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 i ...
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Payments law and how to stay on the right side of it with Edward Marshall and Theresa Kananen
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29:36Payments 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 to the revenue the platform earned. A legal misstep or regulatory violation can risk the entire amount processed plus fines – a total that can be orders…
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Surcharging at scale: rules, risks, and requirements for vertical SaaS platforms with Emily Tsitrian
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26:32Your 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 and SaaS-powered payments on the rise, software companies are supporting merchants in multiple states or jurisdictions and those merchants can be ser…
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Fintech data is the next competitive moat with Malik Velani and Jason Key
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27:56Vertical 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 episode, Preczn cofounders Malik Velani and Jason Key share how vertical SaaS platforms can take control of their merchant, customer, and payment dat…
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The fintech opportunity 99% of vertical SaaS companies aren’t thinking about with Jacob Olins
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31:01Embedded 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 Jacob Olins joined host Becky Kopplin to discuss the unique opportunity for vertical SaaS companies to disrupt traditional banking, the most common chall…
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How payments strategy and execution drive software company valuations with Peter Michaud
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39:30As 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 joins host Brooke Smith to share his exact framework for evaluating a software company’s payments business, how each variable impacts valuation, and h…
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Three keys to Mindbody’s embedded payments success with Brad Greene
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22:41Mindbody 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 COO at H3 Partners and former payments leader at Mindbody and HubSpot) joined host Joshua Silver to discuss the rise of embedded payments and how ve…
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Drive payments revenue by aligning people, profit, and product with Ashley Willson
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30:36When 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 opportunity is driving greater adoption and payments volume. Ashley Willson, co-founder of advisory firm Revolv, joined host Becky Kopplin to share how ver…
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Growing from $2B to $10B annual payment volume with Evan DaSilva
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25:10Evan 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 donor management and fundraising platform Bloomerang. He joined host Joshua Silver to share his experience as a repeat Head of Payments. They discusse…
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How to surcharge the right way (and when to surcharge at all) with Becky Kopplin
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16:14The 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 this episode, Rainforest VP of Payments Becky Kopplin joins host Joshua Silver to share their insights on both questions. They discussed when to conside…
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Operations will make or break your payments product with Emi Keshler and Kyle Scott
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35:38When 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 Emi Keshler and Kyle Scott joined us this week to share their experiences supporting day-to-day operations for embedded payments at vertical software …
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Protect your business from first-party fraud with Shanthi Shanmugam
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27:51The 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 C…
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Grow payments volume and revenue by upgrading your ACH experience with Joshua Silver
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23:07The 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…
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Swallow the frog and become the system of record with Luke Sophinos
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29:19Will 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 value…
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How embedded payments growth can drive 135% net revenue retention with Kevin Lee
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28:43What 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 appr…
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User experience eats everything (including low cost competitors) with Bob Butler
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24:25How 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 differen…
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How robust quoting and invoicing features helped ProLine drive payments adoption with AJ Briley
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18:05One 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 th…
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Agentic commerce with Colin Luce and Joshua Silver
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15:24Basis 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 mor…
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The future of payments will be tokenized (and what it means for software companies) with Colin Luce
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29:00In 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 da…
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Questions every software company should answer before investing in payments with Andrew Mosawi
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24:11Payments 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. The…
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Build a winning payments product by solving your customers' most painful problem with Matthew Goldman
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35:16How 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:…
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The fight against fraud starts with mindset (not technology) with Dwayne Gefferie
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32:34Fraudsters 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 epis…
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How vertical SaaS platforms are reducing embedded payments cost by 30 bps (or more!) with Max Jewell
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24:57The 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 l…
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How modern vSaaS companies are eating incumbents for lunch with Ari Myers
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21:06Vertical 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 st…
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3 secrets to a successful merchant migration with Becky Kopplin
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22:51Merchant 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 …
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Increase payments adoption and reduce churn by optimizing for user experience with Joseph Solomon
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25:09As 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 impa…
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Managing complexity and risk to create a successful payments strategy with Nikita Skitev
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30:06With 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 paymen…
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Instant onboarding, long-tail payment methods, and other shiny objects to avoid with Joshua Silver
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23:55One 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 h…
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Why 85% of SaaS payment offerings underperform -- and how to get it right with Brian Abernethy
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24:52With 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 Spec…
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Matt Brown's journey from SaaS operator to VC and the rise of embedded financial products in SaaS
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25:32Why 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 investo…
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Maximizing revenue at the intersection of SaaS and payments with Ali Mast
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24:03How 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 …
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Tony Caudill's lessons from two vertical SaaS companies and an acquisition
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27:40Tony Caudill shares insights from building a church membership engagement app and an all-in-one financial management platform for youth sports clubs, emphasizing how to choose the right payments provider, create a winning merchant experience, and drive adoption. How integrated payments helped Tony's first SaaS business get acquired Four different a…
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