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SaaS Therapy
By BrainStormBusiness
SaaS Therapy episodes
- How to Drive Adoption in Large Organizations with Ashley Moore
Summary
In this insightful episode, Ashley Moore shares her extensive experience in change management, digital transformation, and employee experience. She discusses effective strategies for driving change, creating psychological safety, managing change fatigue, and the importance of human connection in technology adoption.
Key Topics
Change management principles and frameworks
Strategies for effective employee communication
The role of middle managers in change success
Creating a safe environment for change
The impact of human connection in digital transformation
Chapters
00:00 Introduction to Change Management and Employee Experience
03:01 The Role of Change Agents in Digital Transformation
05:43 Understanding Psychological Safety in Change
08:47 The Importance of Human Connection in Technology
11:32 Effective Communication Strategies for Change
14:11 Managing Change Fatigue in Organizations
17:21 Empowering Middle Managers for Successful Change
19:50 Debunking Myths in Change Management
22:44 The Necessity of Continuous Change Management
25:16 Final Thoughts and Homework Assignment
31:29 SaaS Therapy Outro .mp4
Resources:
Connect with Casey
Connect with Todd
Visit the show page
Get to know BrainStorm
Credits:
Show direction: Debra Wilson
Show design: Kensie Smith
Show manager:Adam Rockwood
32 min - How to Shape Environments for Better Learning with Chandler Milne
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 Understanding Learning Experience Design
03:00 The Importance of Change Management
07:38 The Human Element in Learning
09:44 Destination Learning vs. Modern Learning
12:35 Customer Education's Role in Business Outcomes
15:13 Navigating Change in Organizations
17:41 Empowering Employees in Change Management
22:48 Becoming a Visible Leader
23:48 Leveraging AI for Change Management
26:28 Innovative Approaches to Change
30:17 Shaping the Environment for Change
34:08 Navigating Remote Work Dynamics
36:44 Assessing Readiness for Change
39:03 The Reality of Change Management
42:25 Empowerment and Intentionality in Change
Guest Information:
Chandler Milne on LinkedIn
The Right Click on YouTube
Resources:
Connect with Casey
Connect with Todd
Visit the show page
Get to know BrainStorm
Credits:
Show direction: Debra Wilson
Show design: Kensie Smith
Show manager:Adam Rockwood
46 min - How to Build AI-Ready SaaS Products with Justin Watt
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
- Building AI-integrated SaaS solutions
Chapters
00:00 Introduction to SaaS Therapy and Guest Background
01:08 Justin Watt's Expertise and Switchboard's Mission
03:06 Understanding Customer Needs in AI Adoption
04:36 Challenges in Decision-Making for AI Tools
06:16 The Role of Business vs. Technical Decision Makers
07:58 The Importance of Change Management in AI Implementation
09:40 Evaluating AI Solutions: Off-the-Shelf vs. Custom Builds
11:43 Best Practices for Customer Success Managers
13:02 Navigating Customer Conversations on AI Tools
16:16 Overcoming Barriers in SaaS AI Implementation
19:11 Consultative Sales Approach in SaaS AI Solutions
20:41 Navigating Customer Conversations in SaaS
23:57 The Importance of Understanding Customer Processes
28:37 Change Management and AI Adoption
31:20 Warnings for SaaS Companies in the Age of AI
36:12 Homework for SaaS Professionals: Defining Success
41 min - People First, Technology Second with John Wade, Principal @ BrainStorm
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.
Takeaways
Technology adoption is fundamentally a human problem Most software goes unused due to people gaps AI success depends on human behavior changeTraining models are outdated and inefficientAI creates endless, personalized use possibilitiesOrganizations must prioritize adoption through leadership structuresSmall, consistent actions drive meaningful progressFocus on opportunity, not fear, with AI
Content
00:00 Introduction to SaaS Therapy and Guest Introduction
02:37 The Role of AI in SaaS and Customer Engagement
05:23 Understanding Human Behavior in Technology Adoption
08:09 Balancing Individual and Organizational Success
10:35 The Evolution of Learning in Technology
15:07 Challenges in Training and Adoption of New Technologies
19:38 The Divergence of AI and SaaS Applications
22:04 Human Adaptation to AI Technology
24:09 Implementing AI in Organizational Structures
27:01 Driving Change Through AI Adoption
31:25 Navigating the AI Landscape
34:28 Finding Opportunity in AI Challenges
Resources
Connect with Casey
Connect with Todd
Visit the show page
Get to know BrainStorm
Credits
Show direction: Debra Wilson
Show design: Kensie Smith
Show manager: Jenna Mollinet
Show manager:Adam Rockwood
48 min - The Hidden 150 Hours Behind Customer Adoption with Casey Trujillo
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 strategically
- Training must scale beyond live sessions
- Simplicity drives stronger product awareness
Content
- 0:01 Intro and Todd’s absence
- 0:32 Setting up the customer example
- 1:13 What the private portal included
- 2:23 Why customer-sent comms work better
- 4:11 The 150 hours saved insight
- 5:19 Why manual communication breaks down
- 6:45 Why two people cannot train 8,000 users
- 9:08 How 700 employees were trained in under 30 days
Resources
Connect with Casey
Connect with Todd
Visit the show page
Get to know BrainStorm
Credits
Show direction: Debra Wilson
Show design: Kensie Smith
Show manager: Jenna Mollinet
14 min - WEBINAR SPECIAL: Modernizing your academy without starting over with Courtney Sembler, COO @AlignedCX
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-term customer value.
Takeaways
Learner expectations are rapidly evolvingGap between training and expectations is growingOutcomes matter more than completion ratesDon’t rebuild—modernize what already worksMicrolearning must support real user actionsBlend structured and short-form learningPersonalization drives engagement and adoptionData is essential to prove business impact
Content
- 00:00 Intro and speaker welcome
- 02:04 Webinar focus: modernizing academies
- 06:20 Changing learner expectations and behaviors
- 09:13 Rise of microlearning and self-paced learning
- 11:25 Shift from metrics to business outcomes
- 16:07 Tension: change vs preserving value
- 18:42 Old vs new success metrics
- 21:29 Real example: better support outcomes
- 25:23 Common fears in transformation
- 27:15 Reframe: evolve, don’t rebuild
- 32:10 Microlearning vs micro content distinction
- 38:26 Designing for modern learners
- 51:43 Four-phase modernization approach
Resources
Connect with Casey
Connect with Todd
Visit the show page
Get to know BrainStorm
Credits
Show direction: Debra Wilson
Show design: Kensie Smith
Show manager: Jenna Mollinet
Show assistant: Adam Rockwood
55 min - Onboarding Doesn’t Matter with Donna Weber, CEO @Springboard Solutions
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.
Takeaways
Onboarding fails without delivering meaningful customer value outcomesInternal focus prevents teams from understanding real customer needsTime to first value is often poorly defined and measuredCustomers care about outcomes, not features or product setupQuick wins create dopamine and drive continued engagementValue measurement should align with company-level revenue goalsCustomer interviews reveal insights surveys often fail to captureOnboarding success requires ongoing evolution, not one-time optimization
Content
00:00 – Intro and guest background
02:00 – Why onboarding needs rethinking
06:10 – Defining real customer value
10:00 – Identifying key value moments
11:20 – Onboarding assessment framework overview
19:30 – Sales to implementation handoff gap
22:45 – Quick wins vs complex onboarding
32:40 – Measuring success and key metrics
Resources
Connect with Casey
Connect with Todd
Visit the show page
Get to know BrainStorm
Credits
Show direction: Debra Wilson
Show design: Kensie Smith
Show manager: Jenna Mollinet
44 min - Myth 2: It’s Not About Fewer Tickets—It’s About Better Ones
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 customers who are silently failing, loudly failing, and loudly succeeding
Why some support tickets are actually healthy signs of adoption, engagement, and expansion potential
How the first 90 days of the customer journey can strongly influence churn risk
Why users often do not ask “how” until they understand “why”
How training can sometimes lower confidence at first, not because it failed, but because it revealed new complexity and possibility
Why SaaS companies should stop treating training as a one-time event and start treating it as an ongoing process
How support, customer success, professional services, and education teams need to work together instead of operating separately
Why routing the right questions to the right team is critical for growth and customer outcomes
How companies can better measure success by analyzing what kinds of questions customers ask, when they ask them, and what those questions reveal
Contents
00:00 Introduction and Myth Setup
00:58 Why “reduce support tickets” is the wrong goal
03:24 Why executives fixate on support ticket volume
05:50 Why ticket quality matters more than quantity
06:49 Silently failing vs. loudly failing vs. loudly succeeding customers
08:19 “Users don’t ask how until they know why”
10:38 The kinds of support questions training should reduce
13:37 Why good training can actually increase valuable questions
17:19 Why the first 90 days matter so much
18:28 Common SaaS mistakes around training and adoption
23:12 Why training must be ongoing, not one-and-done
26:50 The three levels of customer questions
29:34 Why support and success teams often miss opportunities
31:03 Routing questions to the right team
36:49 Homework
Resources
Connect with Casey
Connect with Todd
Visit the show page
Get to know BrainStorm
Credits
Show direction: Debra Wilson
Show design: Kensie Smith
Show manager: Jenna Mollinet
38 min - 3 Misconceptions About Digital Customer Success with Kat Breeggemann, Founder @Katalyst CX
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 should not be limited to SMB accounts
How strong digital CS programs can support enterprise customers too, especially large groups of end users beyond the main point of contact
The idea of “seven times, seven ways” and why customers often need repeated communication across multiple formats
Which channels matter most in digital CS, including email, live events, video, in-app messaging, and education platforms
Why video is becoming one of the most effective ways to drive engagement, education, and adoption
How to think about measuring digital CS success through engagement, adoption, retention, renewals, and upgrades
The difference between a traditional CSM and a digital CS program manager, and why those roles may need distinct goals and metrics
Practical advice for building a digital strategy that balances technology, scale, and human connection
Contents
00:00 Introduction to Digital Customer Success
04:30 Misconceptions About Digital Customer Success
09:18 Best Practices for Digital Customer Success
14:22 Measuring Success in Digital Customer Success
18:56 The Role of Digital Customer Success in Enterprise Accounts
27:26 In-App Messaging: A Double-Edged Sword
36:49 The Power of Live Events in Customer Success
42:37 Homework Assignment: Embracing Video in Customer Success
Resources
Connect with Casey
Connect with Todd
Visit the show page
Get to know BrainStorm
Credits
Show direction: Debra Wilson
Show design: Kensie Smith
Show manager: Jenna Mollinet
51 min - Change Management in the Age of AI with Nicolette Stepakoff, VP of Change and Enablement @Eliza
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 implementation. The conversation also touches on the challenges of AI overload, the necessity of building strong partnerships in the SaaS space, and practical steps for organizations to take in order to effectively manage change and leverage AI tools.
Takeaways
Nicolette has a strong background in change management and enablement.
Change management was introduced as a pre-sales motion at Google.
Organizations often face resistance to change, even from change champions.
AI overload is a common issue in organizations today.
It's essential to align executive vision with user needs for AI tools.
Slow down to ensure that AI solutions are impactful and relevant.
Building a roadmap based on user workflows is crucial for AI adoption.
Strong executive sponsorship is key to overcoming resistance to change.
CSMs should focus on awareness and reinforcement of change management principles.
Inventorying workflows for automation can help organizations adapt to AI.
Contents
00:00 Introduction to Change Management in SaaS
02:37 The Importance of Change Management in Pre-Sales
07:06 Navigating AI Overload in Organizations
10:23 The Shift in Customer Needs and Expectations
13:56 Lessons from Microsoft’s Change Management Experience
16:36 The Role of Partners in Change Management
20:21 Building Healthy Relationships Between SaaS Vendors and Partners
23:31 Understanding End User Needs for Effective AI Implementation
27:57 Trends in Resistance to AI Adoption
31:22 Homework Assignment: Inventory Your Workflows
Connect with Nicolette here: [email protected]
Resources
Connect with Casey
Connect with Todd
Visit the show page
Get to know BrainStorm
Credits
Show direction: Debra Wilson
Show design: Kensie Smith
Show manager: Jenna Mollinet
37 min
About SaaS Therapy
From the publisher's feed
Get comfy. It's time for "SaaS Therapy," with industry veterans Todd Kirk and Casey Trujillo – the podcast for customer-facing teams in SaaS. Casey and Todd leverage their experience working between…
software vendors and their clients to help you master your SaaS customer relationships. They dig into the complexities of client relationships, offer expert insights, and share proven strategies for overcoming common challenges. It's not just a podcast—it's a masterclass in nurturing and enhancing your SaaS customer connections.