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Payments Strategy Show

Payments Strategy Show

Written by: Rainforest
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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!

© 2026 Rainforest Pay, Inc.
Economics Management Management & Leadership
Episodes
  • Rainforest + PayPal: The future of embedded payments with Taira Hall
    Mar 4 2026

    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


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    25 mins
  • Payment aggregation and contract pitfalls with Edward Marshall and Theresa Kananen
    Feb 4 2026

    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


    Show More Show Less
    30 mins
  • Why market research beats intuition in vertical SaaS with Adam Flemming
    Jan 20 2026

    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


    Show More Show Less
    40 mins
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