS Company(21:36) Finding “Personal Product Market Fit”(26:53) Selling to the Enterprise to Become a Public SaaS Company(28:15) The Gross Profit is Where the Race Starts(29:47) The Cost of Goods Sold for SaaS Versus Physical Products(31:02) CJ’s Favorite Writers(32:40) What CJ Would Ask a Candidate in an Interview Process but Can’t(36:10) Common Threads in the “Advice to Younger Self” Question(38:04) CJ’s Advice to College Graduates and Junior Year Students

Having listened to a number of Couchbase’s earning calls, the company’s CFO Greg Henry sits down with CJ to answer some in-depth questions, starting with the rationale behind Couchbase's non-standard fiscal year and the advantages of it. He then delves into his experience of transforming a traditional enterprise subscription model into a managed service consumption business. The conversation covers Couchbase's focus on Annual Recurring Revenue (ARR) as their North Star metric and the art and science of multi-year deals. They discuss how best to interact with sell-side analysts, how callbacks after earnings calls work, and how to manage relationships on the buy side. Greg also reflects on his time at General Electric during its heyday, offering insights into the culture and frameworks that shaped his approach to business today before talking about Matt Cain's framework for Couchbase and how it enables function. Tune in to hear all this and the story of how Greg lost $1 million of operating profit.

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 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.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:(00:00) Preview and Intro(03:16) Sponsor - Mercury | NetSuite(05:40) Non-standard Fiscal Years(09:00) Transitioning From Subscription to Consumption(14:53) Couchbase’s North Star Metric of ARR(16:55) ARR versus RPO and CRPO(18:38) Sponsor - Maxio | Leapfin | Planful(22:14) The Art and Science of Multi-year Deals(24:33) Interacting With Sell-side Analysts(27:28) The “Open Window” After an Earnings Call(31:22) The Benefits of Having Analyst Coverage(32:16) Relationships on the Buy Side(35:44) Working at General Electric During Its Heyday(38:32) Frameworks From Jack Welch(40:52f) Matt Cain’s Framework for Couchbase(42:19) Learnings From GE’s Consent Decree(45:35) Long-ass Lightning Round: How Greg Lost a $1 Million Operating Profit(48:56) Finance Software Stack(50:13) Craziest Expense Story

In this episode, CJ talks to Jessica Lanier, CFO of Restaurant365 and the first CFO guest on the podcast who has firsthand experience as a founder. On top of this, every company she has worked for has been acquired, so she has a wealth of knowledge on all things M&A. She talks about what makes a great CEO-CFO relationship and why a good relationship with the CRO is also so important. She also explores the benefits of operating a company at scale and whether private and public companies require different skills. Jessica shares her most extreme experience of M&A, what finance leaders should expect after their companies are acquired, and the role of trust and credibility in this process. She also discusses her framework for evaluating a company you may want to work for, before offering profound advice on recognizing when you’re ready for your next role. 

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 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

(03:00) Sponsor - NetSuite | Maxio 

(05:44) How Being a Founder Makes You a Better CFO

(10:37) The CFO’s Role in Supporting the CEO

(13:07) The Hallmarks of a Good CFO-CRO Relationship

(17:00) Skills for Private Companies Versus Public Companies 

(20:34) The Benefits of Operating a Company at Scale

(22:52) Sponsor - Leapfin | Planful | Mercury 

(26:28) Important Qualities for Operating at Scale

(27:57) Re-interviewing for a Job After Being Acquired

(31:22) Jessica’s Most Extreme Experience of M&A

(34:45) Fairness, Trust, and Credibility in M&A

(39:07) What a CFO Should Expect After Their Company is Acquired

(43:22) Jessica’s Framework for Evaluating a Company

(50:08) How You Know You’re Ready for Your Next Role

(52:59) Long-ass Lightning Round: Hiring Mistakes and Other Advice

(57:02) Finance Software Stack

(58:16) Craziest Expense Story 

In this solo episode, Run the Numbers host CJ Gustafson breaks down all the different ways software businesses make money. He does an overview of the different monetization models including subscription, consumption, hybrid, transaction-based, and advertising models. He then zooms in on subscription contracts and references the piece he wrote “The ‘Planet Fitness’ Era of SaaS is Over” to discuss professional services, examining the differences between product-led growth (PLG) and sales-led growth models. He talks about the three key things that PLG has influenced CFOs to push for when evaluating buying decisions. He also explains why subscription contracts don’t equate to revenue durability and what real durability is in SaaS, also spelling out (literally) the major differences between recurring revenue and reoccurring revenue, and why you may want a blend of both.

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 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. 

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FOLLOW US ON X:

@cjgustafson222 (CJ)

HELPFUL LINKS:

Deep Dive on Usage Based Models with Gladly's CFO Todd Rakow

The "Planet Fitness" Era of SaaS is Over 

BlackRock Managing Director on the Secrets of Durable Companies 

Mostly Multiples

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TIMESTAMPS:

(00:00) Preview and Intro

(03:01) Sponsor - Maxio | Leapfin

(05:43) Monetization Models

(06:11) Subscription Models

(07:24) Consumption Models

(09:10) Hybrid Models

(10:51) Take Rate or Transaction-based Models

(12:35) Advertising Models

(13:39) Sponsor - Planful | Mercury | NetSuite

(16:41) Subscription Contracts: Product-led Growth Versus Sales-led Growth

(18:32) Getting to Value Fast or Before Purchase

(21:22) Flexibility in Amount of Software Purchased 

(23:01) Showing Clear Value on a Regular Basis

(25:19) What is Real Durability in SaaS

(29:01) Recurring Versus Reoccurring Revenue

(33:40) Wrap

Today on the number one podcast for CFOs, CJ talks to Nicolette Turner, CFO of Headspace. Nicolette shares her unconventional journey into her role and how she first came to work for the company during the pandemic while she was seven months pregnant with her first child. She explains why CFOs should use their company’s products and why and how they should talk directly to customers. Nicolette then sheds light on Headspace’s fascinating and complex business model that includes facets of a B2B, B2C, and B2B2C company. She discusses the challenges of forecasting the business, calculating customer acquisition costs and lifetime value, and monetization within this complex framework, as well as the unique working capital and cashflow challenges they face. She also shares hiring wisdom, including when to promote internally versus hiring externally, what she looks for in a resume, and how building a diverse team unlocks value, while also sharing tools for tough conversations with employees.

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 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.

—

FOLLOW US ON X:

@cjgustafson222 (CJ)

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:03) Sponsor - Leapfin | Planful

(04:08) Nicolette’s Unconventional Journey at Headspace

(12:13) Understanding Your Company’s Product

(14:05) Why and How CFOs Should Talk to Customers 

(17:15) Numbers Are One-dimensional 

(19:09) Sponsor - Mercury | NetSuite | Maxio

(22:31) Headspace’s Business Model: B2B, B2C, and B2B2C

(27:01) Forecasting for a Highly Complex Model

(29:35) Calculating Customer Acquisition Costs 

(30:56) The Healthcare Overlap

(33:19) Unique Working Capital and Cashflow Challenges

(37:11) Promoting From Within Versus Hiring

(42:18) Tools for Tough Conversations With Employees

(45:32) Moving From a Big Company to a Small One

(48:40) How Building a Diverse Team Unlocks Value

(53:05) Long-ass Lightning Round: Advice on Learning From Mistakes

(56:31) Finance Software Stack

(57:50) Craziest Expense Story

In this solo episode, CJ does a deep dive into cash conversion cycles, telling listeners what he’s learned about them, sharing real-life tales from his career, and explaining how certain companies are excelling at theirs. CJ starts by breaking down how he got his company’s Days Sales Outstanding (DSO) down from 55 days to 37 days (a 33% improvement) and Days Payable Outstanding (DPO) up from 35 days to 47 days in the course of a year. Then he talks about how he achieved this through three big changes that he made, before delving into inventory management. Listen in to hear the stories of companies who have perfected the art of the cash conversion cycle and the dynamic methods they use to manage their cash inventory, their accounts receivable, and their accounts payable.

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 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.

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.

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.

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FOLLOW US ON X:

@cjgustafson222 (CJ)

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TIMESTAMPS:

(00:00) Preview and Intro

(01:30) Sponsor - Mercury | NetSuite

(03:43) The DSO and DPO Improvements CJ made

(05:16) Changes to the Off-the-shelf Customer Agreement

(06:18) ACH payments

(09:25) Renegotiating Payables

(11:45) A Note on Inventory Management

(12:35) The Innovative Way CJ’s College Professor Delayed Payments

(14:53) Sponsor - Maxio | Planful | Leapfin

(17:58) Gymshark’s Pre-sale Drop Hack

(20:43) Starbucks’s Gift Card Program

(23:34) Chewy Pet Food’s Subscription Model

(26:11) Ferrari’s Customization and Their Cash Conversion Cycle

(27:58) Virgin Airline’s Dynamic Pricing Strategies & Creative Financing

(30:54) Wrap

Simone Nardi, the CFO of Globalization Partners, one of the largest providers of Employer Of Record (EOR) services, joins CJ for a masterclass in expanding internationally. Simone explains the concept of an Employer of Record, how it handles employment-related tasks and obligations for companies going abroad, and how it differs from a Professional Employer Organization (PEO). Together they flesh out a framework for CEOs and CFOs looking to build teams internationally. They talk about everything that goes into hiring great people abroad and doing it in a cost-efficient and strategic manner, including how to budget for an international workforce, staying abreast of changing regulations, using EORs to move employees between countries, considering the fluctuation of currency values, and even exit cost considerations. Simone also sheds light on Globalization Partners’ business model, the different revenue lines that they forecast for, and the metrics they track.

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.

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.

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. 

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)

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:12) Sponsor - NetSuite | Maxio 

(04:47) Definition of Employer Of Record (EOR)

(06:51) Definition of Professional Employer Organization (PEO)

(11:19) Key Considerations for Expanding Globally

(15:16) Use Cases for an EOR 

(16:01) Costs That People Overlook When Hiring Abroad

(19:28) Sponsor - Planful | Leapfin | Mercury

(23:15) Time Considerations for Establishing an International Team

(24:20) Using EORs to Move Employees Between Countries 

(24:54) Staying Abreast of Evolving Regulations 

(26:12) Budgeting for an International Workforce With an EOR Versus Without One

(28:48) Exit Cost Considerations

(30:05) Considering the Effects of Currency Swings

(32:54) Countries Seeing Growth in Outsourcing of Labor

(34:55) The Different Revenue Lines That Globalization Partners Forecasts for

(36:14) The Metrics That the Company Tracks

(38:55) The Technological Component of Globalization Partners

(41:31) Long-ass Lightning Round: Advice on Pace, Reading the Room, and Delegation

(47:37) Craziest Expense Story