Payments Strategy Show – Details, episodes & analysis

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

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

The Automated Clearing House (ACH) network moved $86 trillion in the U.S. in 2024 – more than 7x the four major card networks combined.

Yet the big embedded payment providers treat ACH as an afterthought. 

On this episode, Rainforest Founder and CEO Joshua Silver joins guest host Brooke Smith to discuss how software companies can drive more payments volume and revenue with ACH.

They covered:

• Why ACH is still the backbone of U.S. money movement, and will continue to be for a while
• Deep dive into the mechanics, timelines, and risk profile of ACH vs credit cards
• Modern tools that can reduce the risk of ACH for merchants, software platforms, and payment providers
• How to monetize embedded ACH payments by selling the value of the whole solution
• 3 ways to encourage end customers to pay online instead of mailing a check, so you can increase embedded payments utilization (and volume!)

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

Will AI erode vertical SaaS? How can vertical software companies win market share when enterprise customers can use AI to build their own systems?

Vertical software founder, CEO, and investor Luke Sophinos joined Rainforest VP of Revenue Aaron Steinberg to discuss the future of vertical SaaS. 

They covered:

• Why focusing on just one or two core values can help software companies build a strong team
• Luke’s proven playbook for success in vertical SaaS, and how AI is changing it
• The biggest mistake startups make when building AI products and what to do instead 
• One prerequisite vertical software platforms must have before adding payments
• How vertical SaaS companies can win their market by becoming the system of record

Mentioned on this episode:

Luke Sophinos: https://lukesophinos.com/

Luke’s newsletter: https://www.newsletter.lukesophinos.com/ 

Vertex: The Vertical Software Conference

September 9th, 2025 in San Francisco, CA

https://www.vertexconference.com/ 

Vertical Software Summit

October 16th and 17th in Miami, FL

https://www.verticalsaasgroup.com/vertical-software-summit 

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

What does it take to grow a SaaS company from pre-revenue to market leader or scale to a successful exit?

Kevin Lee has been a software and payments leader for more than 25 years and his track record includes multiple successful exits. He joins host Joshua Silver to discuss the the rise of embedded fintech, how the strongest SaaS companies are approaching embedded payments, and why the most promising SaaS companies are selling all-in-one solutions.

They covered:

• How payments combined with business intelligence makes the core SaaS product sticker (and a real-world example)
• The hidden cause of low adoption and how to prevent it
• Why Stripe is no longer the default choice for embedded payments
• How to choose a payment provider that won’t steal your merchants (this is more common than you think)
• Overcoming common objections when selling embedded payments to existing customers

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

How can a vertical SaaS company become THE operating system for their industry?

Fintech board member, investor, and advisor Bob Butler joins Rainforest VP of Payments Becky Kopplin to discuss how vertical software companies become the system of record with robust vertical workflows and embedded fintech.

They covered:

• One thing Bob would do differently if he was building a payments company all over again
• Contract terms to align incentives with your payment provider
• The critical metric that matters more than margin – and how to optimize for it
• Critical org structure and culture mistakes that hinder payments growth
• How a great embedded payments experience defeats low cost competitors (and a simple test to evaluate if you got it right)

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

One of the biggest challenges for software companies launching embedded payments is adoption. How do you get customers to use embedded payments?

Roofing CRM platform ProLine didn't have this problem.

Customers asked for payments. And, when ProLine launched their embedded payments, customers eagerly moved their payments volume to the platform.

On this episode, ProLine Co-Founder and CEO AJ Briley joined host Joshua Silver to share how ProLine worked closely with customers to build the right product and get adoption so quickly:

• Why iteration is essential to building a great product
• How customer feedback helped Proline build a winning product
• Choosing the right payment provider, and when it makes sense to engage a consultant
• Specific features in the core product that drove Proline’s success with payments
• How embedded payments can increase company valuation

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

Basis Theory Co-Founder and CEO Colin Luce joins Rainforest Founder and CEO Joshua Silver to discuss the future of agentic commerce.

They covered:

• Shopping in an AI-enabled ecosystem vs true agentic commerce
• How certain categories of shopping are likely to adopt AI
• Will agentic commerce drive more shopping (and payments volume) or make shopping more efficient?
• Data and infrastructure needed to power agentic commerce
• Risk management implications of empowering AI agents to make buying 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

In this episode, Basis Theory Co-Founder and CEO Colin Luce joins Rainforest Founder and CEO Joshua Silver for a deep dive on payments orchestration, tokenization, and vaulting.

They discussed:

• The number one reason to invest in payment orchestration (hint: it's not least-cost routing)
• How software companies can protect their merchant onboarding data and get more control over their payment processing
• The sneaky retention tactic some legacy payment providers still use -- and how data vaulting can help software platforms break free
• Why the promise of "use network tokens and save 10 bps" has yet to be realized
• Exactly what is Payments 3.0, and the capability it is unlocking for software platform

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

Payments pundits tend to say things like “every software company will be a payments company”... but how should software companies really evaluate the payments opportunity?

Andrew Mosawi has helped hundreds of software companies set up and scale their payments businesses, and on this episode he joins host Joshua Silver to share his key insights.

They covered:

• When to bring in a dedicated payments leader (hint: it’s not a certain ARR or processing volume)
• Specific questions to help you decide if payments should be a priority right now
• Why payment provider selection should NOT be the first milestone, and what SaaS leaders need to do before that
• 3 ways to create value in your software business with payments (and none of them involve being the lowest cost option)
• The next big embedded fintech opportunity for vertical software companies, and how to prepare for it

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