Payments Strategy Show
By Rainforest
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Category: Management
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Episodes: 42
Description
When vertical SaaS platforms hear about the success of companies like Toast or Shopify at monetizing payments, it’s tempting to think they can just integrate payments and double their revenue overnight.
The reality is a bit more complex, and a lot of SaaS companies miss out on the full revenue potential because their payments product, positioning, or pricing is a little off.
Seemingly insignificant details of the payments implementation and go-to-market strategy can have a disproportionate impact on the financial success of a payments offering.
Join host Joshua Silver in conversations with SaaS leaders, investors, and industry experts to illuminate the details that actually move the needle – so you can optimize your payments offering for maximum adoption, revenue, and enterprise value.
New episodes biweekly on Tuesdays!
| Episode | Date |
|---|---|
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What the 2026 Embedded Payments Benchmark reveals about vertical SaaS
|
Jun 16, 2026 |
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Fleet payments and embedded fintech done right with Coast’s CEO Daniel Simon
|
Jun 01, 2026 |
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From payments infrastructure to platform payments with Savannah Krieg
|
May 20, 2026 |
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What vSaaS leaders should know before expanding to Canada with Pamela Draper
|
May 11, 2026 |
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Unlocking HSA/FSA payments for vertical SaaS with Truemed’s Chris Shaw
|
Apr 21, 2026 |
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What comes after payments: Embedded fintech with Unit's Itai Damti
|
Apr 01, 2026 |
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The PayFac Path: Hard-Won Payments Lessons with Zaiaad Khan
|
Mar 24, 2026 |
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Rainforest + PayPal: The future of embedded payments with Taira Hall
|
Mar 04, 2026 |
|
Payment aggregation and contract pitfalls with Edward Marshall and Theresa Kananen
|
Feb 04, 2026 |
|
Why market research beats intuition in vertical SaaS with Adam Flemming
|
Jan 20, 2026 |
|
How Freshbooks grew payments margin by 75% in one year with Shirley Hsu
|
Jan 06, 2026 |
|
Payments law and how to stay on the right side of it with Edward Marshall and Theresa Kananen
|
Dec 16, 2025 |
|
Surcharging at scale: rules, risks, and requirements for vertical SaaS platforms with Emily Tsitrian
|
Dec 02, 2025 |
|
Fintech data is the next competitive moat with Malik Velani and Jason Key
|
Nov 18, 2025 |
|
The fintech opportunity 99% of vertical SaaS companies aren’t thinking about with Jacob Olins
|
Oct 28, 2025 |
|
How payments strategy and execution drive software company valuations with Peter Michaud
|
Oct 14, 2025 |
|
Three keys to Mindbody’s embedded payments success with Brad Greene
|
Sep 30, 2025 |
|
Drive payments revenue by aligning people, profit, and product with Ashley Willson
|
Sep 16, 2025 |
|
Growing from $2B to $10B annual payment volume with Evan DaSilva
|
Aug 19, 2025 |
|
How to surcharge the right way (and when to surcharge at all) with Becky Kopplin
|
Aug 05, 2025 |
|
Operations will make or break your payments product with Emi Keshler and Kyle Scott
|
Jul 24, 2025 |
|
Protect your business from first-party fraud with Shanthi Shanmugam
|
Jul 08, 2025 |
|
Grow payments volume and revenue by upgrading your ACH experience with Joshua Silver
|
Jun 24, 2025 |
|
Swallow the frog and become the system of record with Luke Sophinos
|
Jun 17, 2025 |
|
How embedded payments growth can drive 135% net revenue retention with Kevin Lee
|
Jun 10, 2025 |
|
User experience eats everything (including low cost competitors) with Bob Butler
|
Jun 03, 2025 |
|
How robust quoting and invoicing features helped ProLine drive payments adoption with AJ Briley
|
May 27, 2025 |
|
Agentic commerce with Colin Luce and Joshua Silver
|
May 20, 2025 |
|
The future of payments will be tokenized (and what it means for software companies) with Colin Luce
|
May 13, 2025 |
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Questions every software company should answer before investing in payments with Andrew Mosawi
|
May 06, 2025 |
|
Build a winning payments product by solving your customers' most painful problem with Matthew Goldman
|
Apr 29, 2025 |
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The fight against fraud starts with mindset (not technology) with Dwayne Gefferie
|
Apr 22, 2025 |
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How vertical SaaS platforms are reducing embedded payments cost by 30 bps (or more!) with Max Jewell
|
Apr 15, 2025 |
|
How modern vSaaS companies are eating incumbents for lunch with Ari Myers
|
Apr 08, 2025 |
|
3 secrets to a successful merchant migration with Becky Kopplin
|
Apr 01, 2025 |
|
Increase payments adoption and reduce churn by optimizing for user experience with Joseph Solomon
|
Mar 25, 2025 |
|
Managing complexity and risk to create a successful payments strategy with Nikita Skitev
|
Mar 18, 2025 |
|
Instant onboarding, long-tail payment methods, and other shiny objects to avoid with Joshua Silver
|
Mar 11, 2025 |
|
Why 85% of SaaS payment offerings underperform -- and how to get it right with Brian Abernethy
|
Mar 04, 2025 |
|
Matt Brown's journey from SaaS operator to VC and the rise of embedded financial products in SaaS
|
Feb 25, 2025 |
|
Maximizing revenue at the intersection of SaaS and payments with Ali Mast
|
Feb 18, 2025 |
|
Tony Caudill's lessons from two vertical SaaS companies and an acquisition
|
Feb 11, 2025 |