Unlocking HSA/FSA payments for vertical SaaS with Truemed’s Chris Shaw

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 [https://coastpay.com/] Founder and CEO, Daniel Simon [https://www.linkedin.com/in/danielksimon/] joined host Joshua Silver [https://www.linkedin.com/in/joshuasilver/], 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/ [https://www.vertexconference.com/] Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference [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 [https://rainforestpay.com] Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay [https://linkedin.com/company/rainforestpay]

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 [https://www.evercommerce.com/everhealth/]’s Head of Payments, Savannah Krieg [https://www.linkedin.com/in/savannah-krieg/] joined host Becky Kopplin [https://www.linkedin.com/in/becky-kopplin-9764a03/], 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/ [https://www.vertexconference.com/] Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference [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 [https://rainforestpay.com] Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay [https://linkedin.com/company/rainforestpay]

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 [https://www.linkedin.com/in/pamela-draper-3b39017/], President of Digital Commerce Payments [https://dc-payments.ca/] joined host Joshua Silver [https://www.linkedin.com/in/joshuasilver/], 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/ [https://www.vertexconference.com/] Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference [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 [https://rainforestpay.com] Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay [https://linkedin.com/company/rainforestpay]

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 [https://www.truemed.com/] Head of GTM Partnerships, Chris Shaw [https://www.linkedin.com/in/mochrisshaw/] joined host Aaron Steinberg [https://www.linkedin.com/in/aaronmsteinberg/], 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/ [https://www.vertexconference.com/] Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference [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 [https://rainforestpay.com] Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay [https://linkedin.com/company/rainforestpay]

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 [https://www.unit.co/] CEO and Co-Founder, Itai Damti [https://www.linkedin.com/in/itaidamti/] joined host Joshua Silver [https://www.linkedin.com/in/joshuasilver/], 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/ [https://www.vertexconference.com/] Get updates on LinkedIn: https://www.linkedin.com/company/vertex-vertical-software-conference [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 [https://rainforestpay.com] Connect with us on LinkedIn: https://linkedin.com/company/rainforestpay [https://linkedin.com/company/rainforestpay]