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About This Podcast
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!
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Recent Episodes
Rainforest + PayPal: The future of embedded payments with Taira Hall
For vertical SaaS platforms, offering a trusted and familiar payment experience can be the difference between checkout conversion and cart abandonment.Rainforest and PayPal recently joined forces to…
Payment aggregation and contract pitfalls with Edward Marshall and Theresa Kananen
Payment aggregation models come with complex legal and contractual implications that many vertical SaaS platforms overlook. For those platforms who are evaluating a payments provider, it's critical…
Why market research beats intuition in vertical SaaS with Adam Flemming
Diving into a brand new market without any deep knowledge or industry research is how many kick off their entrepreneurial journeys. After five startups, Adam Flemming took a different approach when…
S1E31 How Freshbooks grew payments margin by 75% in one year with Shirley Hsu
Bolting on payments can be a “quick win” for vertical software companies, but it doesn’t unlock the full opportunity. Experienced payments leaders know the biggest gains are the result of continuous…
S1E30 Payments law and how to stay on the right side of it with Edward Marshall and Theresa Kananen
Payments revenue is advantageous to software platforms because they can earn basis points on every transaction that flows through the platform. But the risk exposure is asymmetric. It’s not limited…
S1E29 Surcharging at scale: rules, risks, and requirements for vertical SaaS platforms with Emily Tsitrian
Your merchants want to surcharge… are you prepared for the compliance risk that comes with it?Surcharging for one business that operates in one state is relatively straightforward. But with ecommerce…
S1E28 Fintech data is the next competitive moat with Malik Velani and Jason Key
Vertical SaaS operators understand the importance of data, but it’s easy to discount merchant onboarding data and payment data because historically those have belonged to the payment provider.On this…
S1E27 The fintech opportunity 99% of vertical SaaS companies aren’t thinking about with Jacob Olins
Embedded fintech is a massive opportunity for vertical software companies, but most SaaS operators aren’t thinking about the full potential.WorkWave SVP & GM of Fintech and Strategic Partnerships…
S1E26 How payments strategy and execution drive software company valuations with Peter Michaud
As Head of Consulting and Market Intelligence at TSG, Peter Michaud is often engaged by Private Equity firms to help value software companies with integrated or embedded payments. In this episode, he…
S1E25 Three keys to Mindbody’s embedded payments success with Brad Greene
Mindbody is admired as an embedded payments role model by SaaS operators and investors alike.How can other vertical SaaS platforms replicate their success?On this episode, Brad Greene (Co-Founder and…
S1E24 Drive payments revenue by aligning people, profit, and product with Ashley Willson
When software companies want to increase payments revenue, payment provider fees are often the first place they look.But cost cutting yields only a very limited margin increase.The real growth…
S1E23 Growing from $2B to $10B annual payment volume with Evan DaSilva
Evan DaSilva grew Buildium’s embedded payments volume from $2B/yr to $10B/yr, contributing to a 446% increase in valuation over just 42 months and a $580M acquisition.Now, Evan is SVP of Payments at…
S1E22 How to surcharge the right way (and when to surcharge at all) with Becky Kopplin
The most frequently asked questions about surcharging tend to focus on surcharging compliance.Compliance is important. But the first question should be “is surcharging even the right solution?” In…
S1E21 Operations will make or break your payments product with Emi Keshler and Kyle Scott
When vertical software companies transition from referral-based payment providers to an embedded solution, one of the critical challenges is bringing payments support in-house.Vertical SaaS veterans…
S1E20 Protect your business from first-party fraud with Shanthi Shanmugam
The chargeback exists to protect consumers. And it assumes that all consumers are good actors. But what happens when they’re not?First party fraud is increasing by 30% every year.It’s hard to detect,…
S1E19 Grow payments volume and revenue by upgrading your ACH experience with Joshua Silver
The Automated Clearing House (ACH) network moved $86 trillion in the U.S. in 2024 – more than 7x the four major card networks combined.Yet the big embedded payment providers treat ACH as an…
S1E18 Swallow the frog and become the system of record with Luke Sophinos
Will AI erode vertical SaaS? How can vertical software companies win market share when enterprise customers can use AI to build their own systems?Vertical software founder, CEO, and investor Luke…
S1E17 How embedded payments growth can drive 135% net revenue retention with Kevin Lee
What does it take to grow a SaaS company from pre-revenue to market leader or scale to a successful exit?Kevin Lee has been a software and payments leader for more than 25 years and his track record…
S1E16 User experience eats everything (including low cost competitors) with Bob Butler
How can a vertical SaaS company become THE operating system for their industry?Fintech board member, investor, and advisor Bob Butler joins Rainforest VP of Payments Becky Kopplin to discuss how…
S1E15 How robust quoting and invoicing features helped ProLine drive payments adoption with AJ Briley
One of the biggest challenges for software companies launching embedded payments is adoption. How do you get customers to use embedded payments?Roofing CRM platform ProLine didn't have this…
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Payments Strategy Show has published 35 episodes since February 2025, covering topics in Business, Management.
Payments Strategy Show is currently highly active with new episodes every 2 weeks. Average episode length is 26m.
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