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SaaS Therapy
By BrainStormBusiness
SaaS Therapy episodes
- The Path to Customer Success with Lincoln Murphy, VP of Customer Experience @ListKit
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
- Expansion is a natural progression for successful customers.
- Customer success is defined by the success of the customers themselves.
- Building an Ascension path can enhance customer journeys.
- Recognizing progress milestones can lead to expansion opportunities.
- Orchestrating customer experiences ahead of time is essential.
- Offering additional services at milestones can increase consumption.
- Understanding customer needs is crucial for business growth.
- A structured approach to customer success can drive revenue.
- Proactive engagement with customers fosters loyalty and retention.
- Customer journeys should be mapped to identify growth opportunities.
Contents
- 00:00 – Welcome to SaaS Therapy & Lincoln Murphy Intro
- 02:10 – Why Expansion Should Be a Natural Outcome of Customer Success
- 06:11 – Control the Controllables & Eating Customer Complexity with AI
- 14:26 – Who Should Lead Upsell: CS vs Direct Sales
- 17:50 – Enterprise vs SMB: Where to Start Your Expansion Motion
- 19:48 – “Upsell Will Ruin My Relationships” (And Why That’s Wrong)
- 23:49 – $20K AI Bill Story & The Danger of Wrong-Time Upsells
- 33:14 – Two Big Misconceptions About Expansion Programs
- 41:55 – Homework: Map Progress Milestones & Use AI to Accelerate Them
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
46 min - The Quality of Your Questions: CS Secrets from the Trenches with Todd Kirk and Casey Trujillo
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
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 - The Power of Compelling Calls to Action with Dallin Palmer, Cofounder @HALDA.AI
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
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 - Establishing New Success Metrics for Customer Education with Todd Kirk and Casey Trujillo
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
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
35 min - The Evolution of Customer Success Strategies with Dan Steinman, Director @ Colson Fellows
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
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 - Your Network is Your Net Worth with Carson Heady, Managing Director of Americas @ Microsoft
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
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
52 min - Meet Users Where They Are with Jillian Bejtlich, Sr. Manager of Community and Customer Marketing
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
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
46 min - The Science of Retention with Rachel Provan, Founder & CEO of Provan Sucess
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- Behavioral psychology plays a crucial role in customer success.
- Humans make decisions based on emotions, not just logic.
- Listening is key to understanding customer needs.
- Framing conversations can significantly impact engagement.
- Loss aversion affects customer retention decisions.
- Tailor your message to different customer personas.
- Invisible implications can influence customer decisions.
- Sales mistakes often stem from a lack of empathy.
- Small actions can lead to significant improvements in sales.
- Continuous learning and adaptation are essential in customer success.
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
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
45 min - Unlocking Productivity with Outlook with Todd Kirk and Casey Trujillo
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
- Celebrate your successes to motivate your audience.
- Focus on creating excitement in training sessions.
- Use micro learnings to engage users effectively.
- Understand the importance of change management.
- Empathize with users to ease transitions.
- Create 'wow' moments to enhance learning.
- Utilize new features in software for productivity.
- Encourage user participation in training.
- Reinforce learning to combat the forgetting curve.
- Evaluate your training methods for effectiveness.
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
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
32 min - Turning Problems Into Solutions with Ashley DeKerlegand, Director of CE and CX Enablement @ QuickBase
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
- Action Mapping focuses on behavior change rather than just knowledge.
- Measurable goals are essential for effective training.
- Collaboration across teams enhances the learning process.
- Empathy is crucial in understanding learner challenges.
- Transforming obstacles into opportunities is key to success.
- Real-life applications of Action Mapping can drive significant results.
- Avoid information dumps; focus on observable actions.
- Executive sponsorship is vital for implementing new frameworks.
- Understanding the 'why' behind actions leads to better outcomes.
- Action Mapping can be applied in various contexts, including personal life.
Contents
00:00 Intro
2:34 Action Mapping Framework Explained
5:42 Real-World Applications & Challenges10:36 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
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
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.