Payments Strategy Show

Rainforest

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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#44
August 11 · 32 min
Cash flow, ACH & embedded payments in field services with Adam Holden
In field services, cash flow isn't just a metric. It's the driving force of the business. For AV integrators and custom installers, payments can be complex. Large ticket sizes, progress-based billing, recurring service contracts, and a heavy preference for ACH make the payments needs of this vertical unlike almost any other. Getting it right means understanding how your customers run their businesses. And then building payments around that, not around just a generic playbook. In this episode, Adam Holden, Head of Payments at D-Tools, joined host Becky Kopplin, VP Payments at Rainforest to share how D-Tools navigated the unique ACH-heavy payment landscape of field services, and why embedded payments as a core business model, not a feature is vital for customer adoption. They discussed: How offering payments flexibility helped their customer reduce accounts receivable by 70% Why embedding payments as a core part of the product, not a feature is the single biggest driver of customer adoption and stickiness How cross-functional alignment across leadership, sales, product, and support led to two industry award wins within months of launching embedded payments The way embedded payments actually makes support easier, not harder How to use the unique data you already have on your vertical to build a payments strategy no generic platform can replicate The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#43
July 28 · 31 min
Beyond the donation: embedded payments done right for non-profits with Tithe.ly’s Chris Phillips
Embedding payments into a faith-based and mission-driven vertical isn't just a product decision, it's one that’s based around personal values. For vertical SaaS platforms serving nonprofits and churches, payments aren't about commerce. Every single transaction is an act of generosity. That changes everything, from how you design the user experience to how you think about reliability, reporting, and what comes next in your fintech stack. In this episode, Chris Phillips, CFO at Tithe.ly, joined host Becky Kopplin, VP Payments at Rainforest, to share what his career across vertical SaaS, and now Tithe.ly, has taught him about building payments that serve a mission, not just a bottom line. He also shares what building payments for 50,000+ churches actually looks like. They discussed: Why failed transactions in a non-profit vertical hit completely differently than any other How to adapt your payments playbook for a vertical where giving is personal, not transactional Why fund accounting and tax-exempt reporting make church payments uniquely complex How reducing onboarding friction gives churches hours back to focus on their mission Where Tithe.ly's fintech stack is headed next and the north star guiding every decision The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#42
July 14 · 33 min
From MindBody to Jane App: 15 Years of Embedded Payments Lessons with Emily Bartels
Embedding payments successfully isn't just a product decision. It's a cultural one. For vertical SaaS platforms looking to grow revenue through payments, understanding how to build the right culture, hire the right leader, and expand into embedded fintech strategically is the difference between payments that thrive and payments that stall. In this episode, Emily Bartels, VP of Payments at Jane App, joined host Becky Kopplin, VP Payments at Rainforest, to discuss what 15+ years across platforms like MindBody, Skimmer, and Jane App have taught her about embedding payments the right way. That’s everything from back book attachment to building payments into a company’s DNA. They discussed: Why payments culture has to start at the top and what needs to happen before your payments leader's first day on the job How to adapt a payments playbook across verticals without copy-pasting it What it really means to make payments "native", and why it just doesn't work without it The GM mindset every payments leader needs to succeed across product, sales, marketing, and customer success How to think about embedded fintech expansion, what to move fast on and what deserves a deeper strategic bet The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#41
June 16 · 27 min
What the 2026 Embedded Payments Benchmark reveals about vertical SaaS
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 SaaS Embedded Payments Benchmarking Study, so platforms can stop guessing and start benchmarking. In this episode, Joshua Silver, Founder and CEO of Rainforest sits down with Brooke Smith, who led the study, to discuss the key findings on adoption, leadership, take rate optimization, and what the highest-performing platforms are doing differently. They discussed: 📊 The adoption gap: 78% of platforms are targeting an adoption rate of 71% or more but only 25% of platforms are currently performing at that level 👔 Why C-suite payments leaders drive significantly better performance across all metrics 💡 How real-time performance dashboards unlock better decision-making and strategy 💰 The surprising impact of dedicated payments leadership on take rate optimization 🚀 What mature high-performers achieve: 78% median adoption and 35% of total revenue from payments The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#40
June 1 · 30 min
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, 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 Joshua Silver, Founder and CEO of Rainforest to discuss how vertical SaaS platforms can approach embedded fintech products, why simplicity matters more than cash back, and the significance of integrating payments into core workflows rather than just bolting them on. They discussed: What makes fleet payments so unique and the lessons that translate to other vertical specific payment needs How to build differentiated embedded fintech products by deeply understanding your vertical's workflows Why fraud prevention through data and controls is more valuable than reward programs The reason vertical SaaS platforms should partner, not build fintech on their own Why "giving money meaning" by integrating payments into core workflows drives stickiness The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#39
May 20 · 40 min
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 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 lessons from both sides of the payments world, including what surprised her most about switching from infrastructure provider to platform operator, and the critical success factors that actually move the needle. They discussed: Why 90% of platforms should choose embedded payments over becoming a PayFac Why cultural alignment matters more than technology when launching payments The key metrics platforms should track: attachment, activation, TPV, take rate, and more How to think about payments pricing in the context of total contract value, not just take rate The importance of focusing on people and processes over optimizing tools and operations The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#38
May 11 · 23 min
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 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 Draper, President of Digital Commerce Payments joined host Joshua Silver, Founder and CEO of Rainforest to break down everything platforms need to know about building payments in Canada such as navigating different payment rails, the Retail Payment Activities Act and why boots on the ground matter. They discussed: Why Canada requires direct regulatory registration Canada's different payment rails including Interac e-Transfer, EFT, and the Real-Time Rail What the Retail Payment Activities Act (RPAA) means for payment service providers How to navigate the non-negotiable regulatory relationships and compliance requirements Why AI won’t replace payments, and how embedded fintech strengthens SaaS businesses The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#37
April 21 · 31 min
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 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 GTM Partnerships, Chris Shaw joined host Aaron Steinberg, VP Revenue at Rainforest, to break down how HSA/FSA acceptance works, why compliance is the real moat, and how vertical software platforms can unlock this revenue opportunity for their merchants. They discussed: What HSA/FSA accounts are and the massive untapped payments opportunity Why compliance is a big challenge and how the right payments partner makes it seamless How enabling HSA/FSA acceptance increases average order value by 30% The reason consumers are now starting their shopping journeys in HSA/FSA marketplaces Everything platforms need to know about letters of medical necessity and dual eligibility The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#36
April 1 · 33 min
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 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, Unit’s CEO and Co-Founder, Itai Damti joined host Joshua Silver, Founder and CEO at Rainforest to share the embedded fintech playbook for vertical SaaS platforms, including how to maximize revenue, avoid common pitfalls, and leverage the "system of action" strategy for higher adoption. They discussed: How embedded finance has evolved from early adopters to plug-and-play solutions Why your payment processor is not your embedded finance partner The "system of action" strategy that drives higher fintech adoption rates Why cashflow is king and how the right messaging is the key to success with SMBs How software platforms can launch embedded finance without building compliance teams The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#35
March 24 · 41 min
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 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 experience in payments, how he thinks about embedding payments into software platforms, and the hard-won lessons behind choosing the right PayFac model for your business. They discussed: Payments infrastructure is the central nervous system of your business, not an afterthought Why vertical SaaS platforms are falling into significant payments volume without truly understanding their own cost center How to approach the PayFac decision – it isn't triggered by a single milestone, but by a confluence of pressures Key differences between different PayFac models and how to evaluate which makes sense for your business Why transparency about pricing and interchange is still a competitive differentiator in payments The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#34
March 4 · 24 min
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 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 President and Head of SMB Commercial Taira Hall joined host Joshua Silver to discuss the exciting collaboration, how platforms can leverage PayPal's ecosystem and why payments must be treated as a core workflow, not an afterthought. They discussed: Rainforest and PayPal's latest integration for platforms looking to win more volume Why treating payments as an afterthought leads to cart abandonment and lost revenue How Venmo helps service-based businesses acquire new customers through social proof Common mistakes platforms make in their checkout experience and how it impacts processing volume Why platforms need to prepare for AI agents driving customer purchases The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#33
February 4 · 29 min
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 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 Rainforest to clarify payment models, explain compliance obligations, and share strategies for navigating provider contracts. They discussed: What payment aggregations really means (PayFac, merchant of record, marketplace) Why merchant of record status doesn't eliminate compliance responsibilities How the flow of funds differentiates payment models and why it matters legally Exactly what to look out for when switching providers and navigating exclusivity causes Why evaluating a payments provider’s reputation and contractual flexibility matters The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
#32
January 20 · 40 min
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 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 symptoms of customer issues. In this episode, Cubby’s Founder, Adam Flemming joined host Becky Kopplin to share hard-won lessons on building a successful vertical SaaS company the right way. They discussed: Why researching the market before launching a company is critical – don't jump into the pool without knowing the depth The critical reason vertical SaaS leaders must treat payments as a core product feature, not an afterthought How AI’s biggest value is to eliminate generic tasks so operators can focus on what differentiates their business "Simple" businesses like self-storage are more complex than they appear and require sophisticated software Why digging deep to the root cause of customer problems is better than just providing surface-level support The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
S1 · E31
January 6 · 29 min
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 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 business at Freshbooks and the three critical levers to drive meaningful margin expansion. They discussed: The marketing message that’s resonating with service-based business owners to drive payments adoption right now How to position automation and efficiency as growth levers for SMBs Why switching to IC+ pricing doesn’t guarantee more margin Pricing, product, and cost optimization strategies to maximize payments margin When to hire a payments leader and how to align the organization for payments success The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
S1 · E30
Dec 16, 2025 · 29 min
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 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 revenue. To help us navigate the legal and regulatory landscape, payments attorneys Edward Marshall and Theresa Kananen joined host Joshua Silver to explain why payments is so heavily legislated and regulated, common pitfalls, and the best way to navigate challenging situations. They discussed: How software platforms might be held responsible for a merchant’s actions even if they don’t touch the money directly One dangerous assumption software companies should never make about payments Who actually owns your merchant and transaction data if the contract doesn’t specify Why states are setting the rules on pricing, subscriptions, and cancellations An obscure 1989 law that can turn an accurate statement on a merchant application into a legal and financial nightmare The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
S1 · E29
Dec 2, 2025 · 26 min
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 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 regions. And the rules vary. Surcharging is governed by a patchwork of state regulations, card brand rules, industry norms, and customer expectations. On this episode, Yeeld Co-founder and CEO Emily Tsitrian joins Becky Kopplin for a deep dive in surcharging compliance for vertical SaaS platforms. They covered: How governing bodies monitor and enforce surcharging rules, and the devastating costs of non-compliance Who bears ultimate responsibility for surcharging compliance, and what platforms need to know before they enable it for their merchants How digital wallets make surcharging compliance even more difficult The danger of treating “convenience fees” as a loophole, and why we’re likely to see increased scrutiny of convenience fees in the near future Specific verticals and card-mix profiles where surcharging makes sense (and where it doesn’t) The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
S1 · E28
Nov 18, 2025 · 27 min
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 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 attach rates, and grow fintech revenue. They covered: The hidden costs of letting a payment provider own your merchant onboarding and payment data Why merchant onboarding is the biggest barrier to payment adoption and efficient migrations How software companies can increase payments and fintech attach rates with pre-filled onboarding applications Two factors vSaaS leaders must consider when evaluating embedded fintech opportunities How platforms can go beyond data ownership and leverage it to build a sustainable competitive advantage The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
S1 · E27
Oct 28, 2025 · 31 min
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 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 discussed: How Square paved the way for embedded finance One leadership decision that separates the embedded fintech winners from everyone else Where in the payments journey most software companies get stuck – and how to unlock next level growth How to evaluate your embedded fintech opportunities and decide where to start (hint: it’s not always payment acceptance) Two archetypes for a payments leader, and how to choose the right payments leader for your organization Listen to the Acquired podcast episode on Visa that Jacob recommended during the conversation. The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
S1 · E26
Oct 14, 2025 · 39 min
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 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 their future potential. They covered: Why investors care about payments (hint: it’s not just about revenue) The right to win: why it matters, how to evaluate it, and what it says about your addressable market Three critical payments contract terms to know and how they impact valuation Why software companies should own the merchant relationship including sales, support, and pricing Key insights from merchant-level volume and profitability – and why you need this data to make business decisions The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay
S1 · E25
Sep 30, 2025 · 22 min
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 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: The most frequently overlooked contributors to a successful embedded payments launch (don’t ignore these) How Shopify democratized e-commerce and what vSaaS platforms can learn from their success 3 factors that drove Mindbody's payments revenue growth and how companies are replicating their success The most important consideration when choosing your payments provider (hint: it’s not price) How vertical software can still win in the AI era The Payments Strategy Show is brought to you by Vertex and Rainforest. Vertex: The Vertical Software Conference This invite-only event and community offers networking, learning, and unique insights on go-to-market, monetization, product expansion, fundraising, and M&A. Learn more: https://www.vertexconference.com/ Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference Rainforest is the embedded payments purpose-built for vertical SaaS. Grow revenue with the only payfac-as-a-service provider optimized to help you drive more payments volume at higher margins, without risk or compliance headaches. Learn more: https://rainforestpay.com Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay

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