Subscription Stories: True Tales from the Trenches

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Robbie Kellman Baxter
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2.0K - 3.3K listeners Neutral 5.0 rating 133 reviews 88 episodes USA
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30s Ad: $77 - $93 60s Ad: $90 - $106 CPM Category: Business
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Subscription models are crazy powerful. Savvy small companies can easily deploy them to knock huge Goliaths off kilter. We’ve seen it in entertainment, software, hardware, news, retail, hospitality—the list goes on. In her podcast series, Robbie Kellman Baxter interviews the leaders of this revolution about how they’re using subscription pricing and membership models to redefine the biggest industries and generate predictable recurring revenue along the way.

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Recent Hosts, Guests & Topics

Here's a quick summary of the last 4 episodes on Subscription Stories: True Tales from the Trenches.

Hosts

Robbie Kellman Baxter

Previous Guests

Mark Garrett
Mark Garrett is the former Chief Financial Officer of Adobe Systems, where he played a pivotal role in the company's transition from traditional software sales to a subscription-based model. Under his financial leadership, Adobe successfully navigated the challenges of this significant business transformation, which ultimately led to a dramatic increase in the company's market capitalization and customer satisfaction. Garrett's expertise in financial strategy and operations has made him a respected figure in the tech industry, particularly in discussions surrounding subscription models and their impact on business performance.
Adam Mayer
Adam Mayer is the Senior Vice President of Monetization at Chess.com, one of the leading online chess platforms globally. With a strong background in revenue strategy and subscription growth, Adam has been instrumental in developing and optimizing Chess.com's premium offerings. His expertise lies in balancing the compelling free tier with the paid subscription model, ensuring that the platform remains attractive to both free and paying users. Adam's insights into user conversion and customer loyalty have made him a key figure in the company's success in the competitive digital landscape.
Matt Lindsay
Matt Lindsay is the founding partner of Mather Economics, a firm specializing in subscription pricing strategies. With extensive experience in helping publishers and businesses develop effective pricing models, he has worked with hundreds of organizations to optimize their revenue and profitability through innovative pricing solutions. His expertise includes addressing pricing controversies and implementing strategies for subscriber retention.
Joe Rohrlich
Joe Rohrlich is the CEO of Recurly, a leading subscription management platform that helps businesses manage their recurring revenue. With extensive experience in the subscription economy, Joe has been instrumental in guiding companies through the complexities of subscription pricing and customer retention strategies. Under his leadership, Recurly has grown significantly, providing innovative solutions that empower businesses to optimize their subscription models and enhance customer relationships.

Topics Discussed

Adobe subscription model business transformation Mark Garrett CFO predictable revenue customer satisfaction financial performance go-to-market strategy subscription business freemium model revenue strategy premium offerings user conversion customer loyalty subscription pricing revenue profitability pricing models introductory offers subscriber retention subscription models recurring revenue 2025 trends digital natives scaling best practices
Episodes

Here's the recent few episodes on Subscription Stories: True Tales from the Trenches.

0:00 40:49

A Behind-The-Scenes Look at Adobe’s Journey to Subscriptions with Mark Garrett, the CFO Who Architected That Transformation

Hosts
Robbie Kellman Baxter
Guests
Mark Garrett
Keywords
Adobe subscription model business transformation Mark Garrett CFO predictable revenue customer satisfaction financial performance go-to-market strategy

 In today's episode, we're exploring one of the most ambitious and successful business model transformations in modern corporate history, the shift of Adobe from a traditional software company selling packaged products to a thriving subscription powerhouse. And who better to walk us through this journey than Mark Garrett, Adobe's former chief financial officer and the architect behind this transition? 

 

When Adobe first announced its move to a subscription-based model in 2011, there was plenty of skepticism. Analysts questioned the financial impact, customers worried about cost increases, and internal teams faced the daunting task of restructuring their entire go-to-market strategy. Mark and his team remained steadfast, not just in their belief that subscriptions would create more predictable revenue, but also that they would allow Adobe to serve customers better with continuous innovation and improved accessibility.

Since those early days, Adobe's market cap has skyrocketed from around 16 billion before the transition to well over 200 billion, proving just how powerful a well-executed subscription strategy can be.

In this conversation, Mark shares the behind-the-scenes story of how Adobe made the leap as a public company, maintaining exceptional financial performance while also enhancing customer satisfaction. We'll discuss the key strategies behind their transition, the biggest challenges they faced both internally and externally, and what other companies can learn from Adobe's playbook. If you've ever wondered how to execute a high-stakes business model transformation, how to balance Wall Street expectations with long-term customer loyalty, or how to design a subscription offering that truly delivers ongoing value, this episode is for you.

 

 

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0:00 40:25

How to Build a Strong Subscription Business While Maintaining a Compelling Free Tier with Chess.com CRO Adam Mayer

Hosts
Robbie Kellman Baxter
Guests
Adam Mayer
Keywords
subscription business freemium model revenue strategy premium offerings user conversion customer loyalty

Chess.com is one of the most popular freemium platforms in the world, offering millions of users free access to an engaging online chess experience. But how do you encourage players to upgrade to a paid tier when the free version is already so compelling?

Adam, with his extensive background in revenue strategy and subscription growth, has played a critical role in designing and optimizing Chess.com's premium offerings.

In this conversation, we'll dive into the challenges and opportunities of building a successful paid tier within a thriving freemium ecosystem, how chess.com balances free and premium value, the strategies they've used to convert free users into loyal subscribers., and the key lessons Adam has learned from his experience leading revenue at a fast-growing digital platform.

If you're interested in learning how to drive revenue without alienating your free user base, how to craft subscription tiers that meet diverse customer needs, and how to foster long-term loyalty in a competitive market, then  you won't want to miss this episode.

 

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0:00 39:31

Controversial Topics in Subscription Pricing with Mather CEO Matt Lindsay

Hosts
Robbie Kellman Baxter
Guests
Matt Lindsay
Keywords
subscription pricing revenue profitability pricing models introductory offers subscriber retention

 Pricing is probably the trickiest, most stressful part of managing a subscription business.

How do you balance revenue and profitability? How can you keep your pricing simple to communicate and execute while personalizing it to optimize for elasticity of demand and value created? If these questions plague your organization, you'll want to take notes today.

Matt Lindsay, founding partner of Mather Economics is a subscription pricing expert who's helped hundreds of publishers build and evolve robust pricing models.

In today's conversation, we're taking on pricing controversies, including the role of introductory offers, how to raise prices and how to respond to a subscriber threatening to cancel.

 

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0:00 39:52

2025 Trends in Subscription Businesses with Recurly CEO Joe Rohrlich

Hosts
Robbie Kellman Baxter
Guests
Joe Rohrlich
Keywords
subscription models recurring revenue 2025 trends digital natives scaling best practices

  When I wrote The Membership Economy, I knew that nearly every organization could build trusted recurring revenue relationships with their customers just by focusing on a forever promise. I really saw a huge future and hoped that companies would follow this path. But what I didn't realize was just how quickly and broadly they would heed my words and invest in subscriptions.

It can be hard to predict what will happen next, but in this episode, we're going to do just that. Today, my guest, Joe Rohrlich, CEO of Recurly, and I will talk about trends for 2025. We'll explore what's ahead, both for digital natives and large companies just dipping their toe into the world of recurring revenue.

You'll learn best practices of the most successful household names, as well as how to manage challenges relating to speed to market and scaling without losing your secret sauce.

 

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Ratings
Global:
5.0 rating 133 reviews
USA
5.0 ratings 113 reviews
Canada
5.0 ratings 11 reviews
UK
5.0 ratings 6 reviews
Ireland
4.0 ratings 1 reviews
Australia
5.0 ratings 1 reviews
New Zealand
5.0 ratings 1 reviews
Singapore
0.0 ratings 0 reviews
South Africa
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