Payments Strategy Show

Payments Strategy Show
Podcast Description
When vertical SaaS platforms hear about the success of companies like Toast or Shopify at monetizing payments, it’s tempting to think they can just integrate payments and double their revenue overnight. The reality is a bit more complex, and a lot of SaaS companies miss out on the full revenue potential because their payments product, positioning, or pricing is a little off. Seemingly insignificant details of the payments implementation and go-to-market strategy can have a disproportionate impact on the financial success of a payments offering.Join host Joshua Silver in conversations with SaaS leaders, investors, and industry experts to illuminate the details that actually move the needle – so you can optimize your payments offering for maximum adoption, revenue, and enterprise value.
Podcast Insights
Content Themes
The show focuses on payments integration within SaaS, examining topics such as common pitfalls in choosing payment providers, strategies to enhance adoption rates, essential contract terms, and the impact of organizational structure on payment success. Episodes include explorations of why 85% of SaaS payment offerings underperform and how to navigate the complexities of the fintech landscape.

RETURNING SEPTEMBER 16th 2025
When vertical SaaS platforms hear about the success of companies like Toast or Shopify at monetizing payments, it’s tempting to think they can just integrate payments and double their revenue overnight.
The reality is a bit more complex, and a lot of SaaS companies miss out on the full revenue potential because their payments product, positioning, or pricing is a little off.
Seemingly insignificant details of the payments implementation and go-to-market strategy can have a disproportionate impact on the financial success of a payments offering.
Join host Joshua Silver in conversations with SaaS leaders, investors, and industry experts to illuminate the details that actually move the needle – so you can optimize your payments offering for maximum adoption, revenue, and enterprise value.
New episodes biweekly on Tuesdays!
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
September 9th, 2025 in San Francisco, CA
https://www.vertexconference.com/
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

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