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