Payments Strategy Show

Rainforest
  • 5.0 (16)
  • MANAGEMENT
  • UPDATED WEEKLY

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!

  1. FEB 4

    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 legallyExactly what to look out for when switching providers and navigating exclusivity causesWhy 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

    30 min

  2. JAN 20

    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 depthThe 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 softwareWhy 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

    40 min

  3. JAN 6

    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 nowHow to position automation and efficiency as growth levers for SMBsWhy switching to IC+ pricing doesn’t guarantee more marginPricing, product, and cost optimization strategies to maximize payments marginWhen 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

    30 min

  4. 12/16/2025

    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 directlyOne dangerous assumption software companies should never make about paymentsWho actually owns your merchant and transaction data if the contract doesn’t specifyWhy states are setting the rules on pricing, subscriptions, and cancellationsAn 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

    30 min

  5. 12/02/2025

    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-complianceWho bears ultimate responsibility for surcharging compliance, and what platforms need to know before they enable it for their merchantsHow digital wallets make surcharging compliance even more difficultThe danger of treating “convenience fees” as a loophole, and why we’re likely to see increased scrutiny of convenience fees in the near futureSpecific 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

    27 min

  6. 11/18/2025

    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 dataWhy merchant onboarding is the biggest barrier to payment adoption and efficient migrationsHow software companies can increase payments and fintech attach rates with pre-filled onboarding applicationsTwo factors vSaaS leaders must consider when evaluating embedded fintech opportunitiesHow 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

    28 min

  7. 10/28/2025

    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 financeOne leadership decision that separates the embedded fintech winners from everyone elseWhere in the payments journey most software companies get stuck – and how to unlock next level growthHow 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 organizationListen 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

    31 min

  8. 10/14/2025

    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 marketThree critical payments contract terms to know and how they impact valuationWhy software companies should own the merchant relationship including sales, support, and pricingKey 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

    40 min
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5
out of 5
16 Ratings

About

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!

Information

  • Creator
    Rainforest
  • Years Active
    2025 - 2026
  • Episodes
    34
  • Rating
    Clean
  • Copyright
    © 2026 Rainforest Pay, Inc.
  • Show Website
    Payments Strategy Show