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
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 joins host Brooke Smith to share his exact framework for evaluating a software company’s payments business, how each variable impacts valuation, and how software companies can close the gap between their current payments business and t...
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 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 vertical SaaS companies can launch a successful embedded payments offering.
They covered:
<...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 opportunity is driving greater adoption and payments volume.
Ashley Willson, co-founder of advisory firm Revolv, joined host Becky Kopplin to share how vertical software companies can grow payments revenue by optimizing their GTM strategy for...
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 donor management and fundraising platform Bloomerang. He joined host Joshua Silver to share his experience as a repeat Head of Payments.
They discussed:
- Why early-stage vertical SaaS founders can’t afford to ignore payments
- Traps to av...
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 this episode, Rainforest VP of Payments Becky Kopplin joins host Joshua Silver to share their insights on both questions. They discussed when to consider surcharging, which problems surcharging does (and does not) solve, and – if you do d...
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 Emi Keshler and Kyle Scott joined us this week to share their experiences supporting day-to-day operations for embedded payments at vertical software companies, and how to transform payments support from cost center to revenue driver.
We...
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...
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