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 roles and strategies in the SaaS industry. The hosts conclude with a call to action for listeners to apply the insights gained and improve their practices in the coming year.Takeaways
Micro passions can guide career alignment and fulfillment.
Effective product training should focus on driving change, not just checking boxes.
Building a strong network is essential for professional growth.
Customer education should be treated as a product, not just a program.
Onboarding processes can provide valuable insights for product improvement.
Reimagining roles can lead to greater success in business.
Practicing fundamentals correctly is key to long-term success.
Engaging with customers during onboarding can enhance product development.
Consistency in efforts leads to better outcomes in customer success.
Feedback from customers is crucial for evolving educational programs.
Contents
00:00 Introduction and Podcast Journey
01:12 Recapping the Top Episodes
02:00 Micro Passions and Career Alignment
08:20 Effective Product Training Strategies
12:01 Networking and Relationship Building
16:28 Customer Education as a Product
22:32 Innovative Onboarding Practices
26:39 Final Thoughts and Homework Assignments
Resources
Credits
Show manager: Jenna Mollinet
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
Contents
00:00 – Intro, T&Cs, and Guest Welcome
01:19 – Eleni’s Journey into Customer Success
03:14 – McDonald’s Story & Why We Quit on Change
04:47 – The Human Side of SaaS Change
07:09 – Calling Out Resistance & Winning Over Curmudgeons
15:16 – Aligning Product, Sales, and CS
18:18 – Change at Scale: Digital CS & AI
19:35 – Getting Sales Bought into Renewals
25:23 – Unlearning Bad Habits & Slowing Down to Speed Up
30:08 – Compensation, Motivation & Multi-Year Deals
36:46 – Intrinsic vs. Extrinsic Motivation in CS Teams
41:03 – Homework: Building Empathy Through Personal Change
43:17 – Final Takeaways & Where to Find Eleni
43:53 – Closing
Resources
Credits
Show manager: Jenna Mollinet
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 check it out!
Resources
Credits
Show manager: Jenna Mollinet
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 customer lifecycle and to orchestrate opportunities for expansion proactively.
Takeaways
Contents
Resources
Credits
Show manager: Jenna Mollinet
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 guiding their teams to recognize and articulate their successes effectively.
Takeaways
People often fail to brag about their successes.
Many in IT take their wins for granted.
It's important to keep others in the loop about achievements.
Some individuals struggle with how to share their successes.
Leaders can help others own their success long-term.
Empowerment is key in self-promotion.
Recognizing achievements can boost morale.
Communication about wins fosters a positive environment.
Helping others articulate their success is valuable.
Celebrating success is crucial for professional growth.
Contents
00:01 — Intro
03:56 — Change management & awareness: why good questions matter
06:13 — High-usage customers: Question #1 – “What’s driving the increased usage lately?”
09:28 — Using top-customer insights: “My best customers do…”
14:43 — CSM role clarified: success owner vs. success coach
18:10 — Sharing wins internally & communicating success
23:30 — Low usage: reframing dips as opportunity
26:47 — Asking what changed in priorities, projects, or org structure
34:09 — Homework recap + LinkedIn cheat-sheet plug & closing
Resources
Credits
Show manager: Jenna Mollinet
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 when working with customers.
Takeaways
What we've tried before when we tried to lead a horse to water, it's just not working.
85% of schools said, my number one problem is I need more leads.
We're looking at the landing pages and we kept coalescing around the same advice.
Your calls to action are clear, but not compelling.
Nobody cares about any of those things.
A bunch of people have the same thing they want more leads.
If I can solve this, I can scale a business.
Big group of people, same problem.
Understanding client needs is crucial for effective marketing.
Compelling calls to action can significantly improve conversion rates.
Contents
00:01 — Intros; meet Dallin Palmer (Halda AI)
01:11 — Accidental entrepreneur → sales mindset shift
03:29 — Halda in a line: AI enrollment + full-funnel agents
05:33 — Why higher ed’s ready for AI (demographics, ROI skepticism, competition)
09:09 — Message shift: “more leads” → full platform
13:38 — Research > shiny tech; weak CTAs insight
16:37 — Core value: “Seek truth” (anti fake-it culture)
21:53 — CS philosophy: strategic partners, empower to fix
30:36 — Run by weekly metrics (GRR/NRR + growth)
33:11 — Biggest churn: VP change; fix with exec reviews, in-person
36:02 — Funding reality: retention > growth
38:00 — Would he do it again? Yes
40:10 — Homework: turn fear into curiosity
Resources
Credits
Show manager: Jenna Mollinet
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 Casey Trujillo explore a fresh framework for evaluating customer education that actually ties learning to product adoption, retention, community strength, and long-term customer value.
Resources
Credits
Show manager: Jenna Mollinet
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 market, the significance of building trust with customers, and the need for proactive management. He emphasizes that success in customer success relies heavily on understanding customer behavior and leveraging data effectively.
Takeaways
The role of Chief Evangelist is crucial for promoting customer success.
Customer success should be proactive, not reactive.
Data-driven strategies are essential for effective customer management.
Healthy tension among leadership teams can drive better results.
Building trust with customers is key to successful relationships.
Customer success teams need to understand customer behavior deeply.
Sales and customer success must align for better outcomes.
The importance of health scores for customer management.
Technology overload is a real challenge for organizations.
Success breeds contentment, which can hinder growth.
Contents
00:00 Introduction to SaaS Therapy and Guest Introduction
01:52 The Role of Chief Evangelist at Gainsight
05:30 Translating the Chief Evangelist Role to Other Industries
08:18 The Consistency of the Customer Success Message
13:10 The Evolving Role of Customer Success Managers
18:44 Strategies for CSMs to Stand Out in a Competitive Market
25:34 Maximizing Product Knowledge for Customer Success
28:50 Building Trust and Driving Change
31:52 The Importance of Healthy Tension in Leadership
39:21 Creating Healthy Tension in Organizations
42:10 The Power of Data-Driven Decision Making
Resources
Credits
Show manager: Jenna Mollinet
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 sales. The conversation also covers the significance of expanding relationships beyond IT, the best and worst sales advice, and strategies for preparing for executive conversations. Carson shares insights on collaboration with team members and finding opportunities in point solutions, concluding with actionable homework for listeners to enhance their sales success.
Takeaways
Your network is your net worth.
Building relationships is key to successful sales.
Trust is earned by understanding customer needs.
AI should be used meaningfully, not just for the sake of it.
Focus on making your customer the hero of the story.
Control the controllables in your sales process.
Small tweaks can lead to significant improvements.
Don't be afraid to reach out to multiple contacts in an organization.
Understand the motivations of your team members for better collaboration.
Sometimes, doing the opposite of your instincts can lead to success.
Contents
00:00 Introduction to SaaS Therapy and Guest Introduction
00:59 Carson Heady's Sales Journey and Background
02:40 Transitioning from Hardware to SaaS Sales
04:20 Key Qualities for Successful Selling
05:38 Building Trust and Understanding Customer Needs
07:28 Navigating AI in Sales Conversations
10:51 Differentiating in a Competitive AI Landscape
14:42 Leveraging AI for Efficiency and Productivity
19:34 Advice for New Sellers and Building Relationships
25:20 Closing Deals with Transparency
27:32 Navigating Tough Conversations
32:05 Collaborating with Team Members
37:20 Building Relationships for Success
41:14 Finding Opportunities in Point Solutions
44:59 Challenging the Status Quo
Resources
Credits
Show manager: Jenna Mollinet
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 conversation emphasizes the need for passion over expertise in community management and the significance of understanding both the company's and the individual's 'why' in community building.
Takeaways
Community is essential for customer engagement and feedback.
Understanding the need for a community is crucial before building one.
Passion is more important than expertise in community management.
Finding and enabling champions within the community can drive engagement.
Measuring success should align with company goals, not just community metrics.
Handling negative feedback requires empathy and understanding.
Community can significantly impact conversion rates.
There is no single path to becoming a community manager; diverse backgrounds are valuable.
Meeting customers where they are emotionally is key to effective communication.
Know your personal and company 'why' to stay motivated in community management.
Contents
00:00 Introduction to SaaS Therapy and Guest Introduction
02:43 The Importance of Community in Business
05:34 Identifying the Need for a Community
08:22 Understanding Community Engagement and Participation
11:09 The Role of Community Managers
14:03 Finding and Empowering Community Champions
17:01 Motivating Community Members
22:37 Optimizing Community Engagement for Business Success
27:50 The Role of Community Managers Across Functions
31:01 Navigating the Challenges of Community Management
33:50 The Importance of Personal and Professional 'Why' in Community
36:19 Handling Negative Feedback in Community Spaces
39:58 Actionable Insights for Community Professionals
Resources
Credits
Show manager: Jenna Mollinet
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 common pitfalls in sales, such as loss aversion and the need to tailor messages for different personas. Rachel emphasizes the significance of listening and understanding the customer's perspective to foster stronger connections and improve retention rates.
Takeaways
Contents
00:00 Introduction to Customer Success Leadership
02:17 Behavioral Psychology in Customer Success
09:28 Understanding Customer Emotions and Decision-Making
15:27 The Power of Framing and Loss Aversion in Sales
19:01 Understanding Audience Dynamics in Customer Success
23:22 Crafting Tailored Messaging for Different Personas
26:46 The Importance of Empathy in Customer Conversations
32:46 Navigating Emotional and Logical Conversations
36:20 Learning from Customer Losses and Moving Forward
Resources
Credits
Show manager: Jenna Mollinet
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 conversation concludes with a challenge for listeners to reevaluate their training approaches and focus on user engagement.
Takeaways
Contents
00:00 Introduction and Celebration of Success
01:09 Effective Customer Training Strategies
04:03 Exploring the New Outlook Features
11:15 Change Management and User Comfort
22:02 Best Practices for Training and Engagement
28:47 Final Thoughts and Challenges for Improvement
Resources
Credits
Show manager: Jenna Mollinet
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 implementing Action Mapping, emphasizing the significance of empathy and understanding in the learning process. The episode concludes with actionable takeaways for listeners to apply the framework in both personal and professional contexts.
Takeaways
Contents
00:00 Intro
2:34 Action Mapping Framework Explained
5:42 Real-World Applications & Challenges
10:36 From Busywork to Measurable Impact
15:19 Shifting from Order-Takers to Advisors
19:20 Executive Sponsorship & Cross-Team Alignment
24:41 Turning Problems Into Solutions
30:57 Practical Examples & MVP Learning
39:18 Why Action Mapping Works
41:26 Wrap-Up & Homework Assignment
Resources
Credits
Show manager: Jenna Mollinet
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 significance of aligning change initiatives with executive goals. The hosts provide actionable insights for SaaS vendors to enhance customer success and drive meaningful change within organizations.
Takeaways
Contents00:00 Intro
1:06 Understanding the ADKAR Framework
4:54 The Importance of Awareness and Desire
8:34 Knowledge and Ability in Change Management
11:32 Effective Communication Strategies
15:44 Innovative Training Approaches
20:40 Introducing the Adopt Framework
20:50 Understanding User Reinforcement and Adoption Challenges
23:44 The Importance of User Orientation in Change Management
27:28 Participation vs. Ability: A Shift in Perspective
32:41 Transforming User Behavior for Lasting Change
36:04 Practical Applications of the Adopt Framework
Resources
Credits
Show manager: Jenna Mollinet
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 support end users. The conversation emphasizes the significance of understanding the user perspective and fostering collaboration between vendors and customers to ensure successful software adoption.
Takeaways
Contents
00:00 Intro
2:02 Exploring the TechSmith Advisory Board
5:56 The Importance of Customer Feedback
11:31 Navigating Change Management in Software
18:04 The Role of Change Management in Software Adoption
25:24 Success Stories in Software Implementation
29:15 Learning from Implementation Failures
35:34 The Importance of Communication in Software Projects
40:35 Homework Assignment for Listeners
Resources
Credits
Show manager: Jenna Mollinet
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 pricing, discusses the significance of customer conversations, and provides insights on when to adjust pricing strategies. The conversation also touches on the importance of aligning pricing with product positioning and handling annual price increases effectively. Bill concludes with actionable homework for listeners to improve their pricing strategies.
Takeaways
Contents00:00 Intro
1:04 Bill Wilson's Journey in Pricing Strategy
2:28 Understanding Pricing Dynamics in Organizations
6:11 The Four-Step Pricing Approach
11:29 Recognizing When to Adjust Pricing Strategies
15:14 The Importance of Customer Conversations
16:50 Navigating Customer Feedback for Pricing
20:42 Rapid Fire Pricing Questions
27:49 Influences and Resources in Pricing Strategy
31:30 Aligning Pricing with Product Positioning
37:29 Handling Annual Price Increases
41:58 Final Thoughts and Homework Assignment
Resources
Credits
Show manager: Jenna Mollinet
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 the need for alignment between customer expectations and company offerings, as well as the significance of understanding value in customer success management. Randy concludes with a homework assignment for listeners to chart their value chain and ensure alignment within their organizations.
Takeaways
Contents
00:00 Intro
2:06 Impactful Speakers and Personal Growth
4:22 Career Development and Job Satisfaction
10:13 Defining Value in Public Sector
11:20 Team Dynamics and Culture Building
18:28 Navigating Company Culture Changes
19:49 Supporting Diverse Customer Needs
22:12 Transforming Data into Actionable Insights
29:10 Customer Success and Value Delivery
35:20 Navigating Consumption Models in SaaS
42:29 Aligning Value Chains for Customer Success
Resources
Credits
Show manager: Jenna Mollinet
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 non-technical workers on embracing AI technology. The conversation emphasizes the need for open-mindedness and continuous learning in the face of rapid technological advancements.
Takeaways
Contents
00:00 Intro
1:01 Ryan's Journey: From Engineer to CEO
2:26 The Current State of AI: Hype vs. Reality
9:40 Navigating AI Fatigue: Balancing Optimism and Realism
10:37 Building AI into Products: Expectations vs. Reality
21:30 AI Strategy: Product vs. Process
23:16 Navigating Product Strategy Risks
27:33 AI for the Average Knowledge Worker
36:22 Homework and Closing Thoughts
Resources
Credits
Show manager: Jenna Mollinet
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, and the metrics that define success in customer training. The conversation also touches on the future of AI in learning and the importance of time to value in customer success.
Takeaways
Contents
00:00 Intro
2:46 Understanding Procore's Structure and Education Role
5:37 Content Strategy and Customer Lifecycle
8:39 Monetization of Education and Professional Services
11:41 Defining Content for Customer Success
14:15 Challenges in Customer Education and Feedback
17:06 Customer Needs and Content Development
20:07 Balancing E-Learning and Instructor-Led Training
22:50 Metrics for Success in Education
25:53 Time to Value and Customer Success Metrics
28:35 Future Aspirations and AI in Learning
31:39 Final Thoughts and Homework Assignment
Resources
Credits
Show manager: Jenna Mollinet
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 the buying process, and the framework of belief, understanding, deciding, and becoming. The hosts emphasize the need for sales professionals to recognize customer mindsets and navigate skepticism and confusion effectively to foster growth and progress in their relationships.
Takeaways
Contents
00:00 Intro
2:40 Understanding Decision Paralysis in Business
5:18 The Importance of Emotional Intelligence in Sales
8:34 Believing Questions: The First Stage of Decision Making
11:02 Understanding Questions: The Next Step in the Process
13:56 Deciding Phase: Operationalizing the Solution
17:51 Becoming: Growing with the Product
20:26 Understanding Customer Individuality
23:06 Identifying Skepticism in Customers
26:22 Addressing Customer Confusion
28:56 Navigating the Decision-Making Process
31:56 Recognizing the Becoming Stage
37:19 Framework for Customer Engagement
Resources
Credits
Show manager: Jenna Mollinet