Payments Strategy Show

At Rainforest, we answer hundreds of payments questions everyday. What's an ideal take rate for a healthcare platform with $200M in annual volume? Is 75% a good attach rate? What's a realistic goal for adoption? The reality is that most vertical SaaS platforms have no idea how their embedded payments performance compares to the industry.  That’s exactly why we built the 2026 Vertical Saa...

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, construction, transportation, plumbing — understanding fleet payments is critical to building differentiated embedded fintech products.  In this episode, Coast Founder and CEO, Daniel Simon joined host Jo...

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 change management, cultural alignment, and cross-functional enablement.  In this episode, EverHealth ’s Head of Payments, Savannah Krieg joined host Becky Kopplin , VP Payments at Rainforest to share le...

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 operational reality is far more complex than most software platforms expect, particularly when it comes to payments infrastructure, compliance requirements, and regulations.  In this episode, Pamela D...

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 processing the cards; it's navigating the complex compliance requirements around eligibility, letters of medical necessity, and TPA administrator rules.  In this episode, Truemed’s Head of...

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 expanding to lending, banking, and other fintech products. The challenge is knowing what to build next, how to sequence products, and how to drive adoption without massive investment. In this episode, U...

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 math actually makes sense to take on more of it. In this episode, Dogpack’s Chief Revenue Officer, Zaiaad Khan joined host Aaron Steinberg , VP of Revenue at Rainforest, to discuss his extensive ex...

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 launch an exciting new embedded payments integration that helps vertical software platforms capture more payments volume and leave offline methods like checks and cash behind. PayPal Senior Vice Presi...

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 to avoid costly compliance missteps and ensure long-term flexibility as your business scales. Payments attorneys Edward Marshall and Theresa Kananen joined host Joshua Silver , Founder and CEO of...

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 he founded self-storage platform Cubby – he looked before he jumped. The result? A company built on deep market research that treats payments as a core necessity and goes beyond addressing just the sym...

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 optimization of product, pricing, messaging, cost, and more.  On this episode,  Freshbooks VP & General Manager of Payments Shirley Hsu joins host Becky Kopplin to share her experience growing the...

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 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 of magnitude larger than the platform’s payments...

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 and SaaS-powered payments on the rise, software companies are supporting merchants in multiple states or jurisdictions and those merchants can be serving a wide variety of customers across multiple r...

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 episode, Preczn cofounders Malik Velani and Jason Key share how vertical SaaS platforms can take control of their merchant, customer, and payment data to accelerate payment migrations, increase attac...

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 Jacob Olins joined host Becky Kopplin to discuss the unique opportunity for vertical SaaS companies to disrupt traditional banking, the most common challenges, and how to unlock fintech growth. They...

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 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 embe...

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 reve...

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 a...

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 (a...

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 f...

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...

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 A...

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...

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 promis...