E16: The Pricing Playbook
SAAS Operators25 Heinä 2025

E16: The Pricing Playbook

In this episode of The SaaS Operators, we dive into Prime Day data, shifting consumer behavior, and what it signals about the broader slowdown in e-commerce.


Jeremiah breaks down why Prime Day underperformed and why Amazon is no longer the discovery engine it once was. We explore how DTC brands are getting squeezed and why the winners are pulling further ahead.


Rishabh raises tough questions around pricing strategy, flat-rate ceilings, and whether today’s growth is just pulling forward demand. We talk through SaaS retention, CAC misalignment, and why median order value might be the better metric.


Zach shares how one DTC brand rebuilt their business from the ground up post-tariffs and the pricing insights that unlocked their next wave of growth.


We also go deep on nostalgia-driven investing, broken brand stories like Harley-Davidson and Kodak, and the case for a PE fund that buys and revives brands built on childhood memories.


The episode closes with a debate on flat pricing, competition, NRR tradeoffs, and whether private equity will start using AI agents to turn around bloated service-heavy SaaS companies.

Jaksot(51)

E52: How AI Replaces People with Chase Mohseni from Creative OS

E52: How AI Replaces People with Chase Mohseni from Creative OS

In this episode Jack, Rishabh, Chase and Jeremiah talk about how AI is changing the way they run their teams day to day. Rishabh challenged Chase on why he keeps getting pulled into problems, and his ...

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E50: The Future of Software Businesses with Maxx Blank from Triple Whale

E50: The Future of Software Businesses with Maxx Blank from Triple Whale

This podcast features an in-depth conversation with Maxx Blank, one of the co-founders of Triple Whale. Maxx shares the company's journey from a simple ecommerce dashboard that Maxx wanted for his own...

8 Huhti 54min

E49: How To Build An App That’s Worth Buying with Varun Kundra

E49: How To Build An App That’s Worth Buying with Varun Kundra

In this episode of the SaaS Operators Podcast, Varun Kundra , co-founder of AfterSell, talks about how the business was built around post-purchase upsells on Shopify. The core product sits in the wind...

30 Maalis 53min

E48: From Service to SaaS with Aaron Schwartz & Daniel Brady

E48: From Service to SaaS with Aaron Schwartz & Daniel Brady

In this episode Aaron Schwartz and Daniel Brady, co-founders of Orita, joined us and we talked about how they built an ML-powered audience intelligence product for e-commerce brands. Orita tells you w...

23 Maalis 1h 5min

E47: Building The World’s First AI Creative Strategist with Alex Cooper & Maneesh Apte

E47: Building The World’s First AI Creative Strategist with Alex Cooper & Maneesh Apte

In this episode Alex Cooper and Maneesh Apte, two of the co-founders of Parker, joined us to talk about building an AI creative strategist that lives inside your Slack channel. Parker feels like a sen...

17 Maalis 1h 6min

E46: Acquiring Marketing SaaS & Agencies with Chase Chappell

E46: Acquiring Marketing SaaS & Agencies with Chase Chappell

In this episode Chase Chappell, the founder of Sirge, Success AI, Ads Mastery and Partner at DOE Media, joins us to talk about building a vertically integrated e-commerce operation, acquiring marketin...

9 Maalis 51min

E45: Swiping Left on Ads Like Tinder with John Gargiulo

E45: Swiping Left on Ads Like Tinder with John Gargiulo

In this episode we talked to John Gargiulo, the founder of Airpost. Airpost makes new video ads every week for enterprise advertisers spending $1M or more a month on Facebook ads. They've got human cr...

2 Maalis 54min

E44: 3,500 Customers and Zero Outbound with Shaan Arora

E44: 3,500 Customers and Zero Outbound with Shaan Arora

In this episode we talked to Shaan Arora, the co-founder of Alia, about bootstrapping Alia Popups from $1M to $9M ARR in a year, bootstrapped, with zero outbound, and no venture capital. He started bu...

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