SaaS Therapy

Summary: In this episode of SaaS Therapy, Todd Kirk hosts Chandler Milne from Brainstorm to discuss the science of learning experience design, change management, and how to effectively drive organizational transformation. They explore strategies for shaping environments, engaging stakeholders, and leveraging AI to enhance learning outcomes. Chapters: 00:00 Introduction to SaaS Therapy 01:31 Unders...

Summary: Justin Watt, CEO of Switchboard, shares insights on AI adoption, change management, and how SaaS companies can stay relevant in the rapidly evolving AI landscape. Learn practical strategies for understanding customer needs, implementing AI responsibly, and preparing for the future of AI-driven SaaS solutions. Key Topics AI decision-making and governance Change management and user adoption...

In this episode of SaaS Therapy, Todd Kirk and Casey Trujillo interview John Wade, principal of Brainstorm, to explore the human side of AI adoption, the evolution of learning models, and practical strategies for integrating AI into business and personal growth. They discuss the importance of mindset, organizational change, and taking incremental steps to harness AI's power effectively. Takeaw...

Casey explores how hard customer education is for the customer’s point of contact. Using one SaaS example, he shows how private portals, automated communications, adaptive learning, and reporting can save time, scale training, and improve adoption without adding manual work. Key takeaways Customer education often creates hidden labor Manual comms slow down adoption Data helps customers act strateg...

In this special podcast episode, Courtney Sembler explores how to modernize customer education without rebuilding from scratch. It highlights shifting learner expectations, the growing gap between traditional training and real outcomes, and introduces a blended approach combining structured learning, microlearning, and adaptive experiences to drive product adoption, measurable impact, and long-ter...

Customer onboarding is evolving from a checklist into a value-driven growth engine. Donna Weber explains why delivering meaningful customer outcomes—not just completing onboarding steps—is critical for retention, expansion, and success. Companies must shift from internal processes to customer-centric value, using interviews, data, and phased wins to drive long-term adoption and business impact. Ta...

In this episode of SaaS Therapy, Todd and Casey challenge the myth that customer education should be judged by whether it reduces support tickets. Instead, they argue that strong training should reduce basic, repetitive questions while increasing higher-value questions that reflect deeper adoption, smarter workflows, and stronger long-term customer success. Takeaways The difference between custome...

In this episode of SaaS Therapy, Todd and Casey interview Kat Breeggemann, founder of Katalyst CX, to debunk myths about digital customer success. They explore how digital CS strategies can be effectively applied across all customer segments, the importance of multi-channel communication, and practical tips for implementation. Takeaways Why digital customer success is more than just email and shou...

In this episode of SaaS Therapy, Todd and Casey are joined by Nicolette Stepakoff, VP of Change and Enablement at Eliza. They discuss the critical role of change management in the adoption of AI technologies within organizations. Nicolette shares her journey from sales to change management, emphasizing the importance of understanding user needs and executive sponsorship in successful AI implementa...

In this episode of SaaS Therapy, hosts Todd and Casey engage with Amy Konary, a thought leader in the SaaS industry. They explore Amy's journey from traditional software licensing to the innovative world of SaaS, discussing the evolution of pricing models, the impact of AI on pricing strategies, and the importance of customer relationships. The conversation emphasizes the need for a shared ris...

In this episode of SaaS Therapy, Todd and Casey welcome back Courtney Sembler, who shares her journey from HubSpot to AlignCX. The conversation delves into the importance of customer education in SaaS organizations, setting expectations for its impact, and the necessity of content maintenance. They discuss the role of customer education in driving revenue and improving customer success, as well as...

In this episode of SaaS Therapy, Todd and Casey chat with Kelly McNamee, Director of Customer Learning at Point Click Care, to explore the Six Sigma framework and its application in customer education. They discuss how Six Sigma helps organizations identify inefficiencies, prioritize changes, and enhance customer experiences. Kelly shares concrete examples of using Six Sigma principles to solve re...

In this episode of SaaS Therapy, hosts Todd Kirk and Casey Trujillo are joined by Andrea Nottingham, a seasoned Customer Success Manager. They discuss the transition from being a customer to a CSM, the importance of defining success for clients, and best practices for managing customer relationships. Andrea shares insights on handling renewals, building trust, and navigating organizational dynamic...

In this episode of SaaS Therapy, hosts Todd Kirk and Casey Trujillo explore the myth that customers don't have time for training. They discuss the underlying reasons behind this belief, emphasizing the importance of understanding customer needs and perceptions. The conversation highlights the significance of training type, the role of support sites as indicators of training needs, and the inef...

In this episode of SaaS Therapy, Todd and Casey discuss the challenges of AI adoption in SaaS organizations. They explore the reasons behind low user engagement with AI tools, emphasizing the importance of customer education and understanding user needs. The conversation highlights the necessity for SaaS vendors to develop clear strategies and effective communication to guide their customers in ut...

In this episode of SaaS Therapy, hosts Todd and Casey engage with Jacqueline Sayler, an enterprise account manager, discussing the intricacies of customer success and negotiation strategies. Jacqueline shares her journey from discomfort in discussing renewals to mastering the art of negotiation through experience and preparation. The conversation delves into a real-life renewal case, highlighting...

In this episode of SaaS Therapy, hosts Todd and Casey reflect on their podcast journey during season 5, discussing the top episodes of the season. They explore themes such as micro passions, effective product training, the importance of networking, and the need to treat customer education as a product. The conversation emphasizes innovative onboarding practices and the significance of reimagining...

The conversation delves into the complexities of change management in the SaaS industry, emphasizing the psychological aspects that influence user adoption. Eleni Vorvis discusses the importance of understanding user motivation and the need for a structured approach to facilitate smoother transitions for customers. Takeaways Change management is hard, particularly in SaaS. We don't think about...

In this recap episode, Casey highlights Lincoln Murphy as he shared his insights on the evolution of Customer Success and what it truly means to build customer relationships that last. From redefining retention and expansion to aligning CS with business outcomes, Lincoln breaks down practical strategies for creating real value and driving long-term growth. If you haven't given it a listen, go...

The conversation delves into the concept of customer success and its direct correlation with business expansion. It emphasizes the importance of understanding customer journeys and creating structured paths for customers to achieve success, which in turn leads to increased consumption of services or products. The discussion highlights the need for businesses to recognize progress milestones in the...

In this conversation, Todd Kirk and Casey Trujillo discuss the often-overlooked importance of celebrating personal and professional successes, particularly in the IT field. They explore how individuals frequently fail to share their achievements and the need for empowerment in communicating these wins to others. The dialogue emphasizes the significance of self-promotion and the role of leaders in...

SaaS Therapy hosts Todd Kirk and Casey Trujillo talk with Dallin Palmer, co-founder of Halda AI, about building an enrollment marketing platform for universities, why higher ed is surprisingly open to AI, and how “seeking truth” (not vanity metrics) drives real customer value. Dallin shares hiring and CS practices, product prioritization, and a simple homework assignment: flip fear into curiosity...

Welcome to SaaS Therapy — the show where founders stop pretending everything’s perfect. Hosts Todd Kirk and Casey Trujillo pull back the curtain on the real SaaS journey: the wins, the setbacks, the stress, and the breakthroughs. If you’re building, scaling, or dreaming about the SaaS life, grab a seat. This is your weekly dose of honest stories and real-talk advice. In this episode, Todd Kirk and...

In this episode of SaaS Therapy, Todd Kirk and Casey Trujillo interview Dan Steinman, a seasoned expert in customer success and former Chief Evangelist at Gainsight. The conversation delves into the evolving role of customer success, the importance of data-driven strategies, and the necessity of healthy tension within leadership teams. Dan shares insights on how to stand out in a competitive SaaS...

In this episode of SaaS Therapy, host Todd Kirk and co-host Casey Trujillo welcome Carson Heady, a sales expert from Microsoft. They discuss Carson's extensive sales background, the transition from hardware to SaaS, and the essential skills for successful selling. Carson emphasizes the importance of building trust with customers, understanding their needs, and navigating the complexities of AI...