Subscription Stories: True Tales from the Trenches

My final guest of Season Three, Joanna Strober, was the very first guest on the Subscription Stories podcast. Back then, we were talking about Kurbo, the children’s service for WW (that’s Weight Watchers new name). Today, she’s back to talk about her latest venture in direct-to-consumer healthcare, Midi Health. While Kurbo focused on helping kids get to and maintain a healthy weight, Midi is for women at midlife, helping them get better as they get older. You may have noticed my interest in how the way we stay healthy is changing—with guests from Whoop, 30 Madison, Strava, just this season alone. I am fascinated by all of the transformation in the space, as healthcare embraces the concept of a forever transaction. After all, what forever promise is more compelling than more happy, healthy minutes. Healthcare is just embarking on a massive rethinking of how to better align their business models with patient outcomes. Midi is a great example of this. In today’s talk, we cover the consumerization of healthcare and how COVID accelerated the move to digital patient-centric health, the importance of “forever transaction” in treating patients, and the challenges of developing a clear business model in a highly complex environment.   Love the show? Subscribe, rate, review, and share! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook

 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.     Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today:   robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

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.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today:   robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

 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.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today:   robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

  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.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

Season 7 is launching soon, but while you wait, catch up on our most recent season. Some of Season 6's most popular episodes include Best Practices in Subscription Funnel Management with Ken Houseman of the New York Times, Subscription Pricing, Metrics and the Changing Role of the CFO with Maxio’s Randy Wootton and How a Subscription can “Smooth the Lumps” in B2B Services with DDI’s Dr. Tacy Byham. And you don't want to miss out on our most loved episodes of all time, Product-Led Growth for Subscriptions, Using Examples from Medium, LinkedIn and The Athletic with Caitlin Roman, Midi Health’s Joanna Strober on the Ultimate Forever Transaction—Healthcare, and Mighty Network's Gina Bianchini on How to Create a Community Worth Subscribing to. If you haven't listened to these episodes, I encourage you to check them out. And if you like them, please take a minute right now to rate and review them on Apple iTunes or Apple Podcasts. I always ask because it really helps us get the word out. Guests for Season 7 will include Joe Rohrlich, CEO of Recurly, Adam Mayer, Chief Revenue Officer at chess.com, and Mather Economics’ Matt Lindsay, talking about best practices in subscription pricing. To make sure you don't miss a thing, follow Subscription Stories wherever you get your podcasts. Just tap on the follow or subscribe button. And if you like what you hear, please do give us a review and a rating. Thanks for your support, and thanks for listening to Subscription Stories.      Love the show? Subscribe, rate, review, and share! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com

Making pricing simple can be really complicated, especially in the world of subscriptions, where every pricing change can affect how much your members trust you. How do you manage different pricing for different segments? And how do you change that pricing over time? Today's guest, Braeden Russell, is the Director of Pricing for American Home Shield, a home warranty provider with over 2 million members. He needs to optimize the price for the realtors, who often gift the first year of coverage to new homeowners, with the pricing needs of the homeowners themselves, who will eventually be responsible for the relationship. In this episode, you'll learn how to balance the pricing needs of your B2B and B2C members, when to bill monthly versus annually, and how you can use pricing to drive loyalty among your best members.     Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

The subscription stories of publications like The Times, The Wall Street Journal, and Tortoise Media have one person in common, Katie Vanneck-Smith. In her latest role, Katie is going beyond subscriptions. She's leading Hearst UK's efforts to create deep, valuable memberships around each of their 16 specialty magazines, titles ranging from Elle to Men's Health to Good Housekeeping. In this episode, you'll learn how to build a platform that allows for rapid launches of multiple brand memberships, while still incorporating unique features and pricing bundles. You'll also gain insights on how generative AI will and won't affect the publishing world and why the forever promise of news differs from that of specialty content.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

With over 4,600 stores and nearly 1.6 million associates in the United States alone, Walmart is the largest retailer in the world. Walmart+, their membership program, is redefining the contours of paid memberships. I recently had the chance to interview Venessa Yates, Senior Vice President and General Manager of Walmart+, on the main stage at the SubSummit Conference in Dallas, Texas. And I'm delighted to be able to share a recording of our conversation with all of you on the podcast. In this episode, we'll uncover the key elements behind Walmart+’s success and the strategies they've deployed to foster growth and deliver value. You'll also learn how Walmart+ adapts to the evolving needs and expectations of today's consumers to boost engagement, which includes the integration of strategic partnerships into their offering.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

Budgets are tight and competition to get and keep subscribers has never been more fierce. But what if I told you that there was a way to nudge your prospects and subscribers to help them engage more deeply and rapidly? It's possible. Today's guest, Nancy Harhut, has a wealth of easy and inexpensive tactics that can motivate your members to do the right thing at the right time. Nancy is the author of Using Behavioral Science in Marketing and Chief Creative Officer at HBT Marketing. In this special live episode, which was recorded at the SubSummit conference in Dallas, Texas, you'll learn how behavioral science can help you get more from your marketing spend, how to use tools like scarcity, social proof and choice architecture to acquire, engage, and retain your subscribers, and the role of emotion on motivating subscribers to act.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today:     robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

One of the hottest growth areas for subscriptions is farming. Surprising? Maybe. But with small margins and big numbers, efficiency matters. And farming has become an increasingly high tech, high stakes business. Justin Rose is the President of Lifecycle Solutions, Supply Management, and Customer Success at John Deere, a 187 year old company with revenues in 2023 of over 61 billion dollars. You probably know them for their tractors, but they're investing heavily in subscriptions. In today's conversation, Justin and I talk candidly about why this manufacturing company has committed to reaching 10% of annual revenue in software subscriptions by the year 2030, the right and wrong way to accelerate transformation through acquisition, and how to maintain the trust of long standing customers when you change the business model.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today:   robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

Many subscription entrepreneurs lament their lack of fancy software and dashboards to allow them to better manage their business. But if you know your ideal member and understand their pain points, and if you're always tinkering and adjusting your offering to better align with the needs of those members, you can build a powerful recurring revenue business. Even as a solopreneur, this week's guest, James Schramko has developed a unique model to help consultants and experts earn more while working less. And while he has been an early adopter of technology, many of the tools and tactics are flexible enough to be used by large or even very small businesses. More importantly, James has succeeded in building his subscription-based business by focusing on his members and their desired outcomes. Ultimately, membership is about trust and relationships, and James is an expert in both. In today's conversation, you'll learn why bundling too much into your subscription can cost you members, how to use technology to support a global community, and why a tiered ascension model sometimes leaves money on the table.    Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

One of the great mysteries for me is why so many otherwise sophisticated companies don’t focus on involuntary churn. Also known as passive churn or accidental churn, involuntary churn happens when a payment issue raises a flag that causes a merchant to cancel a customer’s subscription. In 70% of these cases, there is no fraud, so the company is literally turning away excellent customers. Involuntary churn routinely impacts about 10% of Annualized Recurring Revenue (ARR), according to some estimates. In today’s episode, Vijay Menon, founder and CEO of Butter Payments, and I discuss what drives involuntary churn, why so many companies underinvest in this problem, and some key tactics to drive revenue growth through better payment management.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts  

Loyalty programs seem to be at a crossroads. Industries including hospitality, financial services, and retail are going beyond the points-based programs we're so familiar with and exploring more personalized, emotionally engaging programs. Some, like CVS, Inspirato, and of course Amazon with Amazon Prime have even incorporated paid loyalty subscriptions which provide benefits in exchange for an annual fee instead of requiring customers to earn benefits through their spending and behaviors. Today's guest, Nadia Popova of Euromonitor International, follows the loyalty trends and provides insights across industries regarding best practices in building long-term relationships with customers. In this wide-ranging conversation, we talk about how consumer expectations have changed since COVID, why personalization is so important, and where subscriptions fit in the broader loyalty landscape.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts  

Loyalty programs have been around forever. Points, cashback, branded credit cards, and now increasingly, we're seeing paid subscription loyalty programs, like Amazon Prime or CVS Care Pass. The goal is the same, to smooth out the lumpy buying behavior common in consumer packaged goods, retail, and hospitality, and to drive habits and engagement. Today's guest, Justin Honaman, leads the worldwide retail and CPG go-to-market team at Amazon Web Services. He also hosts the popular podcast, ContenderCast, where I was a guest a few years ago. In this conversation, Justin and I talk about the changing landscape of loyalty programs, why loyalty is so important right now, and what's driving the rise in these subscription programs.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts  

Building a new subscription model in a large, successful company is hard enough, but when your company's core competency is manufacturing and the subscription involves content and software, you have to do more than build the new business model. You have to change the way the organization thinks about product management. With experience, both at PlayStation and at Ford, today's guest, Ross McGregor, will shed light on how to build a service orientation across a product team. Something critically necessary if you're going to build a forever transaction with your customers. In this conversation, he talks about how to put together the business case that merits a strategic bet on subscriptions, how to build support across the organization from the beginning, and when it's time to scale the experiments.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts  

You're in for a special treat today. My guest, Dr. Tacy Byham, is the CEO of Development Dimensions International, or DDI, a global leadership consulting firm that helps organizations hire, promote, and develop exceptional leaders. A few years ago, I worked with Tacy and her team as they incorporated subscriptions into their business model. The results have been extraordinary. Three years into the launch, over 50 percent of DDI's revenue comes from subscription clients. I've been asking Tacy to share her journey for quite some time, and I'm thrilled that she finally agreed. In today's conversation, we'll talk about how subscriptions can smooth out the lumps in B2B services, how to put together the right team with the right mindset for subscriptions, and how to keep up the momentum after the initial experiments with subscriptions are over.    Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts  

The world of B2B subscriptions has changed a lot since companies like Salesforce first paved the way for what would become known as Software-as-a-Service. And while there are hundreds of marketing and sales-oriented SaaS products, it's taken a lot longer for the subscription model to be fully embraced in the CFO's office. Randy Wootton has seen the evolution of SaaS and understands the changing role of the CFO better than most. He's led businesses focused on sales and marketing solutions at companies like Salesforce, Microsoft, and Rocketfuel, but more recently took over the CEO role at Maxio, a leading provider of billing and financial ops solutions for B2B SaaS companies. In this very rich and full conversation, we talk about why pricing and packaging of subscriptions is so hard, the power of a pricing council, and the changing role of the CFO in a SaaS world.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

If your subscription uses a freemium model, it can be tricky to decide what’s always free, what’s free for a while, and what’s always behind the paywall. Knowing how to manage people at each stage of the funnel can be really challenging. Today’s guest, Ken Houseman, is an expert on both the strategy and the technology required to monetize the funnel for acquisition, upsell, and retention. Today’s conversation isn’t based purely on Ken’s work as VP of Product for The New York Times, and in no way represents the editorial perspective of the organization. Ken’s experience there, as well as his work with organizations, including Oracle, Nike, and even the US military, have shaped his perspective on managing the customer relationship. In this conversation, we discuss why retention is the next obsession for subscription leaders, what needs to be different about how to optimize your ERP for subscriptions, and a few of the less obvious things that can go wrong on the path to conversion.   Love the show? Rate us ⭐️⭐️⭐️⭐️⭐️ and leave a review on Apple Podcasts! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com Twitter Facebook Robbie Kellman Baxter on Instagram Subscription Stories: True Tales from the Trenches on Apple Podcasts

Season 6 is launching soon, but while you wait, catch up on our most recent season. Some of Season 5’s most popular episodes include Mighty Network’s Gina Bianchini returning to subscription stories for a second time to share her wisdom about building purpose-driven communities, as well as Dan Zavorotny of Nutrisense talking about blending hardware, software, and services into a single subscription, and Anne Janzer on subscription marketing. We went deep on customer success with Rod Cherkas, author of the Chief Customer Officer Playbook, and about scaling membership with Pavilion Founder, Sam Jacobs. We talked a lot about subscription product design with Silicon Valley Product Builder, Tom Willerer, Samsara’s CPO, Jeff Hausman, and Mailin Jappé of Acer. I always love conversations with academic researchers with a strong practical mindset, and this season I was happy to host Harvard Business School’s Ava Escarza and Columbia’s Rita McGrath. And we got into the details of two of the trickiest parts of subscription design, pricing and the law, with respectively Mark Stiving, author of Selling Value, and Paavana Kumar of Davis+Gilbert. If you haven’t listened to these episodes, I encourage you to check them out. And if you really like them, please be sure to rate and review them on Apple iTunes or Apple Podcasts. I always ask because it helps us get the word out. Guests for Season 6 include Ken Houseman, who leads product management for the New York Times, Tacy Byham, CEO of the leadership consulting powerhouse DDI, and Randy Wootton, CEO of Maxio. To make sure you don’t miss a thing, follow Subscription Stories wherever you get your podcasts. Just tap on the follow or subscribe button. Thanks for your support and for listening to Subscription Stories.   Love the show? Subscribe, rate, review, and share! Here’s How » Join the Subscription Stories Community today: robbiekellmanbaxter.com