Payments Strategy Show
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!
Episodes
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, accounts for more than 75% of chargebacks, and costs US businesses more than $100B per year.
Shanthi Shanmugam, CEO of dispute automation platform Casap, joined guest-host Brooke Smith to discuss how payment providers, ISVs, and merchan...
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 afterthought.
On this episode, Rainforest Founder and CEO Joshua Silver joins guest host Brooke Smith to discuss how software companies can drive more payments volume and revenue with ACH.
They covered:
- Why ACH is still the backbone of U.S. mo...
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 Sophinos joined Rainforest VP of Revenue Aaron Steinberg to discuss the future of vertical SaaS.
They covered:
- Why focusing on just one or two core values can help software companies build a strong team
- Luke’s proven playbook for su...
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 includes multiple successful exits. He joins host Joshua Silver to discuss the the rise of embedded fintech, how the strongest SaaS companies are approaching embedded payments, and why the most promising SaaS companies are selling all-i...
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 vertical software companies become the system of record with robust vertical workflows and embedded fintech.
They covered:
- One thing Bob would do differently if he was building a payments company all over again
- Contract terms to align ince...
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 problem.
Customers asked for payments. And, when ProLine launched their embedded payments, customers eagerly moved their payments volume to the platform.
On this episode, ProLine Co-Founder and CEO AJ Briley joined host Joshua Silver to share...
Basis Theory Co-Founder and CEO Colin Luce joins Rainforest Founder and CEO Joshua Silver to discuss the future of agentic commerce.
They covered:
- Shopping in an AI-enabled ecosystem vs true agentic commerce
- How certain categories of shopping are likely to adopt AI
- Will agentic commerce drive more shopping (and payments volume) or make shopping more efficient?
- Data and infrastructure needed to power agentic commerce
- Risk management i...
In this episode, Basis Theory Co-Founder and CEO Colin Luce joins Rainforest Founder and CEO Joshua Silver for a deep dive on payments orchestration, tokenization, and vaulting.
They discussed:
- The number one reason to invest in payment orchestration (hint: it's not least-cost routing)
- How software companies can protect their merchant onboarding data and get more control over their payment processing
- The sneaky retention tacti...
Payments pundits tend to say things like “every software company will be a payments company”... but how should software companies really evaluate the payments opportunity?
Andrew Mosawi has helped hundreds of software companies set up and scale their payments businesses, and on this episode he joins host Joshua Silver to share his key insights.
They covered:
- When to bring in a dedicated payments leader (hint: it’s not a certain AR...
How do you build and launch an embedded payments product that delights your customers, boosts retention, and grows your core business? The answer might surprise you.
Product and strategy consultant Matthew Goldman of Totavi joins host Becky Kopplin to share product strategy for software companies adding or optimizing embedded fintech.
They explore:
- 3 essential questions SaaS leaders need to ask before getting started with payments
- ...
Fraudsters are evolving fast. How can software platforms and payments providers stay ahead?
On the latest episode of The Payments Strategy Show, Dwayne Gefferie and Joshua Silver discussed the answers to this question and many more.
Dwayne is known for his contrarian perspectives and deep expertise in payments data and risk management, so this episode goes into the weeds on auth rates, risk management, payments orchestration, and the...
The biggest opportunity for SaaS companies to reduce embedded payments cost usually isn’t negotiating a lower fee with the payment provider.
It’s optimizing interchange.
In this episode, payments supply chain expert Max Jewell explains how interchange fees are determined, where SaaS companies might be able to qualify for better rates, and what to look for in your processing statements to uncover potential savings.
Max shares:
- The...
Vertical SaaS is bifurcating into two distinct approaches – and one approach will dominate.
Joshua Silver (Founder & CEO of Rainforest) is joined by Ari Myers, Head of Commercial Strategy at Kanmon, to talk about the synergy between embedded payments and embedded lending, why the next generation of SaaS platforms will need to be fintech-first to stay competitive, and how to avoid the most common fintech fails.
They covered:
- Tw...
Merchant migrations can be a significant barrier for SaaS companies changing payment providers -- especially if there's concern about merchant pushback or churn.
Wouldn’t it be great if we could get advice from someone who has led dozens of successful migrations impacting many thousands of merchants?
This person is Becky Kopplin (VP of Payments at Rainforest). In this episode of the Payments Strategy Show, sh...
As customers, why do we enjoy interacting with some software and dread others? And how can SaaS companies create that feeling of joy in an embedded payments product?
Payments UX expert Joseph Solomon of WDIR joins us on the Payments Strategy Show to answer these questions and more. We covered:
- One critical UX touchpoint with a disproportionate impact on payments adoption (SaaS companies don’t want to miss this)
- How to bo...
With payments technology getting more and more complicated -- and fraud evolving at a similar rate -- how can SaaS companies build a winning payments strategy in a rapidly changing payments industry?
Nikita Skitev of Payments Strategist joins host Joshua Silver to discuss this question and much more. They covered:
- The best way to learn about payments and fintech quickly when you’re just starting out
- Hidden costs of an al...
One of the biggest mistakes for vertical SaaS companies when it comes to payments is taking on too much.
Too much risk and compliance responsibility, too much technical complexity, or too many features that add more confusion than value.
In this episode, Becky Kopplin interviews Joshua Silver about exactly what SaaS companies must prioritize in a high-value embedded payments offering... and which shiny objects just cause problems.
T...
With so many SaaS companies embracing payments, why do only 10-15% achieve the expected financial results? Brian Abernethy of Utopaya joins host Joshua Silver on this episode to examine what separates the winners from the rest of the pack.
They explore:
- One huge mistake SaaS companies make when choosing a payments provider, and how to avoid it
- Specific contract terms to demand, and terms to reject, when negotiating with...
Why are some SaaS companies able to generate more than half of their revenue from payments, while others struggle to get customers to use the payments feature? Matt Brown of Matrix Partners shares his lessons learned from building fintech into the vertical SaaS platform at Bonsai and working closely with top SaaS and fintech leaders as a VC investor. He covers:
- Why payments should be the first embedded fintech product for almost...
How do software companies transform payments from a bolt-on feature to a thriving profit center? In today's episode of The Payments Strategy Show, Ali Mast of Parachute Advisory shares her experience from a career at the intersection of SaaS and payments, and what she learned from embedding payments in 40+ software platforms.
- Why SaaS and payments companies often "speak different languages" and how to bridge the g...
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