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. 1D AGO

    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 opportunityWhy compliance is a big challenge and how the right payments partner makes it seamlessHow enabling HSA/FSA acceptance increases average order value by 30%The reason consumers are now starting their shopping journeys in HSA/FSA marketplacesEverything 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

    31 min

  2. APR 1

    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 solutionsWhy your payment processor is not your embedded finance partnerThe "system of action" strategy that drives higher fintech adoption ratesWhy cashflow is king and how the right messaging is the key to success with SMBsHow 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

    34 min

  3. MAR 24

    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 afterthoughtWhy vertical SaaS platforms are falling into significant payments volume without truly understanding their own cost centerHow to approach the PayFac decision – it isn't triggered by a single milestone, but by a confluence of pressuresKey differences between different PayFac models and how to evaluate which makes sense for your businessWhy 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

    41 min

  4. MAR 4

    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 volumeWhy treating payments as an afterthought leads to cart abandonment and lost revenueHow Venmo helps service-based businesses acquire new customers through social proofCommon mistakes platforms make in their checkout experience and how it impacts processing volumeWhy 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

    25 min

  5. 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

  6. 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

  7. 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

  8. 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
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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
    38
  • Rating
    Clean
  • Copyright
    © 2026 Rainforest Pay, Inc.
  • Show Website
    Payments Strategy Show

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