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A newsletter for current and aspiring CFOs. SaaS Metrics, Go to Market Strategy, and Capital Market insights (you can actually understand).

cjgustafson.substack.comSource feed ↗13 episodes

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40 Years of IPOs with Jay Ritter: What the Data Actually Says

In this episode of Run the Numbers, CJ sits down with Jay Ritter, the “Mr.

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How AI Is Rewriting Product-Market Fit, Pricing, and Go-to-Market

CJ sits down with Rebecca Schwartz of Tabs, Fred Havemeyer of Fleet AI, and Rahul Rekhi of Rogo for a live conversation about what it actually takes to build an AI-native company.

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The Stripe Guide to Pricing, Billing, and Quote-to-Cash with Wisam Hirzalla

In this episode of Run the Numbers, CJ sits down with Wisam Hirzalla, Head of Product at Stripe Billing, to trace the full journey of a dollar—from product packaging and pricing through quoting, contracts, billing, tax, collections, and revenue recognition.

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The CFO-COO Is Coming: Meredith Finn of Front on the Future of Finance

Front CFO & COO Meredith Finn joins CJ to explain why finance leaders are taking on more of the operator’s job.

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Xero’s CFO: Why Finance Is Taking On More of the Business

In this episode of Run the Numbers, CJ Gustafson sits down with Xero CFO Claire Bramley to discuss how the CFO role is expanding beyond finance into strategy, operations, transformation, and technology.

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A CFO Explains Private Jets

On this episode of Run the Numbers, CJ and Ben trace corporate private jets from Sam Walton’s scrappy two-seater to Alex Karp’s $17 million jet bill.

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The Business of Saving Lives: Inside RapidSOS

On this episode of Run the Numbers, CJ Gustafson sits down with Richard Haram, VP of Finance at RapidSOS, to unpack how finance supports a public safety AI platform that helps 911 operators and first responders act faster.

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Building an AI-Native Finance Team with Plaid CFO Seun Sodipo

On this episode of Run the Numbers, CJ sits down with Plaid CFO Seun Sodipo to unpack how Plaid’s three-layer network powers digital finance and monetizes financial activity.

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The CFO Rule for AI Forecasting: “It’s Not Zero” | Dan Griggs

In this episode of Run the Numbers, CJ sits down with Dan Griggs, CFO of Intercom, to break down how finance leaders should think about pricing, forecasting, and resource allocation in the AI era.

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How finance shows its value beyond being the “no” department | Maria Izurieta

In this episode of Run the Numbers, CJ sits down with Maria Izurieta, CFO of Huntress, to unpack what it really means to lead finance as a connective tissue across the organization.

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How the Best CFOs Lead Without Being the CEO | Ken Stillwell

In this episode of Run the Numbers, CJ sits down with Ken Stillwell, CFO and COO of Pegasystems, to explore the realities of leading from the second seat.

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How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubaker

In this episode of Run the Numbers, CJ sits down with Chris Brubaker, SVP of Finance at Postscript, who’s helped build the finance function from the ground up.

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The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq

In this episode of Run the Numbers, CJ sits down with Bruno Annicq, CFO of Wellhub (formerly Gympass), to unpack a practical finance playbook built around cash discipline, sustainable growth, and simplicity.

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