The Customer Success Playbook

Send us a textThe final episode of this transformative series tackles the ultimate challenge: scaling AI experiences without sacrificing empathy. Jake McKee reveals why most companies approach AI transformation backwards—focusing on tools instead of relationships, replacement instead of enhancement. This customer success playbook episode demonstrates how successful AI transformation mirrors the digital transformation of the past decade, requiring fundamental changes to business processes, not just technology adoption. McKee's framework for maintaining authentic human connections while scaling AI across enterprise environments provides practical guardrails for companies navigating the complex balance between efficiency and empathy. From addressing AI hallucinations transparently to designing trust through micro-moments, this conversation offers a roadmap for AI implementations that enhance rather than diminish human relationships.Detailed AnalysisMcKee's perspective on AI transformation represents a sophisticated understanding of organizational change management applied to emerging technology. His comparison to digital transformation provides crucial context—just as companies had to fundamentally rethink business processes when moving from analog to digital, AI transformation requires reimagining workflows, decision-making processes, and human-machine collaboration models.The conversation reveals critical insights about trust-building in AI systems, emphasizing that trust develops through consistent micro-moments rather than singular grand gestures. This mirrors human relationship dynamics and provides a practical framework for designing AI experiences that build confidence over time. McKee's examples of internal process failures—particularly the 13-screen system requiring hours of work before allowing saves—illustrate how poor experience design destroys trust regardless of underlying functionality.Perhaps most valuable is McKee's nuanced approach to AI transparency and hallucination management. Rather than attempting to eliminate AI limitations, he advocates for honest communication about system capabilities and uncertainties. This customer success playbook approach recognizes that users can develop healthy relationships with imperfect AI systems when expectations are properly set and limitations are communicated clearly.The discussion also addresses the critical challenge of scaling empathetic AI across large organizations. McKee's emphasis on relationship design over feature development provides a sustainable framework for maintaining human-centric experiences even as AI implementations grow in scope and complexity. His insights about contextual AI behavior—understanding when users need speed versus thoughtful interaction—offer practical guidance for enterprise AI strategy.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybookKevin's offeringPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.

Send us a textWhat happens when passionate customer feedback clashes with cold, hard data? Jake McKee tackles this age-old product dilemma with wisdom earned from years at Lego and building communities for Fortune 500 brands. This episode of the customer success playbook reveals why treating community building as relationship development—not just feedback collection—transforms how companies balance emotional customer input with analytical metrics. McKee's "everybody goes home happy" philosophy demonstrates how sustainable product decisions emerge when companies design mutually beneficial relationships rather than extracting value from user communities. From scale modeling to high-end fusion restaurants, this conversation weaves personal insights with professional strategies for community-driven product development.Detailed AnalysisMcKee's approach to resolving the tension between passionate customer feedback and data-driven metrics represents a sophisticated understanding of modern product development challenges. His framework moves beyond the traditional either/or mentality to reveal how qualitative community insights can actually strengthen quantitative analysis when properly interpreted through relationship context.The discussion illuminates critical flaws in conventional product development cycles, particularly the tendency to collect requirements upfront, disappear into development "black boxes" for months, then emerge with solutions disconnected from evolving customer needs. McKee's community-driven product development methodology keeps customer voices actively engaged throughout the development process, creating real-time feedback loops that prevent costly misalignments.Perhaps most valuable is McKee's perspective on starting small with community building. Rather than investing in expensive platforms and complex infrastructure, he advocates for beginning immediately with simple relationship-building activities—introducing customers to each other, facilitating peer connections, and treating community development as an ongoing relationship rather than a marketing project. This customer success playbook approach recognizes that authentic communities emerge from genuine value exchange, not sophisticated technology platforms.The conversation also explores the nuanced art of community participation, whether in branded platforms or external spaces like Reddit. McKee's guidance on "showing up" rather than "taking over" provides practical wisdom for companies looking to engage authentically with existing customer communities rather than disrupting established dynamics.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybookKevin's offeringPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.

Send us a textThe future of AI isn't just about technology—it's about relationships. Jake McKee, renowned as "the community guy," delivers a paradigm-shifting perspective on AI adoption that goes far beyond features and functionality. Rather than getting caught up in the technical capabilities, McKee advocates for designing the emotional connection between humans and AI systems. This customer success playbook episode reveals why the most successful AI implementations focus on relationship design, helping users feel comfortable whether they're interacting with a clearly identified robot or a humanistic assistant. McKee draws from his extensive experience at Lego and Fortune 500 companies to demonstrate how thoughtful AI experience design can transform user adoption and trust.Detailed AnalysisMcKee's revolutionary concept of "AI Experience Design" (AIX) represents a fundamental shift in how organizations should approach AI implementation. His core principle—"design the relationship, not the functionality"—challenges the prevailing rush to launch AI features without considering the human emotional experience. The discussion reveals critical insights about user psychology, particularly how people naturally anthropomorphize AI systems, using phrases like "please" and "thank you" even when they know they're communicating with machines.The conversation explores the delicate balance between AI enthusiasm and appropriateness, referencing recent challenges with overly enthusiastic AI responses. McKee emphasizes that successful AI relationships require the same nuanced understanding we apply to human interactions—matching energy levels, providing appropriate friction for creative processes, and recognizing when users need quick answers versus thoughtful collaboration.Perhaps most importantly, this customer success playbook demonstrates how AI transformation requires understanding context and purpose. A customer service agent dealing with frustrated callers needs rapid, efficient AI assistance, while a creative professional benefits from AI that provides "good friction"—intentional slowdowns that prompt deeper thinking rather than overwhelming users with instant responses. This strategic approach to AI experience design ensures technology serves human needs rather than creating additional complexity.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybookKevin's offeringPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.

Send us a textAI Friday delivers cutting-edge insights as John Huber reveals how artificial intelligence is transforming customer success operations. The conversation explores practical AI applications that are already delivering results, from conversation intelligence tools like Chorus for team coaching and customer context gathering, to emerging platforms like Sturdy that analyze unstructured data across email, Slack, and support tickets to identify churn risks and expansion opportunities. John challenges the overhyped notion that AI will replace CSMs, emphasizing instead how it amplifies human capabilities and enables more strategic engagement. The discussion culminates with an intriguing experiment: using custom GPTs for renewal pricing strategy that combines deal structure recommendations with benefit articulation. This customer success playbook episode demonstrates how forward-thinking CS leaders are leveraging AI to scale their impact while maintaining the human connections that drive customer loyalty.Detailed AnalysisThe episode showcases a mature understanding of AI implementation in customer success, moving beyond theoretical possibilities to practical applications with measurable business impact. John's progression from early adoption of Chorus to exploration of comprehensive platforms like Sturdy illustrates the rapid evolution of AI tools specifically designed for CS operations.The discussion of unstructured data analysis represents a significant leap forward in customer intelligence capabilities. Traditional CS platforms focus primarily on structured data points, but John's experience with AI-powered analysis of emails, support tickets, and communication channels opens new possibilities for early risk detection and opportunity identification. This capability addresses a long-standing challenge in customer success: the inability to systematically analyze the vast amount of unstructured communication that contains critical insights about customer health and growth potential.John's perspective on AI replacing CSMs demonstrates thoughtful leadership in an era of technological disruption. His emphasis on AI as an enabler rather than a replacement aligns with successful digital transformation strategies across industries. The human element remains crucial for building trust, navigating complex customer relationships, and making nuanced decisions that require emotional intelligence.The custom GPT experiment for renewal pricing represents the frontier of AI applications in CS operations. This use case demonstrates how AI can be trained on specific business contexts to provide both analytical recommendations and strategic guidance, potentially transforming how CS teams approach contract negotiations and renewal conversations.For CS leaders, this episode provides a roadmap for AI adoption that balances innovation with practical implementation, emphasizing tools that enhance rather than replace human capabilities.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybookPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.

Send us a textWednesday brings the burning question that divides CS and sales teams everywhere: who should own expansion revenue? John Huber tackles this contentious topic with nuanced insights drawn from his experience managing both dedicated CS-led expansion models and hybrid partnership approaches. Rather than offering a one-size-fits-all answer, John presents a thoughtful framework for determining the optimal structure based on deal complexity, sales cycle length, and organizational maturity. He shares specific examples of successful implementations, including a sophisticated model where CSMs handled straightforward upsells and renewals while account executives managed complex expansion opportunities. The discussion dives deep into compensation structures, forecasting methodologies, and the critical importance of clearly defining roles to avoid territorial conflicts. This customer success playbook episode provides practical guidance for leaders struggling to optimize their expansion strategy without sacrificing customer relationships.Detailed AnalysisThis episode addresses one of the most politically charged topics in revenue operations: expansion ownership. John's approach demonstrates sophisticated thinking about organizational design, moving beyond simple "CS versus Sales" debates to examine the underlying factors that should drive structural decisions.The hybrid model John describes represents an evolution in CS thinking, recognizing that different types of expansion opportunities require different skill sets and engagement approaches. His 70/30 compensation structure (70% quota-oriented, 30% experience-focused) within the variable component offers a practical framework for balancing commercial accountability with customer-centric behaviors.Particularly valuable is John's emphasis on forecasting churn and renewal business with the same rigor as new logo acquisition. His practice of conducting detailed risk assessments 4-5 months before fiscal year start demonstrates the proactive mindset required for successful renewal management. The recommendation to begin renewal conversations 12 months in advance challenges the reactive approach many organizations take to customer retention.The discussion also highlights the importance of cross-functional partnerships, especially between CS and finance teams, in developing accurate forecasting models. John's collaborative approach with his CFO shows how CS leaders can elevate their strategic influence by speaking the language of business operations.For revenue leaders, this episode provides a decision-making framework for expansion ownership that considers deal complexity, resource allocation, and organizational capabilities rather than defaulting to territorial thinking.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybookPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.

Send us a textSummaryThis episode kicks off a compelling three-part series featuring John Huber, founder of Customer Success Architects, who brings two decades of experience building CS functions across five different SaaS companies. The conversation centers on the fundamental question every growing business faces: how do you launch a customer success function that actually drives results? John shares his battle-tested approach, emphasizing the critical importance of aligning CS initiatives with company-wide strategic objectives rather than jumping straight into tactical execution. Through a fascinating case study involving a massive platform transformation for enterprise pharmaceutical and high-tech manufacturing clients, he demonstrates how proper alignment enabled a successful four-and-a-half-year migration from on-premise to cloud infrastructure without losing a single customer. This customer success playbook episode provides essential groundwork for any organization looking to build or rebuild their CS foundation.Detailed AnalysisThe discussion reveals several strategic insights that challenge conventional CS wisdom. Rather than immediately focusing on hiring CSMs or implementing technology platforms, John advocates for a "strategy-first" approach that ensures every CS initiative ladders up to broader business objectives. This methodology becomes particularly powerful when managing complex transformational projects, as evidenced by his experience migrating enterprise clients from legacy on-premise systems to modern cloud platforms.The episode highlights three critical success factors for new CS functions: strategic alignment with three-year company vision, cross-functional collaboration (especially with legal and finance teams), and allowing significantly more time than initially estimated for complex transitions. John's approach to contractual restructuring during platform migrations offers valuable lessons for companies navigating similar transformations, particularly the importance of providing financial incentives and flexible contract structures during transition periods.The conversation also underscores how customer success professionals must evolve beyond traditional support roles to become strategic business partners. John's team successfully positioned platform limitations as innovation opportunities, demonstrating the communication skills necessary to maintain customer relationships during potentially disruptive changes.For CS leaders and executives, this episode provides a practical framework for launching CS initiatives that deliver measurable business impact while maintaining strong customer relationships throughout complex organizational changes.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybookPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.

Send us a textThe Customer Success Playbook podcast wraps up its enlightening three-part series with Kristen Nolan of Interview Valet by exploring the delicate balance between technology and human connection. In this forward-thinking discussion, Kristen reveals how she leverages AI as a strategic tool while maintaining authentic relationships. From using AI to identify unique client differentiators to employing dictation for efficiency, this episode offers practical ways to harness technology without sacrificing the personal touch. Hosts Roman Trebon and Kevin Metzger guide a conversation that demonstrates how AI can enhance rather than replace meaningful connections in customer success.Detailed AnalysisAs AI continues to transform business operations, customer success professionals face a critical question: Can technology actually strengthen human relationships rather than diminish them? This episode provides a refreshingly balanced perspective that avoids both technological evangelism and fearful resistance.Kristen Nolan's approach to integrating AI into client relationships stands out for its pragmatism and strategic focus. Working at Interview Valet, where "relationships are the ultimate currency" serves as a core value, Kristen has developed a methodology that leverages AI as a starting point rather than an end solution. Her process of using tools like ChatGPT to identify a client's unique differentiators demonstrates how AI can enhance relationship-building by providing deeper insights that might otherwise remain undiscovered.What makes this discussion particularly valuable for the customer success playbook is the emphasis on maintaining authenticity while embracing technological efficiency. Kristen's guidance on viewing AI outputs as "a baseline" that requires human refinement offers a practical middle path for CS professionals concerned about sounding robotic or inauthentic in client communications. As she notes, "AI can't make up personal stories for you," highlighting the irreplaceable value of human experience in building genuine connections.The hosts share equally practical applications, with Roman revealing how he uses AI to improve the tone and client-centricity of his communications—not by blindly copying AI outputs, but by using them as a mirror to recognize when his natural communication style might come across as too abrupt. This application addresses one of the most common challenges in customer success: ensuring that necessary direct communications don't damage valuable relationships.For customer success teams looking to scale their operations without sacrificing quality, this episode provides a framework for thoughtful AI integration. The discussion moves beyond theoretical benefits to share tangible techniques like using ChatGPT projects to maintain context, leveraging dictation for efficiency, and using AI to help craft more concise communications. These practical tips demonstrate how technology can free up time for meaningful relationship-building rather than replacing it.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CuPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.

Send us a textThe Customer Success Playbook podcast delivers a thought-provoking exploration of confidence building in this captivating episode featuring Kristen Nolan of Interview Valet. Hosts Roman Trebon and Kevin Metzger guide a discussion that dives into overcoming self-doubt and imposter syndrome. Kristen shares her personal journey from questioning "who cares what I have to say?" to becoming a confident podcast guest who now coaches others. With refreshing honesty about her own struggles and triumphs, she reveals how facing fears head-on can lead to remarkable personal and professional growth.Detailed AnalysisBuilding confidence isn't just a personal development goal—it's a critical professional skill, especially in customer success roles where relationships and credibility are paramount. This episode tackles the universal challenge of silencing the inner critic that so often holds professionals back from reaching their full potential.Kristen Nolan's approach to confidence building centers on one powerful concept: taking action despite doubt. She candidly shares her own hesitation when first approached about being a podcast guest, revealing that her immediate reaction was, "Who cares what I have to say?" This transparent admission resonates because it reflects a common barrier many customer success professionals face—questioning their expertise or value.What makes Kristen's perspective particularly valuable for the customer success playbook is her emphasis on how facing fears creates a feedback loop of growth. By "ripping the bandaid off" with her first podcast appearance (which she admits was "pretty terrible"), she developed skills and insights that now help her better serve clients. This practical example demonstrates how pushing through discomfort directly enhances client relationship capabilities.The conversation takes an even more profound turn when Kristen addresses self-sabotage—identifying it as one of the most significant barriers to achievement. For customer success professionals, this insight is especially relevant, as hesitation in challenging client conversations or strategic recommendations can undermine effectiveness. Kristen's advice to visualize goals and map the path backward (her "Z to A thinking") offers a tactical approach to overcome this tendency.Perhaps most powerfully, the discussion draws a connection to broader life satisfaction, referencing the common deathbed regret of "not having the courage to live authentically." This reminder elevates the conversation beyond mere professional development to touch on how building confidence impacts overall life fulfillment—a holistic perspective that aligns perfectly with the integrated work-life approach many customer success professionals strive to achieve.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybookPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.

Send us a textIn this eye-opening episode of the Customer Success Playbook podcast, hosts Roman Trebon and Kevin Metzger welcome Kristen Nolan, Senior Client Account Manager at Interview Valet. As a military spouse, mother of three, and active community volunteer, Kristen shares her battle-tested strategies for managing a packed schedule. Her number one tip? Taking control of your calendar through intentional time blocking. Discover how this simple yet powerful technique helps Kristen juggle professional responsibilities while maintaining flexibility for life's unexpected moments and personal priorities.Detailed AnalysisEffective calendar management might be the most underrated skill in today's busy professional landscape. Kristen Nolan, who juggles multiple roles with impressive grace, offers a masterclass in time management that any customer success professional can immediately implement.Kristen's approach centers on what she calls "Z to A thinking" - a methodology where she identifies all weekly tasks first, then strategically schedules them on her calendar. This proactive stance ensures nothing falls through the cracks while maintaining flexibility to adapt when needed. As Kristen points out during the conversation, this intentionality creates space for both productivity and spontaneity - a balance many professionals struggle to achieve.For customer success professionals, Kristen's advice is particularly valuable. The demanding nature of client-facing roles often leads to reactive scheduling practices, where calendars become overrun with meetings, leaving little time for focused work. By implementing Kristen's time blocking technique, CS teams can carve out dedicated space for deep work while still maintaining client availability.What makes Kristen's approach stand out is her holistic perspective - combining personal and professional commitments in a single calendar system. This integrated view prevents the common pitfall of overbooking and creates realistic expectations for what can be accomplished each day. For customer success teams looking to improve efficiency without sacrificing client relationships, this balanced methodology offers a practical framework that can transform productivity.The customer success playbook continues to evolve, but fundamental skills like time management remain essential building blocks for professional excellence. Kristen's insights remind us that sometimes the simplest strategies yield the most powerful results.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybookPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.

Send us a textAs artificial intelligence promises to revolutionize project management, many professionals feel caught between excitement and overwhelm. In this AI Friday finale of their three-part series, Kevin Metzger and Roman Trebon explore with Elizabeth Harrin how to harness AI's power without losing the human touch. From security concerns to practical applications, Elizabeth delivers a refreshingly pragmatic approach to integrating AI into your project management toolkit without adding complexity to your already full plate.Detailed AnalysisThe episode begins with a reality check that resonates across industries: despite AI's massive potential, most project managers aren't using it – primarily due to security protocols and corporate restrictions. Elizabeth's survey findings reveal a gap between AI's promises and its practical adoption, setting the stage for a conversation about realistic implementation.Rather than pushing for revolutionary changes, Elizabeth advocates for evolution. Her advice? Start with AI functionality already embedded in your existing tools. Microsoft Copilot for meeting summaries, automated task suggestions, and workflow automation represent low-hanging fruit that sidesteps security concerns while delivering immediate value.Roman's observation about the basics strikes a chord – while early adopters race toward advanced AI applications, many professionals haven't even discovered time-saving fundamentals like automated meeting transcriptions. This highlights a crucial insight: successful AI adoption isn't about chasing the latest technology; it's about finding tools that solve real problems without creating new ones.Elizabeth's vision for AI focuses on eliminating repetitive work to create space for high-value activities like relationship building and strategic thinking. She paints a picture of AI as an assistant that handles data collection and analysis, freeing project managers to focus on what computers can't do – engage with people and build trust.The conversation takes a practical turn with specific examples. Imagine uploading a year's worth of monthly reports and asking AI to generate an annual summary – transforming hours of manual compilation into minutes of review. Or consider tools like ClickUp generating task lists from project ideas, or Tom's Planner and Nimble surfacing potential actions from historical data.Elizabeth's forward-looking perspective is particularly intriguing. She envisions AI analyzing historical performance data to predict deadline reliability – "Kevin has hit his deadlines 3% of the time" becomes actionable intelligence for better planning. While the percentage might sting, the insight enables smarter project management.The episode concludes with a powerful reminder: AI should support your work, not create more of it. For customer success professionals managing multiple projects, this means choosing tools that genuinely reduce cognitive load rather than adding another layer of complexity to master.Now you can interact with us directly by leaving a voice message at https://www.speakpipe.com/CustomerSuccessPlaybookPlease Like, Comment, Share and Subscribe. You can also find the CS Playbook Podcast:YouTube - @CustomerSuccessPlaybookPodcastTwitter - @CS_PlaybookYou can find Kevin at:Metzgerbusiness.com - Kevin's person web siteKevin Metzger on Linked In.You can find Roman at:Roman Trebon on Linked In.