Essential Questions for Entering the Payments Market

If you’re thinking about adding payments to your software company’s tech stack, listen to this first. Today’s guest knows that turning payments into a prolific growth engine isn’t as simple as plugging in a processor; it’s about knowing when you have the “right to win” and building the infrastructure, team, and go-to-market strategy to make it work. In this episode, Andrew Mosawi of JMI Equity and a self-named “dinosaur in the world of embedded payments”, joins CJ to unpack how embedded payments are reshaping industries, why certain platforms are perfectly positioned to own the payment flow, and when you’re better off staying out of the game. They share the frameworks for sizing the TAM, deciding which vertical plays make sense, and forecasting revenue in a world where payments don’t behave like SaaS, while also referencing real-world use cases. The conversation covers the common mistakes companies make when entering payments, standout examples of companies that have done this well, and the right and wrong questions you should be asking before starting out.

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LINKS:

Andrew Mosawi on LinkedIn: https://www.linkedin.com/in/andrewmosawi/

JMI Equity:

https://www.jmi.com/

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

Mostly metrics:

Companies mentioned:

Mindbody:

https://www.mindbodyonline.com

Blackbaud:

https://www.blackbaud.com

Toast:

https://pos.toasttab.com

Shopify:

https://www.shopify.com

Flagship Advisory Partners:

https://insights.flagshipadvisorypartners.com

BCG “Fortune Favors the Bold: Global Payments Report 2024”: https://www.bcg.com/publications/2024/fortune-favors-bold-global-payments-report

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TIMESTAMPS:

(00:00) Preview and Intro

(02:17) Sponsor – Aleph | RightRev | Navan

(06:50) How the Payments Ecosystem Has Changed in the Last Two Decades

(09:02) The Inflection Point That Brought Payments Into the Mainstream

(10:23) The Size of the Payments Pie in 2025

(11:49) Why Not Every Company Should Do Payments

(14:23) What Makes a Company Well-Positioned To Offer Payments

(15:50) Sponsor – Rillet | Pulley | Brex

(19:42) Having a Strategic High Ground To Offer Payments

(21:35) The Stickiness of Embedded Payments

(24:14) What “Embedded Payments” Means

(27:12) Different Models Used for Embedded Payments

(32:14) A Typical Take Rate for Embedded Payments

(36:45) The Accretive Nature of Embedded Payments and Other Benefits

(40:14) The Next Phase of Payments: Other Finance Solutions

(44:56) CJ’s Mental Model for Assessing Payments at PartsTech

(47:45) Running a Payments Function Versus a Traditional Software Function

(50:46) Sales Dynamics: Traditional SaaS Versus Payments

(52:01) Companies That Have Done Embedded Payments Well

(53:05) The Right and Wrong First Questions To Ask Before Starting in Payments

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#EmbeddedPayments #payments #PaymentsInfrastructure #PayFac #PaymentsStrategy

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