Payments Strategy Show

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 market
• Three critical payments contract terms to know and how they impact valuation
• Why software companies should own the merchant relationship including sales, support, and pricing
• Key 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

Mindbody is admired as an embedded payments role model by SaaS operators and investors alike.

How can other vertical SaaS platforms replicate their success?

On this episode, Brad Greene (Co-Founder and COO at H3 Partners and former payments leader at Mindbody and HubSpot) joined host Joshua Silver to discuss the rise of embedded payments and how vertical SaaS companies can launch a successful embedded payments offering.

They covered:

• The most frequently overlooked contributors to a successful embedded payments launch (don’t ignore these)
• How Shopify democratized e-commerce and what vSaaS platforms can learn from their success
• 3 factors that drove Mindbody's payments revenue growth and how companies are replicating their success
• The most important consideration when choosing your payments provider (hint: it’s not price)
• How vertical software can still win in the AI era

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

When software companies want to increase payments revenue, payment provider fees are often the first place they look.

But cost cutting yields only a very limited margin increase.

The real growth opportunity is driving greater adoption and payments volume. 

Ashley Willson, co-founder of advisory firm Revolv, joined host Becky Kopplin to share how vertical software companies can grow payments revenue by optimizing their GTM strategy for adoption.

They covered:

• Why vertical SaaS companies need a payments partner, not a vendor, and how to choose the right one for your business
• How to shift the focus from cost savings to volume growth, and why this perspective shift is key for revenue and retention
• One prerequisite that vertical SaaS companies must achieve before adding embedded payments
• 3 things the most successful vertical software companies do right to drive payments adoption, volume, and revenue
• The next big embedded fintech opportunity for vertical software companies

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

Evan DaSilva grew Buildium’s embedded payments volume from $2B/yr to $10B/yr, contributing to a 446% increase in valuation over just 42 months and a $580M acquisition.

Now, Evan is SVP of Payments at donor management and fundraising platform Bloomerang. He joined host Joshua Silver to share his experience as a repeat Head of Payments.

They discussed:

• Why early-stage vertical SaaS founders can’t afford to ignore payments
• Traps to avoid when choosing your first (or next) payment provider
• When to hire a payments leader and what to look for in the ideal candidate
• 3 ways to sell payments into your backbook
• How embedded payments drives higher valuations for vertical software companies

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 most frequently asked questions about surcharging tend to focus on surcharging compliance.

Compliance is important. But the first question should be “is surcharging even the right solution?” 

In this episode, Rainforest VP of Payments Becky Kopplin joins host Joshua Silver to share their insights on both questions. They discussed when to consider surcharging, which problems surcharging does (and does not) solve, and – if you do decide to surcharge – how to be compliant.

This conversation covers:

• Surcharging, convenience fees, technology fees, and discounts – exactly which fee models are subject to surcharging rules and why
• How card networks enforce surcharging rules and the consequences of non-compliance
• 3 must-haves for compliant surcharging and how to approach each
• Hidden costs of surcharging and how to decide if it should be a priority for your platform
• One specific use case where surcharging can significantly accelerate card adoption

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

When vertical software companies transition from referral-based payment providers to an embedded solution, one of the critical challenges is bringing payments support in-house.

Vertical SaaS veterans Emi Keshler and Kyle Scott joined us this week to share their experiences supporting day-to-day operations for embedded payments at vertical software companies, and how to transform payments support from cost center to revenue driver.

We discussed:

• How support and payment operations directly contribute to payments adoption and revenue
• Product gaps that create the vast majority of payments-related support tickets – and how to find and fix them
• Why an internal payments advocate is essential for a profitable payments product 
• How to move from reactive support to proactive support, and become your merchants’ trusted partner
• The hidden decision that can drive 2x revenue when vertical SaaS companies get 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

The chargeback exists to protect consumers. And it assumes that all consumers are good actors. But what happens when they’re not?

First party fraud is increasing by 30% every year.

It’s hard to detect, accounts for more than 75% of chargebacks, and costs US businesses more than $100B per year.

Shanthi Shanmugam, CEO of dispute automation platform Casap, joined guest-host Brooke Smith to discuss how payment providers, ISVs, and merchants can fight first-party fraud.

They covered:

• Why first-party fraud isn’t detected by traditional fraud tooling
• The tradeoff between friction and fraud, and how ISVs can strategically insert friction to reduce first-party fraud 
• How modern technology like first-party fraud scores can identify high-risk consumers
• Why some customers file chargebacks when they’re confused – and a simple strategy to identify (and fix) the most likely causes
• Specific strategies to reduce chargebacks on subscription 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

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