SaaS Therapy

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...

In this episode of SaaS Therapy, Todd and Casey welcome Jillian Betlick, Senior Manager of Community and Customer Advocacy at Calendly. They discuss the importance of community in business, how to build and manage a successful community, and the nuances of community engagement. Jillian shares her insights on finding community champions, measuring success, and handling negative feedback. The conver...

In this episode of SaaS Therapy, Todd and Casey engage with Rachel Provan, a seasoned customer success leader, to explore the intersection of behavioral psychology and customer success. Rachel shares insights on how understanding human decision-making can enhance customer relationships, the importance of empathy in sales, and strategies for effective communication. The conversation delves into com...

In this episode of SaaS Therapy, hosts Todd Kirk and Casey Trujillo celebrate their podcast's success while discussing effective customer training strategies. They explore the new features of Outlook, emphasizing the importance of change management and user comfort. Todd shares best practices for engaging training sessions, highlighting the need to create 'wow' moments for users. The c...

In this episode of SaaS Therapy, Todd Kirk and Casey Trujillo welcome back Ashley DeKerlegand to discuss the Action Mapping framework, a method for enhancing customer education and driving behavior change. The conversation explores the importance of measurable goals, the challenges faced in customer education, and the need for cross-functional collaboration. Ashley shares real-life examples of imp...

In this episode of SaaS Therapy, Todd and Casey dive into the intricacies of change management, focusing on the ADKAR framework and introducing their own ADOPT framework. They discuss the importance of awareness, desire, knowledge, and participation in driving successful software adoption. The conversation emphasizes the need for effective communication strategies, creative campaigns, and the sign...

In this episode of SaaS Therapy, Todd and Casey engage with Sarah Scheibner, a member of the TechSmith Advisory Board, to discuss the importance of customer feedback, change management, and effective communication in software implementation. Sarah shares her experiences with TechSmith and highlights the need for software vendors to prioritize user experience and adapt their strategies to better su...

In this episode of SaaS Therapy, Todd Kirk and Casey Trujillo welcome Bill Wilson, a B2B pricing strategist, to discuss the intricacies of pricing strategies in SaaS businesses. Bill shares his journey from software engineering to pricing strategy, emphasizing the importance of understanding customer needs and the dynamics of pricing within organizations. He outlines a four-step approach to pricin...

In this episode of SaaS Therapy, Todd and Casey welcome Randy Hulme from Qualtrics to discuss the intricacies of customer success in the public sector. Randy shares insights from his extensive experience at Qualtrics, including impactful speakers at their events, the importance of creating a positive team culture, and strategies for managing diverse customer use cases. The conversation emphasizes...

In this episode of SaaS Therapy, host Todd Kirk and guest Ryan Debenham, CEO of Grin AI, explore the evolving landscape of AI in business. They discuss the hype surrounding AI, the balance between optimism and realism, and the importance of understanding AI for both product teams and individual knowledge workers. Ryan shares insights on AI strategy, user experience design, and offers advice for no...

In this episode of SaaS Therapy, Todd talks with Michael Lux, Senior Director of Customer Education at Procore Technologies. They discuss the evolution of Procore from a startup to a public company, the structure of the education team, and the importance of a unified content strategy across departments. Michael shares insights on the challenges of customer education, the need for tailored content,...

In this host only episode of SaaS Therapy, Todd and Casey explore the complexities of decision-making in sales and customer relationships. They introduce the concept of 'Fofu' (fear of messing up) and discuss how it leads to decision paralysis in business. The conversation delves into the importance of emotional intelligence in sales, the different types of questions customers ask during t...

In this episode of SaaS Therapy, Todd Kirk and Sean Adams discuss the importance of customer relationships in the SaaS industry. They explore Sean's unique career path from contractor to VP of Revenue, the significance of measuring customer education impact, and the challenges of navigating customer expectations. The conversation emphasizes the need for SaaS companies to focus on delivering outcom...

In this episode of SaaS Therapy, Todd Kirk and Casey Trujillo chat with Courtney Sembler, Senior Director at HubSpot, discussing the importance of passion in both personal and professional realms. Courtney shares her journey, influenced by her mother's pioneering spirit, and emphasizes the significance of integrating personal passions into work life. The conversation explores how to find one's pas...

In this episode of SaaS Therapy, Todd Kirk and Casey Trujillo engage with John Leh, founder and CEO of Talented Learning, to explore the intricacies of customer education and learning management systems. John shares his unique journey in the learning industry, emphasizing the importance of aligning customer education with business needs and revenue generation. They discuss common pitfalls in the b...

In this episode of SaaS Therapy, Casey Trujillo speaks with Zach Hawley and Will Aja, co-founders of SteerCo, about their journey in customer success and the challenges of startup life. They discuss the importance of empathy in customer interactions, the emotional rollercoaster of entrepreneurship, and how their software aims to automate QBRs to free up time for customer success managers. They emp...