Tag: product management leadership

  • Inside Zipline’s Wild Pivot: My Take on Hiring Heat-Seekers and Scaling to 5,000 Hospitals

    Inside Zipline’s Wild Pivot: My Take on Hiring Heat-Seekers and Scaling to 5,000 Hospitals

    I’m consistently drawn to stories where product strategy and operational grit collide to change real lives. Zipline, the world’s largest commercial autonomous delivery system, is one of those rare cases. Serving 5,000 hospitals across multiple countries and saving an estimated 17,000 lives per year, it embodies the kind of mission-driven execution I try to model in product management. The arc—from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown—offers some of the clearest lessons I’ve seen on hiring, leadership, and product-market fit under extreme constraints.

    One principle that immediately resonated with me: why Zipline doesn’t hire for experience. The idea behind “Why Zipline hires teenagers over PhDs” isn’t a dismissal of expertise; it’s a commitment to learning velocity, ownership, and unteachable hunger. The best startup employees, as described here, are “heat-seeking missiles for pain”—people who chase the hardest problems, not the shiniest projects. In my org, I look for the same signal: candidates who can move from ambiguity to action, who find the bottleneck without being asked, and who care more about outcomes than optics.

    I also appreciated the unapologetic stance that “blind references are a non-negotiable.” In high-stakes builds—especially in regulated or safety-critical categories—the cost of a mis-hire compounds. I routinely validate for two traits during references: intellectual humility and accountability. “Can candidates admit when they screwed up?” is a powerful filter. If someone can’t name a hard mistake and how they specifically changed as a result, they’re unlikely to scale with the organization.

    Equally important is clarity about who not to hire. The employees Zipline doesn’t want are those who optimize for status, process theater, or low-friction work. In practice, that means pressure-testing for problem-finding, not just problem-solving. I often design interviews around messy, cross-functional constraints (regulatory, operational, and financial) to see who can integrate tradeoffs, not just ideate features. That’s how we build empowered product teams that ship consequential outcomes, not outputs.

    There’s a reference to “Zipline’s secret leadership playbook,” and while the specifics remain private, the spirit is unmistakable: first principles decision making, ruthless focus, and a culture that rewards radical responsibility. Translating that to my product organization, I emphasize five behaviors: orient to the mission under uncertainty, run fast but close the loop with data, communicate constraints early and often, own the long tail of consequences (especially in safety and reliability), and scale judgment by teaching the why, not just the what. That blend of clarity and autonomy is the backbone of product management leadership at any growth stage.

    On the other side of the culture coin is “Why you should always fire quickly” and “The brutal firing advice that shaped Keller’s leadership.” I’ve learned (sometimes the hard way) that slow decisions erode trust and team velocity. Moving quickly doesn’t mean being harsh; it means being fair, explicit, and humane—tight feedback loops, role clarity, and decisive action when the gap persists. If your bar is clear and your coaching is consistent, acting fast protects both the mission and the team’s energy.

    Strategically, the origin story reads like a masterclass in choosing the right problem. The team moved “from toy robots to drone delivery: Zipline’s pivot,” then partnered deeply with Rwanda, where “How Rwanda’s health minister changed everything” is a pivotal moment. It wasn’t a linear climb—”How Zipline almost died – twice” and “Why Zipline’s launch was a ‘complete disaster’” underline a tough truth: breakthrough products rarely arrive fully formed. What matters is the operating cadence that turns early chaos into repeatable reliability—especially when the stakes are measured in minutes and lives.

    Scaling from 1 hospital to 5000 required more than product brilliance; it demanded systems thinking across logistics, compliance, safety, and community trust. That’s stakeholder management at its highest level. The product lessons are durable: anchor on outcomes, not artifacts; build reliability as a feature; and practice founder-led GTM where your credibility is on the line with customers and regulators. This is where first principles decision making beats benchmarking—particularly in novel categories where there are no playbooks to copy.

    There’s also a hard-nosed operational takeaway in “The 10x hardware cost rule every founder should know.” My read: assume total cost of ownership will balloon once you account for manufacturing variability, support, redundancy, maintenance, and compliance. In product strategy, I treat those multipliers as design inputs, not afterthoughts. If the unit economics can’t survive these realities, the idea isn’t ready—no matter how elegant the prototype looks in a lab.

    Across all of this, a few product management patterns stand out for me: build teams around outcomes vs output OKRs; hire for slope, not just intercept; make continuous discovery routine with real users (in this case, clinicians and health systems); and treat operational excellence as a product surface. When a mission is this consequential, culture becomes a safety system—and every leadership decision compounds into either speed with quality or speed with regret.

    For leaders building in complex domains, this journey is a blueprint: pick problems that matter, hire “heat-seeking missiles for pain,” keep blind references non-negotiable, lead with first principles, and scale with responsibility. Do that well and even a “complete disaster” launch can become the inflection point of a category-defining company that flies 135 million autonomous miles and saves 17,000 lives per year.


    Book a consult png image
  • Mastering NRR: How Great Customer Success Teams Drive Expansion, Crush Churn, and Scale PLG

    Net Recurring Revenue (NRR) is the cleanest truth-teller in my operating system. When I review NRR, I’m not just looking at whether we renewed accounts—I’m assessing whether our product and customer success motions are compounding revenue from our existing customers. Put simply: good CS teams protect revenue; great CS teams grow it through adoption, expansion, and durable retention.

    Here’s how I frame NRR with my teams: it reflects revenue from our current customers after expansion, downgrades, and churn. If it’s at or above 100%, the installed base is self-sustaining; if it’s materially above 100%, the base is funding growth without net-new sales. That’s the holy grail for product-led growth and the benchmark I use to separate good from great.

    At HighLevel, I’ve learned that you can’t “wish” your way to high NRR. You operationalize it. We align incentives, dashboards, and rituals so everyone—from PMs to CSMs to Solutions Engineering—owns the same outcome. Our “QBRs vs OKRs” discussions anchor on NRR drivers: activation rates, time-to-value, feature adoption depth, and expansion readiness. Those leading indicators tell me where we’ll land on lagging revenue results.

    The best Customer Success teams operate like product teams. They use behavioral analytics and retention analysis to segment customers by use case and maturity, then design journey mapping to move each segment from first value to habitual value. They proactively reduce risk while creating clear expansion paths—new seats, premium features, or higher-tier plans—based on real product usage, not guesswork.

    Onboarding is where great NRR trajectories begin. I focus on compressing time-to-first-value and time-to-second-value because those moments create the habit loops that underpin renewal and expansion. In practice, that means targeted in-app guides, contextual product tours, and nudges that drive user activation across the “sticky” features that correlate most with long-term retention.

    To make this scalable, we blend human and product-led touchpoints. CSMs run outcome-based playbooks, while the product experience handles education and reinforcement at scale. When usage signals an expansion opportunity—say, a team consistently bumps into plan limits—we generate a product-qualified expansion lead and equip the CSM with the exact value storyline and proof points to close it.

    Increase revenue, cut costs, and reduce risk with Pendo’s Software Experience Management platform. Optimize the entire software experience to drive adoption and improve engagement.

    I’ve seen this playbook move the needle. After instrumenting our key workflows and deploying targeted in-app guidance, we watched adoption of our highest-retaining features climb, risk flags surface earlier, and expansion conversations become far more data-driven. We didn’t chase shiny objects; we built a reliable pipeline of retained and expanded revenue directly from product usage.

    If you’re aiming to level up NRR, start with a crisp blueprint: define the critical events that predict renewal and expansion; set activation milestones per segment; deploy in-app guides and product tours to remove friction; give CSMs a single-pane view of risk and readiness; and review NRR weekly with the same seriousness you apply to new ARR. Consistency beats intensity here.

    Finally, keep the narrative simple. Your leadership story isn’t “we shipped features,” it’s “we created customer outcomes.” Tie every CS and product initiative back to NRR drivers—and make the wins visible. When teams see the direct line from great onboarding and adoption to measurable expansion, they naturally operate like a unified, product-led growth engine.

    NRR rewards rigor. Treat it as the top-line health metric for your installed base, make the software do more of the teaching, and empower CS to coach to outcomes. Do that well, and you won’t just separate the good from the great—you’ll build a compounding machine.


    Inspired by this post on Pendo – Best Practices.


    Book a consult png image
  • Kill Your Darlings: Why I Sunset ‘Successful’ Products to Fuel Real Portfolio Growth

    Kill Your Darlings: Why I Sunset ‘Successful’ Products to Fuel Real Portfolio Growth

    There’s a moment in every product leader’s career when the bravest decision isn’t to build—it’s to stop. That’s why the “Kill Your Darlings” theme resonated so strongly with me. In this episode of All Things Product, Teresa Torres and Petra Wille dig into the courage and craft it takes to sunset products that look successful on the surface yet quietly block your path to meaningful growth. As someone accountable for portfolio outcomes, I’ve learned that disciplined endings are often the catalyst for exceptional beginnings.

    Listen to this episode on: Spotify | Apple Podcasts

    The heart of the conversation is that uncomfortable middle ground between obvious failure and runaway success: products that are profitable, loved by customers, but fundamentally flatlining. Teresa shares candid stories from her own business, including a decision to cut 40% of revenue on purpose. I’ve been there—choosing to retire a “working… kind of” product to free up discovery capacity felt risky in the moment, but it created the focus we needed for durable growth.

    Here’s the trap: some traction can be more dangerous than no traction at all. Early fans are not the same as durable product–market fit, and “stable but not growing” can lull leaders into maintaining instead of learning. Every hour of design, engineering, and go-to-market attention that props up a flatlining product is an hour not invested in the next breakthrough—an opportunity cost that rarely shows up on a dashboard, yet compounds month after month.

    From a portfolio perspective, this is continuous discovery in action. If we want empowered product teams to tackle meaningful outcomes, we have to protect their capacity from zombie work. That means setting clear thresholds for when we double down, shift strategies, or sunset—before attachment and inertia take over. When I’ve institutionalized this discipline, our throughput of high-quality bets increased, and our confidence in what not to do became a strategic advantage.

    Organization design can make sunsetting harder than it needs to be. Dedicated, long-lived teams are fantastic for compounding capability, but they also create emotional and structural ties to specific products. Petra’s point lands: leaders need explicit sunsetting conversations and a portfolio decision-making cadence that sits one level above teams. In my org, we treat sunsetting as a strategic reallocation—not a verdict on a team’s talent—so people are celebrated for learning, not punished for outcomes outside their control.

    Killing profitable products can be the right strategic move when the growth ceiling is clear and the opportunity cost is high. I’ve chosen to “burn the ships (on purpose)” more than once—retiring add-ons that generated reliable revenue but diluted our value proposition and spread discovery thin. Yes, it stings in the quarter you do it. But it’s astonishing how quickly focus restores momentum when you create intentional space for what’s next.

    Practically speaking, I make sunsetting easier and less traumatic by operationalizing it: Regular portfolio reviews focused on outcomes and opportunity cost; a visible “sunsetting” column so everyone sees what’s on the table; the Horizon (H1 / H2 / H3) model to balance core, adjacent, and transformational bets; and making portfolio decisions one level above teams to avoid local optimizations. Add explicit exit criteria and success metrics for endings, the same way we set entry criteria for new bets.

    Another theme I appreciated is designing for the right customers. Teresa highlights intentionally limiting access and pricing to work with customers who show agency and commitment. I’ve applied the same principle: when we’re clear about who we serve and who we don’t, our product–market signal sharpens, churn narratives simplify, and roadmaps get crisper. Focus is a growth strategy.

    If you’re leading a product portfolio, running discovery, or wrestling with a product that “works… kind of,” this conversation is permission to act. Product–market fit isn’t binary, and mediocre success can be the most dangerous place to stay. Sunsetting is a portfolio decision, not a team failure; teams shouldn’t be punished for reaching the end of a product’s natural lifecycle. If experimentation isn’t in your DNA, killing products will always feel traumatic—so make space for it intentionally, not passively.

    Key moments and themes worth bookmarking: 00:00 – Why “kill your darlings” matters; 04:30 – The dangerous middle ground; 09:30 – The opportunity cost of “okay” products; 14:30 – Sunsetting in product organizations; 19:00 – Real examples of killing revenue streams; 28:00 – Designing for the right customers; 33:30 – Burn the ships (on purpose); 38:00 – Making sunsetting easier with Regular portfolio reviews, a visible “sunsetting” column, the Horizon (H1 / H2 / H3) model, and making portfolio decisions one level above teams; 46:00 – Normalizing product lifecycles.

    Resources & Links:

    Follow Teresa Torres: https://ProductTalk.org

    Follow Petra Wille: https://Petra-Wille.com

    Mentioned in this episode:

    Ways to Work with Petra Wille

    Product at Heart

    CDH Membership by Teresa Torres

    Product Talk by Teresa

    Product Talk Academy by Teresa

    Enduring Ideas: The three horizons of growth

    Join the Conversation:

    Have thoughts on this episode? Leave a comment below.

    Full Transcript

    Full transcripts are only available for paid subscribers.


    Inspired by this post on Product Talk.


    Book a consult png image
  • Turn Support Wins into a Company-Wide AI Blueprint for Consistent, End-to-End CX

    Turn Support Wins into a Company-Wide AI Blueprint for Consistent, End-to-End CX

    Building a great end-to-end customer experience with AI means going beyond support, and I’ve seen firsthand how transformative that shift can be when we treat every interaction as part of one cohesive journey.

    Every customer touchpoint, from the first sales conversation through to post-sales support and success, is an opportunity to get it right. Other teams are now turning to AI to transform how they show up for customers, and support, which led the way, has already written the blueprint. In my role, I focus on making that blueprint actionable across the entire lifecycle.

    In The 2026 Customer Service Transformation Report, it’s clear most businesses are thinking about what’s next, with more than half planning to scale AI to other departments. Interestingly, they often cite their early success with AI in support as motivation for the move. This makes support teams uniquely positioned to help lead the transition, a strategic role unimaginable just two years ago.

    In this piece, I share how teams are introducing AI to other parts of the business, how to think about this expansion effort, and the new opportunities it creates for support leaders who want to drive a unified customer experience.

    Support was the first proving ground for AI, and our research suggests that businesses are now planning to expand its use to other areas based on the results it’s yielded so far. Fifty-two percent of respondents said that their organizations are actively planning to scale AI to other departments in 2026.

    What will this look like? Leading companies are already finding out.

    Survey chart showing why organizations expand AI beyond support: success with AI in support 57%, unified customer experience 49%, scaling other functions without added headcount 33%, and cross-department requests 31%.
    Wins in support are setting the pace for company-wide AI. Survey results rank the drivers: proven success in support (57%), the push for a unified customer experience (49%), scaling other functions without more headcount (33%), and cross-department demand (31%).

    My favorite example is WHOOP, the fitness wearables company. They offer a premium product which makes their sales conversations more consultative than transactional. Customers want to know “Which membership is right for me?” or “How often do I need to charge my WHOOP?” According to Emily Shirley, Business Manager for Growth Product at WHOOP, if someone chatted with the inside sales team, they were twice as likely to convert, but they didn’t have enough reps to respond to incoming queries fast enough. Customers could wait more than 10 hours for a reply.

    With a big product launch on the line and an anticipated spike in prospective customer conversations, their three-person team needed help. So they deployed Fin to the "Join" page, the final step before purchase.

    With Fin resolving 84% of inbound questions, the sales team was able to focus on high-value leads. Together, they drove a 130% increase in attributable sales. The team is now exploring ways to expand Fin beyond FAQs, focusing on personalised conversation flows, multi-product recommendations, and richer data capture. As Emily says: “There are so many parts of the buyer journey where this applies. We’ve only scratched the surface.”

    It’s clear there’s a desire to push AI to other parts of the customer lifecycle, but there is a risk hidden in this expansion. If sales, customer success, and other departments all launch their own Agent, each operating in isolation, you can end up fragmenting the very thing our research says teams want to create. The second-most cited reason for pushing AI beyond support: desire for a unified customer experience.

    Without shared context, each handoff becomes a source of friction where customers could receive inconsistent answers or be asked to repeat information. I’ve watched even well-intentioned AI rollouts struggle here—great local wins, but an overall journey that feels disjointed.

    Diagram of an AI support blueprint showing roles (SDR, CSM, Sales, Shopping Assistant, Support Rep, Custom) stacked above layers for Goals, Memory & User Context, Business Knowledge, and Interoperability.
    A translucent UI visual maps a support-led AI blueprint that scales across the business—from SDR and sales to custom assistants—anchored by layers for goals, memory and user context, business knowledge, and interoperability.

    The opportunity (and the challenge) is to keep the customer at the center. Instead of department-specific Agents that operate independently, we must strive for cohesion. That means shared memory, consistent governance, and connected AI workflows that respect the customer’s history and intent across channels.

    This is the future I’m building toward: solutions like Fin becoming a “Customer Agent,” capable of handling the entire customer experience. This will mean Fin can function in many roles, supported by a memory that grows with the customer over time and deep knowledge of the business, creating a seamless experience for every interaction. In practice, that’s agentic AI designed to collaborate across teams, systems, and journeys—without losing context.

    Pushing AI into new parts of the business requires someone to own the process. And for many organizations, that’s the support team. Nearly a third of respondents (32%) confirmed their customer service teams are leading their business' AI transformation strategy.

    This presents a real opportunity for support teams to shape the future of customer experience. Instead of each function reinventing the wheel, support can act as a center of excellence, defining shared standards, guardrails, and operating practices that drive performance.

    “You already manage the most complex, high-volume customer interactions; you have rich data on customer needs and behavior; and you know how Agents perform in the real world. Those insights will be invaluable as AI scales across your business.”

    Neon green hero graphic reading 'The 2026 Customer Service Transformation Report', with subhead 'The AI deployment gap is widening' and a black 'Get the report' button over a bar-chart pattern.
    Leaders are racing ahead with real AI in support. Explore the 2026 Customer Service Transformation Report to see where deployment is stalling, benchmark your team, and get practical steps to scale automation that delights.

    In my organization, when we extended AI from support into sales, we deliberately brought our conversation design expertise, Agent Analytics, and governance models along with it. One team owns the orchestration, memory strategy, and CRM integration so a customer can start with a sales question and end up with a support one—without ever feeling a seam. That continuity is where journey mapping meets product strategy and turns into measurable outcomes.

    As Agents like Fin expand their capabilities and move into new areas, I expect many customer service leaders will see their roles expand to include AI implementation across the customer journey. It’s a natural progression for product management leadership in support: owning the experience, the data, and the operating model.

    Achieving perfect customer experience is AI’s biggest promise. But in order to get there, teams need to be smart about the solutions they deploy. A unified Customer Agent capable of handling the entire journey end-to-end will have a significant advantage, delivering consistent, context-aware experiences across every interaction.

    The Customer Agent future is being built right now, and it’s starting with the team pioneering AI transformation from the very beginning: support. For leaders in these organizations, this is a rare opportunity to shape how customer relationships will be built and maintained in the AI era.

    If you’d like to dig deeper into the data and benchmarks guiding these decisions, download The 2026 Customer Service Transformation Report.


    Inspired by this post on The Intercom Blog.


    Book a consult png image
  • Prevent Strategy Drift: AI that flags ‘merge conflicts’ in product plans before a quarter derails

    Prevent Strategy Drift: AI that flags ‘merge conflicts’ in product plans before a quarter derails

    "What if an AI could spot the moment two product teams start pulling in opposite directions — before it derails a quarter?" That question hooked me, because I’ve lived through the costly fallout of subtle misalignments that only surface at the end of a sprint—or worse, during quarterly business reviews.

    I recently dug into an episode of Just Now Possible featuring Matthias and Charlotte Kleverud, co-founders of Momental. Their vision for "GitHub for product management" hits a nerve in the best possible way: find "merge conflicts" in strategy, not code, and do it early enough to save execution time, trust, and outcomes.

    Here’s the core: Momental ingests documents, meeting transcripts, and voice recordings across an organization, then uses AI agents to map them into a structured context layer—a set of interconnected trees covering goals, decisions, learnings, and who's doing what. When it finds a conflict—say, one team betting on retention while another is prioritizing conversion—it surfaces the misalignment for humans to resolve, just like a merge conflict in code. That framing is both familiar (for anyone who’s shipped software) and powerful (for anyone who’s scaled product strategy across multiple teams).

    Their journey tracks with what many of us have learned the hard way. "Starting in 2022 with DaVinci 002 and learning that the market wasn't ready for AI-assisted product thinking" pushed them toward experiments with agent teams. "The origin story: building a team of AI agents in 2024, only to discover agents hit the same alignment problems as humans" is exactly the kind of meta-lesson I’d expect when you scale autonomy without shared context. The breakthrough was an "OODA-loop-driven document processing agent" that continuously curates a living knowledge graph rather than relying on static prompts or brittle pipelines.

    One model that stood out was "The product chain: signals → learnings → decisions → principles, and how AI maps it." That is the backbone of healthy product thinking. When this chain is explicit and inspectable, you can trace why a team chose Path A over Path B—and detect when new signals should invalidate old decisions. I’ve seen this accelerate continuous discovery and improve executive decision hygiene.

    I also appreciated the organizational modeling: "Three trees that model an organization: the product tree (OKRs to epics), the wisdom tree (decisions and their reasoning), and the people/time tree." This maps cleanly to how we run quarterly planning at scale—tying outcomes to work, preserving rationale, and grounding ownership and timelines. With that structure, "How conflicts are detected, auto-resolved, or escalated to humans with merge options" becomes a pragmatic workflow, not a theoretical AI demo.

    On the technical front, they’re blunt about limits: "Why traditional chunking and RAG breaks down at scale and what Momental does instead." Anyone who’s tried to stitch strategy from ad hoc notes knows that naive retrieval won’t cut it. You need durable context boundaries, rich metadata, and graph-aware reasoning. Which brings me to one of my non-negotiables: "Why metadata—who said it, when, and in what context—is critical to preventing hallucinations." In my world, we treat provenance like test coverage—you can’t ship without it.

    Process-wise, the product philosophy resonated: "How a document processing agent uses OODA-loop thinking to extract and connect context across documents" reinforces the need for short feedback cycles, explicit hypotheses, and continuous refactoring of knowledge. Pair that with "The self-improving agent: collecting user feedback weekly and rewriting its own prompts" and you’ve got a blueprint for eval-driven development that keeps the system honest over time.

    Their UI choices also mirror a pattern I’ve adopted: "Moving from chat-first to UI-first to proactive agents as an AI product design pattern." Chat can feel magical, but alignment work benefits from concrete artifacts—trees, timelines, driver trees, and opportunity solution trees—so people can reason together. Then, let proactive agents watch for drift and nudge teams before the cost of change spikes.

    Two broader themes are worth calling out. First, "Specialized tools win" when the problem is deep, cross-functional context like product strategy. General-purpose chatbots struggle here; domain-specific models with strong information architecture have the edge. Second, product culture matters: "Discovery Versus Vibe Coding" is not just a catchy contrast—it’s a reminder that disciplined discovery beats intuition theater when stakes are high.

    As for the roadmap, I’m encouraged by their "Design partner strategy and what's next for Momental's public launch." Early design partners are where you validate signal quality, precision of conflict detection, and the ergonomics of human-in-the-loop resolution. I’m especially curious how this intersects with LLMs for product managers, outcomes vs output OKRs, and product roadmapping and sprint planning in large portfolios.

    Finally, a nod to the broader ecosystem. The conversation touched on "Claude Code" and a shift "Beyond documents and vectors" that many of us are living through—toward retrieval-first pipelines that respect context windows, stronger governance, and measurable improvements in decision quality. If you care about AI Strategy for empowered product teams, this is a space to watch—and to pilot.

    Bottom line: If you’ve ever wished you could prevent strategy drift before it shows up in your dashboards, this "GitHub for product management" approach is worth your attention. Make the chain of signals, learnings, decisions, and principles explicit. Keep humans in the loop for the hard calls. And let proactive, agentic AI do what it does best: flag misalignments early, so your teams can move fast together.


    Inspired by this post on Product Talk.


    Book a consult png image
  • From Chaos to Clarity: My Proven Playbook to Scale an Analytics Taxonomy That Sticks

    From Chaos to Clarity: My Proven Playbook to Scale an Analytics Taxonomy That Sticks

    I’ve stepped into too many product reviews where teams argued over numbers that should have been obvious. Three names for the same “signup” event, properties scattered across tools, and no shared definitions—classic analytics chaos. As VP of Product Management at HighLevel, I’ve learned that scaling an analytics taxonomy isn’t just a data exercise; it’s a leadership mandate that unlocks decision velocity, alignment, and confident product bets.

    Learn best practices our professional services team has compiled in helping customers move from scattered events to a scalable, user-friendly data structure.

    Why does this matter so much? A robust taxonomy powers a unified analytics platform across Amplitude analytics, Pendo, and our CRM stack, reduces rework, and strengthens data governance. When events are clear and consistent, product-led growth accelerates: onboarding becomes measurable, activation is trackable, and retention analysis turns into a weekly ritual rather than a quarterly scramble.

    I always start with outcomes, not events. We define a North Star metric and use driver trees to map how user behaviors ladder up to that outcome. Then we ground the plan in journey mapping: what signals mark activation, aha moments, and long-term engagement? This ensures our taxonomy mirrors real user intent, not just engineering convenience.

    Next comes naming conventions and structure. We standardize on a readable, durable pattern (for example, actor_action_object), apply consistent property naming, and document required vs. optional properties. We version events deliberately, so we can evolve without breaking dashboards. Most importantly, we align events to product strategy—tracking less, but better.

    Governance makes it scale. We establish a clear DRI for the tracking plan, a lightweight review process for changes, and a schema registry that serves as the single source of truth. Privacy-by-design is non-negotiable: we treat sensitive fields deliberately and audit access. Observability closes the loop—schema validations and alerts catch drift before it confuses teams.

    Tooling and process turn good intentions into muscle memory. We keep the tracking plan “as code” in a repository, run CI/CD checks to validate events, and use feature flags to roll out new instrumentation safely. Pendo helps us annotate in-app experiences, while Amplitude provides the exploratory lens for cohorts, funnels, and retention. Together, these systems reduce guesswork and speed up discovery.

    Migrations are where many teams stall, so I de-risk them with a clear, time-boxed plan. We audit the current event surface, map scattered events to the new taxonomy, and deprecate duplicates with guardrails. We communicate changes broadly, provide easy-to-scan documentation, and pair enablement sessions with hands-on examples from live dashboards. The goal is confidence, not just compliance.

    We measure success like a product. Are we answering critical questions faster? Are duplicate events trending down? Are activation and retention questions easy to answer in under five minutes? When the taxonomy is working, stakeholders stop asking, “Do we trust this?” and start asking, “What should we build next?”

    One of the most rewarding shifts I’ve seen: product trios moving from ad-hoc analyses to repeatable, weekly rituals. With crisp definitions, onboarding flows become testable, PLG motions are predictable, and leadership reviews focus on outcomes, not definitions. That’s the moment analytics transforms from a cost center into a growth engine.

    If you’re staring at a wall of scattered events, start small: clarify outcomes, align your journey map, set conventions, and ship a minimum viable taxonomy to one critical flow. Iterate quickly. The compounding payoff—clarity, speed, and trust—will be obvious to every team you partner with.

    When we do this well, analytics becomes a strategic asset. Our teams spend less time reconciling numbers and more time building what matters. That’s the real meaning of moving from chaos to clarity.


    Inspired by this post on Amplitude – Best Practices.


    Book a consult png image
  • March CDH Book Club: Master Experience Mapping to Align Teams and Accelerate Discovery

    March CDH Book Club: Master Experience Mapping to Align Teams and Accelerate Discovery

    I’m thrilled to invite you to our March session of the CDH Book Club. Continuous Discovery Habits turns five this year. And to celebrate we are reading the book together. I’ve seen firsthand—leading product trios and empowered product teams—that sharpening our discovery habits is the fastest way to better outcomes vs output OKRs, tighter team alignment, and more confident product strategy.

    Each month, I am releasing an in-depth reading guide that includes:

    The chapters we will be reading

    A preview of the most important concepts we'll be learning about

    Short videos you can share with friends and colleagues to help spread the ideas

    Individual and team discussion questions to help you absorb and engage with the reading

    Team exercises to help you put the ideas into practice

    Additional reading to help you go deeper on the core ideas

    We’ll be discussing each month’s reading in the comment section and we’ll gather quarterly to discuss on a live call. I’ll be there to trade notes, compare experience maps, and share what’s working across product discovery practices.

    Joining late? No problem. I monitor the comments on each reading guide throughout the year. Start with the current month or go back to January—whatever works for you. You can ask for help, share what’s working, and connect with other readers at any point.

    If you want to participate, grab a copy of the book (or dig up your old copy), share the "Spread the Love" videos, reserve some time to do the team exercises, and register for the community sessions. Let’s do this!

    This Month’s Reading

    Chapters:

    Chapter 4: Visualizing What You Already Know

    Estimated reading time: ~14 minutes

    This chapter will introduce you to:

    Why starting individually—rather than as a group—is the fastest path to unlocking your team’s collective intelligence

    How drawing (even badly) forces you to get specific in ways that words never will

    The strategic choice of setting your experience map’s scope—too narrow and you miss opportunities, too broad and you lose focus

    How diverse perspectives become your team’s secret weapon when you know how to synthesize them

    Why your first experience map isn’t truth—it’s a hypothesis you’ll test and evolve with every customer conversation

    Need a copy? Grab the book.

    Share the Love with Friends and Colleagues

    We learn best in community. Use the following short videos to share the key concepts from this chapter with friends and colleagues. Invite them to participate in the book club with you. In my teams, these quick hits help us align faster before we co-create an experience map or opportunity solution tree.

    Visualize your thinking – To bring others along

    Unlock team alignment – With visualizations

    Reflect & Discuss What You Read

    When we reflect and discuss what we read, we absorb more of the material. It helps us put what we learn into practice. Don’t skip this step. In my own practice, the real unlock came when I treated mapping as a living artifact that shapes customer interviews, not a one-off deliverable.

    Most of us believe we work collaboratively, but we’ve never truly experienced what it means to build shared understanding from diverse perspectives. This chapter challenges you to get uncomfortable—to draw when you’d rather talk, to work alone before working together, and to see your maps as living documents rather than one-time deliverables.

    Individual Reflection

    Think about the last time your team tried to align on what you know about your customers. Did everyone start by creating their own perspective first, or did you jump straight into a group discussion? What happened as a result?

    When was the last time you drew something at work? What stops you from using drawing as a thinking tool—is it discomfort with your drawing skills, lack of time, or something else?

    Look at your current work. If you were to create an experience map right now, what scope would you choose? How does your desired outcome help you determine what to include and what to leave out?

    Team Discussion

    As a trio, each person should identify one unique perspective they bring to your team’s understanding of your customer. How might these different viewpoints create blind spots if you only relied on one person’s view?

    When your team disagrees about what customers need or want, how do you typically resolve it? Do you debate until someone wins, defer to the most senior person, or test your different hypotheses?

    Does your team have a current experience map? If so, when was the last time you updated it based on what you’re learning from customers? If not, what’s preventing you from creating one?

    Put It Into Practice

    Understanding why experience maps matter is different from actually creating one that drives your discovery work. These exercises will help you practice the discipline of starting individually, synthesizing diverse perspectives, and using your map to guide customer conversations. My suggestion: timebox, embrace imperfect drawings, and let the artifact lead your next interview script.

    Exercise: Create Your Individual Experience Maps

    Time: 20 minutes individually, 45–60 minutes with your team

    Do this: Individually first, then share with your trio

    Start by agreeing on the scope of your experience map based on your current outcome. Each member of your trio should then independently create their own experience map using pen and paper (or your favorite digital drawing tool).

    Focus on drawing the customer’s experience, not your product’s features. Where do they get stuck? What goes wrong? How do they work around problems? Don’t worry about drawing well—boxes, arrows, and stick figures are perfectly fine.

    Once everyone has created their individual maps, schedule time to share them with each other. As you explore each person’s perspective, ask questions to understand their thinking. Pay particular attention to the differences between maps—this is where the richest insights emerge.

    Exercise: Co-Create Your Shared Experience Map

    Time: 30 minutes with your team

    Do this: With your product trio

    Bring your individual experience maps together and work to synthesize them into a single shared map. Start by identifying all the unique nodes (distinct moments, actions, or events) across all three maps. Arrange them in a comprehensive flow.

    Collapse similar nodes, but be careful not to overgeneralize. Add links to show relationships and flow between nodes—including loops, error cases, and abandonment points. Finally, add context about what customers are thinking, feeling, and doing at each step.

    As you work, avoid getting bogged down in endless debate. If you disagree about details, draw out the difference rather than debating it. This often reveals you already agree or helps you pinpoint exactly where your understanding differs.

    Remember: This map is your current hypothesis about your customer’s experience. Use it to guide your upcoming customer interviews and plan to evolve it based on what you learn.

    Go Deeper: Additional Reading

    If you prefer an audio summary of this month’s reading, including the book chapters and the following resources, I’ve included an audio version for paid subscribers at the bottom of this post.

    Supplementary Reading

    Why Drawing Maps Sharpens Your Thinking

    Core Concept: Collaborative Decision-Making in a Product Trio

    Other Voices

    To Draw or Not to Draw: Is Traditional Sketching Still Relevant in the Digital Design Era? by Julia Ku

    Journey-Mapping Approaches: 2 Critical Decisions to Make Before You Begin by Kate Kaplan

    The Visual Language of Comic Books Can Improve Brain Health by Mary Widdicks

    Mapping Your User’s Day with the User Clock Sketch by Ben Crothers

    Our Live Discussion Schedule

    Our live discussion sessions are for paid subscribers. Sessions are not recorded. Invitations will go out to Supporting Members and CDH Members two weeks before the scheduled event. But reserve the time on your calendar now.

    Wednesday, March 18, 2026: 9am–10am PDT and 4pm–5pm PDT

    Tuesday, June 16, 2026: 9am–10am PDT and 4pm–5pm PDT

    Thursday, September 17, 2026: 9am–10am PDT and 4pm–5pm PDT

    Wednesday, December 16, 2026: 9am–10am PST and 4pm–5pm PST

    Audio Summary

    This summary was produced by NotebookLM. The sources supplied were the book chapters as well as all of the additional reading.

    Listen here: March — Draw the User Clock to Build Empathy (audio)

    This article is part of the CDH Book Club celebrating the five-year anniversary of Continuous Discovery Habits. See all book club posts.


    Inspired by this post on Product Talk.


    Book a consult png image
  • From Tickets to Strategy: How AI Is Rewriting Support Careers—and Why Now Is the Moment

    From Tickets to Strategy: How AI Is Rewriting Support Careers—and Why Now Is the Moment

    To truly transform with AI, I’ve learned it’s never just about the technology—it’s about redesigning how we work. The teams that win don’t bolt AI on; they re-architect around it. That means rethinking roles, workflows, and governance to build a system that sustains and improves AI performance over time.

    In The 2026 Customer Service Transformation Report, teams at every stage of maturity describe human agents taking on more proactive work—training AI systems, handling the hardest queries, and owning tasks that demand judgment. Job descriptions are shifting, too, with many organizations explicitly adding AI-related responsibilities.

    I’m also seeing a clear rise in dedicated AI specialists. Conversation analysts, knowledge managers, and AI operations leads are fast becoming standard. For support professionals, this opens new, higher-leverage career paths—and creates a talent pipeline that blends service excellence, data fluency, and product thinking.

    Support once centered on queue-level activity—ticket triage, routing, translations, and answering FAQs. Now, as AI handles more frontline interactions, our human roles are moving up the stack toward optimization, oversight, and continuous improvement.

    According to the latest research, 45% of teams report updating job descriptions to include AI-related responsibilities, with 40% saying their human agents are now more focused on training AI systems. Another 27% report that human agents primarily handle the most complex escalations and edge cases, while a quarter say agents are doing more consultative and strategic work.

    Even at the initial deployment stage, 16% of teams report spending less time handling support volume since implementing AI – and among teams who’ve reached maturity, that figure rises to 28%.

    When Intercom’s Research, Analytics & Data Science (RAD) team interviewed 166 of our customers, similar themes emerged. Nearly all participants (≈95%) reported meaningful workflow changes, with manual processes being handled by AI, and humans focusing more on monitoring or fine-tuning AI outputs. Eighty-three percent of participants also reported seeing their team’s roles and responsibilities change to become more strategic and supervisory in nature.

    Infographic of AI-driven customer support roles and adoption rates: conversation analyst 32%, knowledge manager 30%, AI operations lead 28%, support automation specialist 24%; 8% say no new roles added.
    AI is reshaping support teams: organizations are adding conversation analysts (32%), knowledge managers (30%), AI operations leads (28%), and support automation specialists (24%). Just 8% report no new AI roles.

    It’s not just the work that’s evolving; organizational structures are, too. Some teams are reallocating existing talent into AI-focused roles; others are hiring entirely new skill sets. Many of the most common job titles in this space didn’t exist two years ago.

    Consider a Senior AI Knowledge Manager, Beth-Ann Sher, who transitioned from a help center manager role. Like many careers transformed by AI, her work evolved from administrative to strategic. Instead of focusing solely on customer-facing, self-serve content, her mandate expanded to designing and optimizing knowledge inputs that directly improve AI Agent Fin’s performance—work that materially lifts resolution rates.

    Or look at a Senior Conversation Designer, Fred Walton, hired specifically for an AI-first function. He focuses on frictionless customer journeys with Fin, smoothing handoffs between automation and human support while keeping customer satisfaction front and center—hallmarks of mature AI workflows and conversation design.

    In high-performing organizations, roles like these typically sit within a dedicated AI support team under senior CS leadership. Clear ownership and accountability for AI performance is critical; without it, optimization stalls and trust erodes.

    These shifts aren’t isolated. Take Robb Clarke from RB2B. He went from Head of Technical Operations to Head of AI. With Fin, his focus moved from repetitive support questions to managing knowledge and improving the system behind it—freeing him to be proactive about product improvements and fix issues before they hit customers.

    Or consider Eric Broulette from Bloomerang, a support leader who leaned into AI and became the VP of Support and Education. By deploying Fin, his team found breathing room to invest in what’s next. Agents stepped into new roles, contributed to meaningful projects, and built skills that had previously felt out of reach. As Eric puts it: “Do not wait to embrace AI. It will unlock more career growth for your teams than you can imagine.”

    Neon green hero graphic reading 'The 2026 Customer Service Transformation Report', with subhead 'The AI deployment gap is widening' and a black 'Get the report' button over a bar-chart pattern.
    Leaders are racing ahead with real AI in support. Explore the 2026 Customer Service Transformation Report to see where deployment is stalling, benchmark your team, and get practical steps to scale automation that delights.

    Bringing AI into support will eventually change every agent’s day-to-day work. For leaders at the start of the journey, that can feel daunting. My perspective: the most successful teams treat this as an operating model shift, not a tooling rollout—anchored in AI Strategy, governance, and continuous improvement.

    Be transparent about what’s changing, why it matters, and how success will be measured. Define how AI performance will be evaluated (resolution rate, containment, CSAT impact), empower agents to train and improve the system, and communicate how responsibilities will evolve. When teams help build the AI, they’re invested in making it great.

    Here’s the playbook I rely on with support leaders: First, reset expectations about time allocation—less time in the queue, more time improving the AI system that serves the queue. Second, elevate knowledge management as a core capability. Prioritize content quality and coverage for your AI Agent, and carve out dedicated “out of the inbox” time so every agent contributes. Third, keep outcome metrics—especially resolution rate—front and center. It gives the team a north star for experimentation and iteration.

    Scaling AI is as much a people challenge as it is a technology challenge. As automation takes on more work, support roles become more proactive, strategic, and cross-functional—even early in the journey. Responsibilities expand, new roles emerge, and team structures adapt to concentrate on and amplify AI performance. In the process, support careers are transformed.

    If you’re leading this shift, now’s the moment to reimagine your operating model: clarify ownership, invest in knowledge and conversation design, adopt eval-driven development, and build the muscle for continuous improvement. That’s how you move from tickets to strategy—and unlock compounding value for your customers, your business, and your teams.


    Inspired by this post on The Intercom Blog.


    Book a consult png image
  • Scaling Enterprise Sales from $0 to $3.5B: CRO Lessons, MEDDIC Mastery, and GTM Truths

    Scaling Enterprise Sales from $0 to $3.5B: CRO Lessons, MEDDIC Mastery, and GTM Truths

    I’ve led product organizations through multiple growth chapters, and the pattern is always the same: the tighter the alignment between product, sales, and marketing, the faster you scale. Reflecting on the journey of Chris Degnan — the first sales hire at Snowflake who spent 11 years helping scale the company from zero to $3.5 billion in revenue as its CRO while partnering with four different CEOs — I’m struck by how consistently the fundamentals win. The playbook isn’t mysterious; it’s disciplined execution, ruthless clarity, and a go-to-market strategy that matures with each revenue stage.

    At $10M ARR, the CRO role is hands-on and founder-adjacent. You’re close to the product, running point on key deals, pressure-testing messaging, and building credibility with early customers. By $1B+, the job is organization design: segmentation, international expansion, forecast accuracy, enablement, recruiting, and cross-functional orchestration. The shift is from deal quarterback to system architect — standing up repeatable, auditable processes that produce reliable outcomes across regions, segments, and industries.

    Sales leaders who can’t sell the product themselves don’t last. Whether you sit in product management leadership or run the field, you need to master discovery, speak the customer’s language, and translate use cases into value. That also means getting fluent in solutions engineering — understanding integrations, data paths, security, and the operational realities buyers live with. I’ve found this hands-on competence to be the fastest way to earn trust internally and externally, and to keep product strategy grounded in market truth.

    The MEDDIC methodology is the foundation for every durable sales org — and, frankly, a founder’s best insurance policy. MEDDIC forces alignment on qualification criteria, from Metrics to Economic Buyer to Decision Process and Identifying Pain. When product and sales both operate to this standard, roadmap bets improve, marketing targets sharpen, and win rates climb. It’s not paperwork; it’s pattern recognition at scale.

    High-output CROs obsess over the right numbers. Pipeline coverage by segment and stage; conversion rates through each gate; sales cycle length by use case; average selling price and discount discipline; consumption predictability when you have consumption SaaS pricing; and post-sale expansion velocity. The art is deciding which two or three metrics are the organization’s true north at a given stage — then designing enablement, compensation, and operating cadence around them.

    On operating cadence, the week in the life at scale is predictable for a reason. Forecast reviews that surface risk early. Deal reviews that coach to MEDDIC depth, not activity theater. Enablement blocks to uplevel managers and ICs. Recruiting time — always. Customer roadshows to refine value proposition and product positioning. And standing meetings with product, marketing, and finance to keep the GTM motion, roadmap, and unit economics in sync.

    Compensation is a force multiplier or a silent saboteur. Keep it simple, consistent, and aligned to the current motion. Early on, weight new logo acquisition and land quality; as you mature, balance new business with expansion, multi-product adoption, and healthy consumption. Guardrails matter — cap over-discounting, reward multi-threading, and avoid plans that create end-of-quarter cliff behavior. The best plans reinforce the behaviors you want your culture to scale.

    Technical CEOs often underestimate how much narrative, segmentation, and process discipline great GTM requires. The handoff from founder-led GTM to sales-led growth is where many teams stall. My rule: prove one repeatable motion in one segment before you add complexity. Codify the buyer’s journey, instrument the funnel, and make sure product strategy and enablement move in lockstep.

    Culture sets the ceiling. You have to find the fakers, manage-uppers, and passengers quickly — people who look busy but don’t move pipeline, who talk big but avoid accountability, or who ride the momentum of others. The mantra that has saved me endless time: “When there’s doubt, there’s no doubt”. Move fast, but with humanity; be clear on expectations, coach hard, and when it’s not a fit, make the change before the team does it for you.

    Feedback is the operating system of a high-performing org. Leaders at every level need to be coachable — on message discipline, on forecast rigor, on how they develop people. I’ve benefited from straight talkers who hold a high bar, and I try to pay that forward. The fastest way to raise organizational IQ is to institutionalize feedback loops across sales, product, and marketing — from post-mortems to win-loss analysis to field-sourced roadmap reviews.

    What separates exceptional ICs from the rest? Hunger, intellectual honesty, and a builder’s mindset. They qualify hard, align to customer metrics early, multi-thread to power and value, and partner tightly with solutions engineering. They don’t hide from gaps; they surface them, and they know exactly what they need from product, marketing, and leadership to win.

    Executive teams that scale share a few traits: crisp segmentation decisions, single-threaded ownership for outcomes, and healthy conflict that resolves into commitment. Dysfunction, by contrast, looks like metrics roulette, opaque decision-making, and a tolerance for exceptions that become precedent. Make the rules explicit and the exceptions rare.

    Leaders like Frank Slootman have popularized intensity, speed, and focus — and there’s real power there when paired with clarity and data. The lesson I carry forward: move fast on people decisions, keep the message simple, and measure what matters. Equally important is knowing where that approach can backfire — when speed outruns learning, or when pressure erodes cross-functional trust. The best operators balance urgency with systems thinking.

    Most AI companies will face a go-to-market reckoning. Model quality won’t save a weak motion. The winners will articulate a hard-nosed ROI, solve specific workflow pain, address data governance and security head-on, and show measurable lift — not demo dazzle. In other words, the same fundamentals apply; the stakes and scrutiny are just higher.

    If you’re building or rebuilding your revenue engine, start here: define your ideal customer profile and segmentation with ruthless clarity; adopt MEDDIC and teach it across product and sales; align compensation to today’s motion; instrument the funnel and inspect it weekly; and cultivate a culture where feedback is fuel. Do that, and the path from $0 to $3.5B stops feeling like mythology — and starts looking like math.


    Book a consult png image
  • 12 Game-Changing Updates to Fin Procedures & Simulations for Complex Queries

    12 Game-Changing Updates to Fin Procedures & Simulations for Complex Queries

    Today, I’m excited to share 12 major updates to Fin’s Procedures and Simulations—the foundation that lets Fin handle complex work while keeping teams fully in control of the customer experience.

    In my work building AI workflows with product and support leaders, I’ve seen how the right blend of natural language instructions, deterministic controls, and fully agentic behavior turns Fin into a reliable problem solver. Procedures make this blend possible by enabling Fin to act like a human—yet with the repeatability and governance of software. Simulations then let us test those complex Procedures at scale before they reach customers, so we can deploy with confidence.

    Together, these capabilities make Fin self-manageable, transparent, and ready for genuinely complex work.

    Here’s what’s new at a glance: we’ve made Procedures easier to build and maintain; enhanced deterministic controls for precision and policy compliance; expanded agentic behavior so Fin can adapt in real time; and delivered more powerful Simulations to validate end-to-end workflows before go-live.

    Why did we build this? Many teams see early AI gains in speed, coverage, and cost to serve—but then hit a ceiling. They keep AI confined to simple automation and information retrieval, rather than setting it up to handle the nuanced, multi-step workflows they still trust to humans. We designed Procedures and Simulations to remove that ceiling, so teams can confidently set up, govern, and iterate on complex AI workflows without bottlenecks.

    Dark UI diagram of a continuous AI/ML lifecycle loop on a grid, labeled ANALYZE, TRAIN, TEST, and DEPLOY, with TRAIN highlighted in orange to signal iterative model development and evaluation.
    Follow the AI lifecycle as it cycles from Analyze to Train to Test to Deploy. This streamlined loop spotlights the TRAIN phase, underscoring faster iteration and feedback that power more capable procedures and realistic simulations.

    We also heard that teams needed an easy way to connect data so Fin could reliably check customer status or eligibility and then take action. And they didn’t want to route through engineering every time they needed to create or amend logic for mid-conversation decisions. Procedures combines natural language instructions and intuitive data connector setups. You tell Fin in your own words how you want it to behave, and you’ll be guided through creating conditional steps so Fin will react consistently, with the option to add in any code snippets for circumstances where absolute precision is required. Once you build one Procedure, we believe you’ll want to build several, so Fin will constantly read the conversation it’s in to ensure it’s following the most relevant Procedure, and jump to a more relevant one if the user intent changes.

    I know that taking something like this live the first time can feel like a leap of faith. That’s exactly why we built Simulations—to test Procedures comprehensively, uncover edge cases, and launch with confidence.

    Reaching mature deployment takes a deliberate, ongoing commitment to training workflows, validating them before deployment, measuring performance in production, and refining them over time. At Intercom, we call this the Fin Flywheel: train, test, deploy, analyze. Procedures form the foundation of the train stage, and Simulations make the test stage reliable at scale. Together, they enable Fin to handle complex work, and teams to stay in control of it.

    Procedures: Define exactly how Fin handles complex work. With Procedures, I can set Fin up to resolve complex, time-consuming queries that require multiple steps or business logic. Fin follows standard operating procedures and applies sound judgment—just like a seasoned teammate—so even complicated queries are resolved in controllable, predictable ways.

    Interface screenshot of a customer service Procedures editor titled 'Procedure: Damaged food order,' showing when-to-use guidance, Train Fin on examples, and Test, Save, Set live actions.
    A snapshot of the Procedures builder in action, mapping a clear path for handling damaged food orders while letting teams train Fin on examples, target channels, quickly test updates, and publish with Set live.

    Procedures combine three powerful elements. First, natural language instructions. You write a Procedure in plain language, just like documenting a process for a new teammate. You can paste in your existing SOPs, write from scratch, or let AI draft them for you, then iterate yourself.

    What’s new: Draft Procedures with AI. Share an outline of your process and Fin drafts a complete Procedure using your conversation history, knowledge hub content, and relevant data. If additional context is needed, it prompts you with clarifying questions to make sure the Procedure is thorough and tailored to your use case, significantly reducing setup time. For example: if you’re creating a refund workflow, the system can draft conditional paths for eligibility, approval thresholds, and verification steps based on your historical cases and policies.

    What’s new: Break complex workflows into Sub-procedures. Write a process once and reference it across multiple Procedures by breaking it down into reusable steps, called Sub-procedures. This makes workflows easier to read, faster to build, and simpler to maintain as things change.

    Second, deterministic controls. Natural language is flexible, but some steps need to be exact. You can layer in deterministic controls where precision matters, starting with a fully natural language Procedure and introducing structure gradually where it adds value: conditional steps (branching logic) to handle decision points so Fin’s behavior is consistent and predictable; data connectors so Fin can pull information from your tools or take actions automatically; code snippets for when absolute accuracy is essential; and checkpoints to pause for approval or hand off to a teammate.

    Screenshot of a Transaction dispute procedure showing IF/ELSE logic, a code step for check_dispute_eligibility, and a Data Connector menu with Freeze credit card and Get upcoming invoice.
    Fin demonstrates structured troubleshooting: a transaction dispute flow with eligibility checks, clear IF/ELSE steps, and quick Data Connector actions like freezing a card or pulling invoices, streamlining complex support tasks.

    What’s new: Instruct Fin to read specific content from your knowledge hub. You can set clear rules for Fin to reference a specific policy or article from your knowledge hub in defined situations so Fin always surfaces the right context in a conversation.

    What’s new: Explicit Procedure switching under defined conditions. You can set rules that deterministically trigger a switch to a different Procedure, for example, escalating to a complaints Procedure if specific risk signals are detected mid-conversation.

    What’s new: Internal notes for human handoffs. When Fin hands off to a teammate, it can now include internal notes with relevant context so the person picking up the conversation knows exactly what happened and what needs to happen next.

    Third, fully agentic behavior. Because real conversations rarely follow the happy path, Procedures let Fin reason through what’s happening and adapt—jumping to the right step or switching Procedures entirely if a customer changes their mind or the issue shifts.

    Product UI showing a Simulations panel where a 'Food order damage clear' test is running, with a simulated user and Fin AI Agent exchanging messages and green checks marking triggered steps.
    Procedures and Simulations in action: Fin rehearses a food order damage scenario, confirming details and progressing through each trigger. Teams validate complex flows end to end as steps turn green and outcomes are tracked.

    What’s new: Automatic Procedure switching. If a customer starts in a billing workflow but then asks about cancelling their subscription, Fin transitions to the relevant Procedure without forcing the customer to restart.

    What’s new: Structured data extraction from uploaded files. Fin can now extract structured data directly from PDFs and images uploaded by customers—like invoices, forms, or receipts—and use that data within the conversation. Customers don’t have to copy and paste or repeat themselves.

    As MONY Group put it:

    “ If a customer starts down one path but their issue turns out to be something else entirely, Fin adapts seamlessly – no more getting stuck in loops or forcing customers into the wrong workflow. ”

    Screenshot of a Simulations panel for AI support workflows, listing scenarios: Damage confirmed (Pass), Refund subscription (Fail), No subscriptions (Not run yet), with Run all, New, and suggested tests.
    Simulations help teams rehearse procedures and verify outcomes before going live. Run all tests or launch a new one to ensure Fin handles tricky customer scenarios—from damage confirmation to refunds and missing subscriptions.

    The result is a conversation that feels fluid, but always follows your intended rules.

    Making complexity easier to manage is just as important as unlocking new capabilities. Beyond the core updates, we’ve focused on creation, governance, and scale—while keeping ownership with your team.

    What’s new: Improved instruction authoring. We’ve made it easier to write, edit, and structure Procedures, so building and updating them takes less time and requires less effort.

    What’s new: Reporting on when Procedures trigger, resolve, or hand off. You can now track how Procedures are performing directly within the Procedures UI, seeing exactly when they trigger, when they resolve, and when they hand off to a teammate. This visibility helps you spot issues early and improve over time.

    Two-column graphic with customer testimonials on Fin’s Procedures and Simulations update, citing payment query handling, ~94% CSAT for Payment Information, and real-time claims via API-driven decisions.
    Customer stories from Raylo and Mony Group show how Fin now resolves payment issues and complex claims in-chat, checks account data via APIs, and lifts CSAT to about 94%, highlighting the impact of Procedures and Simulations.

    Simulations: Test complex workflows at scale before they reach customers. Simulations let you validate how Procedures will perform before anything goes live, and continuously revalidate as things change. Deploying complex AI can feel uncertain; Simulations remove that uncertainty so you can launch with confidence and iterate safely.

    You can simulate full conversations. For any Procedure, choose a user or customer segment and run a complete, multi-turn simulated conversation. You see every step Fin takes, how it applies your rules, reasons through decisions, and where it passes or fails—giving you the observability to debug and fix issues before they ever reach customers.

    What’s new: Upload images for richer testing. Simulations now support image uploads, so you can test workflows that involve receipts, invoices, or forms—the same inputs your customers actually send.

    What’s new: Clearer visibility into Fin’s reasoning. You can now see exactly how Fin is thinking through each step of a Simulation, making it easier to understand behavior, catch unexpected decisions, and refine Procedures with confidence.

    You can also use AI to create, store, and rerun tests. Writing test coverage manually doesn’t scale. Fin’s AI Assistant generates Simulations directly from your Procedures, suggesting realistic edge cases like partial refund disputes, missing invoice uploads, or no subscription found, so you can expand coverage without expanding overhead. All the Simulations you create are stored in a central library. When a product changes, a policy updates, or a Procedure is edited, hit “run all” to instantly check whether anything has regressed. This applies the same rigor to AI automation that engineering teams bring to software testing.

    What’s new: AI-suggested Simulations. You can now use AI to generate a full set of Simulations from any Procedure. The AI Assistant suggests realistic variations based on your workflow, so you can build comprehensive test coverage fast.

    Customers are already seeing this in production. “Fin can now handle payment-related queries that were never possible before… The impact on CSAT and overall CX has been pretty shocking – the Payment Information procedure CSAT is sitting at ~94%, and CX score is significantly higher than our average.” – Raylo

    “Procedures have fundamentally changed what we can achieve with Fin. Previously, complex processes like cashback claim investigations could only be handled through a static form on our website… Now, Fin can handle these sophisticated scenarios in real-time within the conversation itself. It checks account information via API calls, makes complex decisions, and guides customers through the entire claims process dynamically.” – MONY Group

    Procedures and Simulations are available now. I’m eager to see how teams use these updates to scale agentic AI, deliver faster resolutions, and raise the bar for customer experience—without sacrificing control, compliance, or quality.


    Inspired by this post on The Intercom Blog.


    Book a consult png image
  • Stop Blurring the Lines: Clear Product–Engineering Boundaries to Boost Quality and Prevent Burnout

    Stop Blurring the Lines: Clear Product–Engineering Boundaries to Boost Quality and Prevent Burnout

    Where is the true boundary between product and engineering—and what happens when it gets blurry? I’ve led and coached teams through this question many times, and I’ve learned that clarity here isn’t just a nice-to-have; it’s foundational to quality, velocity, and team health.

    I’ve seen well-intentioned product managers step in to “help” by taking ownership of bug triage, tech debt prioritization, or even system architecture. At first, it feels productive. Over time, it creates role confusion, slows decision-making, and burns out PMs—while paradoxically lowering engineering quality. The “CEO of the product” myth and legacy IT, project-based mindsets are usually at the root. Treating engineers as “order takers” breaks down in evergreen product environments.

    The healthiest collaboration model is simple and disciplined: The product trio owns the “what”; engineering owns the “how”. Product managers are not people managers for engineers—and shouldn’t be accountable for engineering quality. Our job is to frame the problem, align on outcomes, and continuously discover value with customers—not to supervise technical execution.

    If quality is a problem, the solution is escalating and fixing the system, not managing individual bugs. In practice, that means surfacing patterns and elevating them to engineering leadership, who can address root causes—staffing, skills, code health, CI/CD gaps, observability, or process design—rather than asking PMs to paper over issues with status updates. This keeps accountability where it belongs and reinforces outcomes vs output OKRs.

    One high-leverage move is to remove unnecessary intermediaries. Removing the PM as a middleman creates better flow and clearer ownership. Create direct paths for stakeholders to get bug status without routing everything through product. Use dashboards, shared tools, or Slack channels instead of one-off updates. In my teams, shared Jira views, Slack incident channels, and status pages eliminated handoffs, improved stakeholder management, and gave engineers the space to solve problems end-to-end.

    Strong engineering leadership is non-negotiable. What strong engineering leadership should own (and why that matters) is the technical system, quality guardrails, sustainable pace, and the practices that uphold them—incident management, code review rigor, test coverage, and SLOs with SRE. Skilled engineering teams naturally push back when boundaries are crossed—and that’s a good thing. It signals ownership, craft pride, and a pathway to durable execution.

    When do I step in as product? Primarily to clarify desired outcomes, sequencing, and trade-offs—bringing customer and business context to the table. I structure product roadmapping and sprint planning around value slices and risks, not task lists. I align on decision rights early: architecture and tech debt strategies live with engineering; product strategy, positioning, and success metrics live with product; discovery and prioritization live with the product trio.

    Here are the system-level moves I’ve found most effective: Escalate systemic quality issues to engineering leadership, not individual contributors. Advocate for real engineering leadership if your org expects product teams—not IT teams. Then reinforce a culture of continuous discovery so product, design, and engineering make better upstream decisions together. This is how empowered product teams ship higher-quality outcomes—without burning anyone out.

    If you’ve ever found yourself acting as the middleman for bug status or being asked to “own” engineering decisions outside your expertise, you’re not alone. Reset the boundaries, make work visible, and double down on shared outcomes. In my experience, the moment we clarify roles and remove status theater, quality rises, cycle time improves, and everyone does the job they were hired to do—better.


    Inspired by this post on Product Talk.


    Book a consult png image
  • How Deep AI Transforms Support Into Proactive, Omnichannel CX—No Extra Headcount Needed

    How Deep AI Transforms Support Into Proactive, Omnichannel CX—No Extra Headcount Needed

    For years, I chased the elusive goal of delivering a perfect customer experience. Today, with AI embedded in our support operations, that standard is finally within reach—and it’s reshaping how we prioritize, design, and scale service.

    In “The 2026 Customer Service Transformation Report,” teams report early, tangible wins from AI: faster responses, higher efficiency, and consistent coverage across languages and time zones. Those gains create the capacity we’ve always needed. The more we push the technology, the more quality improvements we unlock.

    This marks a fundamental shift. As AI takes on more, our focus can finally move from firefighting to crafting the customer experience. When the AI is working, the measure of success becomes how well it’s working—across accuracy, tone, resolution, and end-to-end journey quality.

    I’ve seen this transformation firsthand. Mature AI deployment gives my team “breathing room,” so we can design for consistently excellent outcomes rather than obsess over deflection. That means widening access to support, removing friction on the path to resolution, and anticipating customer needs before they escalate.

    In our own support organization, we opened support to trial customers, accelerated first response times, and added consultative sessions during onboarding. We absorbed a 300% increase in total demand without adding headcount—made possible by deep integration of an AI Agent and a disciplined AI strategy.

    Infographic comparing ability to meet rising customer expectations: 27% of organizations with mature deployments say support always meets expectations, versus 9% at initial deployment, shown as orange and gray bubbles.
    Teams with mature customer service deployments are nearly three times likelier to say they always meet increasing expectations—27% vs 9% at initial rollout—highlighted by bold orange and gray comparison bubbles.

    Across the industry, the pattern is similar. When teams initially deploy AI, only 9% say they can always meet customer expectations. That number triples as teams reach a mature level of deployment. Even as expectations rise, the organizations that deeply integrate AI—complete with clear ownership, robust instrumentation, and continuous improvement loops—are the ones most likely to meet (and exceed) the bar.

    Looking ahead to 2026, I expect omnichannel consistency to become a key differentiator. The data shows planned investment is distributed nearly equally across chat, email, and social messaging (36% each), closely followed by phone/voice (31%). The question is no longer “Which channel should we optimize?” but “How do we deliver a consistent, AI-powered experience everywhere our customers are?”

    Teams that solve for omnichannel consistency will bridge the long-standing gap between what customers expect and what support can deliver. Every touchpoint becomes an opportunity to exceed expectations and build durable trust.

    Consider Clay, a team that scaled support without sacrificing quality. Support is one of their main growth drivers, and as their customer base expanded, ticket volume surged. Early on, they concentrated much of their effort in Slack, cultivating close, transparent community relationships. But relying on a single channel created friction as they grew; customers wanted the flexibility of email and in-app chat, and Clay needed to deliver the same high standard everywhere.

    Infographic showing channels where teams plan to expand AI usage in 2026: chat 36%, social 36%, email 36%, and phone/voice 31%, displayed as four bold orange blocks with labels.
    Where AI investment is headed for customer service in 2026: chat, social, and email lead at 36%, with phone/voice close behind at 31%. A bold visual snapshot of shifting channel priorities in CX.

    By unifying their support experience with an AI Agent, Clay brought consistency across channels. Today, AI is involved in 90% of all queries and handles half of Clay’s total volume, upwards of 7,000 queries a month. First response rates improved significantly, freeing the team to focus on proactive, high-impact work.

    That work includes identifying content gaps for education and content marketing, reaching customers before they need to ask for help, and surfacing feature requests and recurring challenges to product teams. Clay proves that when support is truly great, it becomes a competitive edge.

    So how do you build a superior customer experience with an AI Agent? Here are five principles I use when scaling toward mature deployment.

    1) Treat customer experience like a product. Treating support as a product means designing, building, and managing the support experience with the same rigor as your core product. You define goals (faster onboarding, higher CSAT or CX Score, lower churn). You map flows (AI starts the conversation, human handovers, proactive nudges). You instrument the journey (track handoffs, drop-offs, success states). You run tests and ship improvements (tone tweaks, fallback paths, training updates). You own the outcomes (gather feedback, measure performance, use insights to continuously improve the system).

    Neon green hero graphic reading 'The 2026 Customer Service Transformation Report', with subhead 'The AI deployment gap is widening' and a black 'Get the report' button over a bar-chart pattern.
    Leaders are racing ahead with real AI in support. Explore the 2026 Customer Service Transformation Report to see where deployment is stalling, benchmark your team, and get practical steps to scale automation that delights.

    2) Lead with AI, back with humans. AI isn’t replacing the human touch. It’s redefining when, where, and how it’s most valuable. In a scaled model, AI is the first responder and the end point for most conversations. Humans step in where they add the most value—particularly during high-stakes issues—and those handoffs should feel seamless. Meanwhile, your team focuses on improving AI performance and optimizing the end-to-end journey.

    3) Be proactive. Use AI to anticipate needs, guide customers before problems arise, and nudge them toward successful outcomes. This is where customer support AI strategy shines—moving from reactive triage to journey orchestration that protects momentum and builds trust.

    4) Build for trust. Many customers still carry the legacy of clunky chatbots that delivered vague answers and dead ends. You earn trust by showing that your system works. Don’t hide your AI Agent behind layers of “choose an option.” Get customers to the AI quickly, demonstrate real problem-solving, and ensure that when a human is needed, they join with full context to resolve complex issues efficiently.

    5) Make it feel personal. Your AI Agent represents your brand. The way it speaks, follows policies, and responds matters. Use tone control, fallback logic, and language preferences to align the experience to your standards. Consistency builds trust; personality builds connection and loyalty.

    Perfect really is possible. With deep AI implementation, you can scale comprehensive, fast, and personal support across channels—so customers feel supported not just when they reach out, but throughout their journey. That’s the promise of modern AI workflows in support, and it’s what will separate leaders from laggards in the years ahead.


    Inspired by this post on The Intercom Blog.


    Book a consult png image