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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
Fleet payments and embedded fintech done right with Coast’s CEO Daniel Simon
Fleet payments represent over 10% of total US B2B card spend, yet most fintech companies have overlooked this massive opportunity. For vertical SaaS platforms serving the physical economy: HVAC,…
From payments infrastructure to platform payments with Savannah Krieg
Building embedded payments from the infrastructure side is one thing, but leading payments at a vertical SaaS platform is entirely different. The challenges shift from technology and compliance to…
What vSaaS leaders should know before expanding to Canada with Pamela Draper
For US-based vertical SaaS platforms, expanding into Canada can seem straightforward at the start. It’s English-speaking, geographically close, and a natural first international market. However, the…
Unlocking HSA/FSA payments for vertical SaaS with Truemed’s Chris Shaw
HSA and FSA cards represent $150 billion in consumer funds today, yet many vertical SaaS platforms serving healthcare, wellness, and fitness aren't set up to accept them. The challenge isn't just…
What comes after payments: Embedded fintech with Unit's Itai Damti
Most vertical SaaS platforms start with embedded payments, and sometimes also end there. However, once the payments offering is live, scaled, and optimized, platforms can grow revenue even more by…
The PayFac Path: Hard-Won Payments Lessons with Zaiaad Khan
Building an embedded payments strategy that actually works requires more than just enabling checkout. It demands a clear view of what you're building, who owns the compliance and risk, and when the…
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…
Frequently Asked Questions
Payments Strategy Show has published 41 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 27m.
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