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

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 now
• How to position automation and efficiency as growth levers for SMBs
• Why switching to IC+ pricing doesn’t guarantee more margin
• Pricing, product, and cost optimization strategies to maximize payments margin
• When 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

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 Ed 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 directly
• One dangerous assumption software companies should never make about payments
• Who actually owns your merchant and transaction data if the contract doesn’t specify
• Why states are setting the rules on pricing, subscriptions, and cancellations
• An 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

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

Embedded fintech is a massive opportunity for vertical software companies, but most SaaS operators aren’t thinking about the full potential.

WorkWave SVP & GM of Fintech and Strategic Partnerships Jacob Olins joined host Becky Kopplin to discuss the unique opportunity for vertical SaaS companies to disrupt traditional banking, the most common challenges, and how to unlock fintech growth.

They discussed:

• How Square paved the way for embedded finance
• One leadership decision that separates the embedded fintech winners from everyone else
• Where in the payments journey most software companies get stuck – and how to unlock next level growth
• How to evaluate your embedded fintech opportunities and decide where to start (hint: it’s not always payment acceptance)
• Two archetypes for a payments leader, and how to choose the right payments leader for your organization

Listen to the Acquired podcast episode on Visa that Jacob recommended during the conversation.

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

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