Hard Calls with Trisha Price

Remember the SaaS playbook that built today’s tech giants? Well, it’s officially dead. The AI revolution is rewriting the rules, leaving companies without a roadmap for what comes next. However, Pendo CEO and co-founder, Todd Olson, is mapping out a new playbook using insights from customers, other founders, and his own team, all of whom are either beginning and in the midst of their AI transformations.In this episode, host Trisha Price and Todd unpack how leaders can thrive when everything they know gets turned upside down. This isn’t your typical founder interview - it’s an open, honest conversation about leading when there’s no playbook to follow.Here’s what you’ll discover:“There’s no AI playbook. …Even the AI-native founders are just experimenting like the rest of us.” - Todd OlsonThe power behind an entrepreneurial spirit. Todd shares his thoughts on what the role of a CEO needs to be during a transformation. And why his majors and minors, along with his entrepreneurial mindset, are exactly what the company needs from him right now. Todd’s lesson: Have the conviction to show that your idea can work.How Pendo went all-in on AI. Todd reveals the strategy behind acquiring AI-native companies over established players, and how injecting new DNA changed everything from engineering practices to innovation. He also shares how his role in experimenting with AI tools inspired the rest of the company.How to balance AI innovation with enterprise expectations. Todd explains the balancing act he and his team face with enterprise customers who still expect familiar and compliant solutions, while simultaneously introducing AI agents and workflows to guide the company through an AI transformation. Whether you’re a founder trying to reinvent your business model or a product leader tasked with building your company’s AI strategy, this episode reveals what it actually takes to lead with entrepreneurial conviction when the only certainty is change.Love the episode?Drop us a  ⭐⭐⭐⭐⭐  review, and share this episode with a teammate who’s staring down their own hard call today. Every subscription and review helps more product leaders find the show - let’s build better products together!Presented by Pendo. Dive deeper at pendo.io or connect with Trisha Price on LinkedIn.

What do you do when a customer asks for a feature that isn’t on your roadmap? In this episode of Hard Calls, Trisha Price and Mark Mitchell, Chief Product Officer at Morgan Stanley at Work, share personal, candid stories of the hardest calls Mark has made - starting with knowing when to walk away from a big prospect that just isn’t the right fit. Mark breaks down how he weighs effort, impact, and adoption when deciding which product investments to make and why “massive size, small impact” requests are the real landmines.Balancing strategy, execution and priorities is always challenging for product leaders, but Mark shares his 90-day-9-month-9-year time-horizon framework, and you’ll be surprised how easy it is to manage.They go deep on user adoption as the north-star KPI, the “whole product” motions that actually drive it, and the customer focus that keeps product, sales, marketing, and education aligned. What makes for a great product organization? “For us, it starts with us making sure that we understand the needs of the customer. Understand the needs of the problem and the problem that we're trying to solve, and spend a lot of time understanding the front side of discovery and planning and all the things that go into building a great product.”Finally, Mark shares how a highly regulated financial services enterprise, such as Morgan Stanley at Work, is embracing AI—from code assistance to internal copilots—and why he believes AI will soon be a prerequisite input for product decisions. Whether you're navigating short-term pressures or long-term strategy, new to product or a seasoned leader, this episode will add to your knowledge base to help you make smarter product bets and deliver value at scale. Love the episode? Download and listen to Hard Calls every two weeks in your favorite podcast app, drop us a ⭐⭐⭐⭐⭐ review, and share this episode with a teammate who’s staring down their own hard call today. Every subscription and review helps more product leaders find the show—let’s build better products together!Presented by Pendo.Explore more insights at pendo.io or connect with Trisha Price on LinkedIn.

Vantaca is bringing AI innovation to an industry in desperate need of disruption - community management or HOAs. Vantaca CEO, Ben Currin joins Trisha Price in this episode of Hard Calls and talks about how Vantaca is wrapping AI and agentic workflows into traditional SaaS software to improve the way we work with each other and agents.Product leaders from any industry will gain great insights into how to think differently about their AI projects. You’ll hear about the lessons learned when the team goes all in on letting go of old mindsets, processes, and sunk costs to create a scalable AI strategy that anyone can benefit from. Ben shares how an acquisition made Vantaca’s AI vision take hold and scale its AI roadmap. You’ll also be surprised to hear his story about how understanding the basics of a car, such as the steering wheel and brakes, is the same thinking that product managers should apply to create a great user experience, and the three things he does to balance these two priorities. The two also discuss the benefits Vantaca has gained by becoming product-led and how staying close to the customer allows them to develop and iterate better products using some fun new AI tools.Love the episode? Download and listen to Hard Calls every two weeks in your favorite podcast app, drop us a ⭐⭐⭐⭐⭐ review, and share this episode with a teammate who’s staring down their own hard call today. Every subscription and review helps more product leaders find the show—let’s build better products together!Presented by Pendo.Explore more insights at pendo.io or connect with Trisha Price on LinkedIn.

In this episode of Hard Calls, host Trisha Price sits down with Jessica Soroky, product operations leader turned Chief of Staff to the CEO at Engine. The two discuss the symbiotic relationship between product operations and a successful product organization. Their conversation offers an inside look at what operational excellence really looks like and the hard calls it takes to achieve it in your company.A few highlights from the episode:The hard call Jessica had to make to let go of a well-liked team member in order to get her team operating at the next level.How  product operations, when done well, can get more out of your product organization without having to add additional heads. Shifting the product shipping mindset from “done” to “delivered” using the product development lifecycle to make sure that the products built are as successful as possible.Love the episode? Subscribe to Hard Calls in your favorite podcast app, drop us a ⭐⭐⭐⭐⭐ review, and share this episode with a teammate who’s staring down their own hard call today. Every subscription and review helps more product leaders find the show—let’s build better products together!👀 Connect with Jessica Soroky on LinkedIn → https://www.linkedin.com/in/jessicasoroky/ 🔗 Learn more about Pendo at pendo.io 📬 Follow Trisha Price on LinkedIn → https://www.linkedin.com/in/trisha-price-3063081/

Marty Cagan, a seasoned partner at Silicon Valley Product Group and author of several influential books, shares pivotal insights from his extensive product management career. He delves into the challenges faced during the PayPal integration at eBay and the value of user feedback. The conversation emphasizes transforming product mindsets, building trust within teams, and the importance of collaboration between product and sales. Additionally, Marty discusses balancing intuition with data in decision-making and embracing learning for innovation in product development.

Pierre Naudé, the Founding CEO and Executive Chairman of nCino, shares valuable insights from his journey of scaling nCino from startup to public company. He emphasizes the importance of adaptable leadership and strategic decision-making in navigating team dynamics during rapid growth. Naudé discusses redefining organizational structures to foster innovation and the critical nature of hiring the right individuals for team success. Together with Trisha Price, they reflect on essential leadership lessons and the impact of AI on product management.

Every product leader has to make them: the high-stakes decisions that define outcomes, shape careers, and don't come with easy answers.The Hard Calls podcast, hosted by Trisha Price, features candid conversations with product and tech leaders about the pivotal decisions that drive great products and the pressure that comes with it. From conflicting priorities and unclear success metrics to aligning teams and navigating executive expectations, you will hear compelling stories and best practices that drive business outcomes and help you make the Hard Calls.Real decisions. Real stakes. Real leadership.Presented by PendoLearn more at pendo.io/Follow Trisha Price on LinkedIn