Tag: retention analysis

  • 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.


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  • Real-Time Answers in Slack and Teams: How Amplitude’s Global Agent Elevates Product Decisions

    Real-Time Answers in Slack and Teams: How Amplitude’s Global Agent Elevates Product Decisions

    I’ve been looking for a pragmatic way to put product analytics where my teams already work—inside Slack and Microsoft Teams. The moment insights are one message away, cycle time shrinks, debates get crisper, and experiments move faster. That’s why I’m bringing Amplitude Global Agent into our daily decision flow to deliver instant, source-backed answers with visual clarity and actionable next steps.

    Connect Amplitude Global Agent to Slack or Microsoft Teams to answer questions with source-backed analytics, charts, and recommended actions like A/B tests.

    What excites me most is the shift from dashboards to dialogue. Instead of digging through reports, I can ask a focused question in Slack—“How did activation change week-over-week for our self-serve cohort?”—and get a chart in-channel, complete with recommendations that point me toward the next best move. This is Agent Analytics done right: faster insight loops, reduced context switching, and more confidence in the decisions we make every day.

    From a product management perspective, this integration strengthens continuous discovery and aligns product trios around the same truth. Engineers, designers, and PMs see the same chart, discuss trade-offs in the same thread, and can agree on an action—often an A/B test—within minutes. It’s a lightweight but powerful way to support product-led growth and keep our roadmap tied to measurable outcomes.

    In practice, the questions I ask the most look like this: “Which onboarding step causes the biggest drop-off this month?”, “Which channels drive the highest L28 activation rate?”, and “Where did retention improve after our pricing change?” In each case, the Agent returns charts we can share instantly with stakeholders, plus recommended actions like A/B test ideas to validate hypotheses quickly. The result is a reliable rhythm: ask, see, align, act.

    Governance matters just as much as speed. We’re configuring strict permissions, role-based access, and purposeful channel placement so analytics land where they should—no broader, no narrower. We’re also leaning into clear query prompts and naming conventions for events and properties to help the Agent retrieve precisely what’s needed, every time. The aim is a high-signal, low-noise system that maintains trust while accelerating decisions.

    To embed this into our operating cadence, I plug the Agent into three moments: daily standups (to scan activation, conversion, and incidents), weekly product reviews (to align on experiment status and next bets), and executive QBR prep (to pull clean, shareable charts fast). Because the insights arrive in Slack or Microsoft Teams, our conversations stay focused and traceable, and decisions get documented in the same place they were discussed.

    We’ll measure impact with simple, telltale indicators: fewer ad-hoc analytics requests, faster time from question to decision, increased A/B test velocity, and clearer links between recommended actions and outcome metrics like activation and retention. My bar is straightforward—if this Agent can help one team make a better decision per day, it will more than pay for itself across the org.

    If you’re considering a similar move, start small: connect one high-signal channel, curate a handful of common queries, and coach your team on good prompts. Within a week, you’ll feel the difference. When analytics become conversational, momentum follows—and your product strategy benefits from sharper, faster, and more transparent decision-making.


    Inspired by this post on Amplitude – Best Practices.


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  • 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.


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  • Inside Partner Product Marketing: Lessons that Elevate Go-to-Market and Product-Led Growth

    Inside Partner Product Marketing: Lessons that Elevate Go-to-Market and Product-Led Growth

    I’ve learned that the most effective partner product marketing is less about decks and more about decisions. When I collaborate with partner product marketing managers, we translate complex capabilities from a unified analytics platform into crisp, outcome-led narratives that customers can act on. This is where product positioning and go-to-market strategy intersect to create momentum for product-led growth.

    In my experience, the strongest partner product marketing managers operate like solution orchestrators. They align value propositions across partners, clarify the problem-solution fit, and articulate competitive differentiation without drowning teams in feature lists. By anchoring messaging in clear customer pains and measurable gains, they help everyone—from solutions engineering to sales—tell the same story with confidence.

    My playbook starts with outcomes. We define the “why” in terms customers care about, then quantify it with retention analysis, user activation, and time-to-value. That evidence shapes positioning, enables tighter points of parity and differentiation, and ensures our value proposition resonates in market. The result is faster alignment and fewer cycles spent debating messaging without data.

    Cross-functional execution makes or breaks the strategy. I partner closely with solutions engineering to validate solution patterns, and with sales to balance sales-led motions alongside product-led growth. Strong stakeholder management keeps discovery loops tight: we capture objections early, refine narratives quickly, and reduce friction across the funnel.

    On the tactics side, I rely on A/B testing to de-risk bold messaging changes and to optimize in-app guides and product tours. We set a minimum detectable effect upfront, instrument journeys with Amplitude analytics, and iterate quickly. This gives the team statistical confidence while keeping speed high—especially when refining narratives for complex partner solutions.

    Ultimately, great partner product marketing illuminates the shortest path from capability to customer value. When we pair disciplined positioning with data-driven learning, we strengthen our go-to-market strategy and build durable competitive advantage. That’s how we turn strong solutions into market-leading stories that win—and keep—customers.


    Inspired by this post on Amplitude – Best Practices.


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  • Make Your Analytics AI-Ready: De-Risk, Measure, and Scale AI-First Products Fast

    Make Your Analytics AI-Ready: De-Risk, Measure, and Scale AI-First Products Fast

    I ask one question before I green‑light any new AI feature: is our analytics truly AI‑ready? If the answer is no, we slow down, because nothing derails an AI roadmap faster than shipping features we can’t measure, iterate, or trust. Over time, I’ve learned that the right analytics foundation is the difference between a flashy demo and a durable, compounding product advantage.

    "Product and engineering teams face new challenges when building AI-first products. A modern digital analytics platform offers solutions." I agree—and I’d add that the real win comes when model metrics and product outcomes live in one coherent system, so we can connect every improvement to customer value.

    Here’s what “AI‑ready” analytics means in practice for me: a unified event taxonomy tied to clear user and account identities; consistent product analytics (activation, funnels, retention analysis, cohorts); ground‑truth labels and feedback signals for model evaluation; and a single source of truth that blends model telemetry with user behavior. When those pieces click, our AI Strategy turns from guessing to “eval‑driven development.”

    Start with data governance and privacy‑by‑design. Define event names, properties, and versioning rules up front. Capture the context that AI needs—inputs, outputs, confidence scores, content types—without storing unnecessary PII. This discipline reduces rework, improves observability, and keeps auditors and customers confident in how we handle data.

    Next, operationalize eval‑driven development. I run offline evaluations with representative datasets, then shadow mode in production, and finally controlled rollouts with A/B testing and feature flags. We set a minimum detectable effect so experiments are conclusive, and we include AI risk management metrics—like safety violations, fallback rates, and moderation triggers—alongside core product KPIs such as activation, task success, and time‑to‑value.

    On the product analytics side, I rely on a unified analytics platform (e.g., Amplitude analytics or similar) to track adoption of AI features: who sees the feature, who tries it, who repeats it, and who retains because of it. Cohort analyses help me isolate lift among target segments; CRM integration connects usage to revenue; and pathing highlights where users need guidance. This is the engine of product‑led growth for AI capabilities.

    Quality and observability complete the loop. I monitor latency, error rates, and cost per successful outcome, but I also watch human‑grounded proxies: thumbs up/down, edits after AI suggestions, and deflection and CSAT for support workflows. These signals feed back into prompt engineering, retrieval quality, and model selection—closing the gap between LLM behavior and customer value.

    None of this works without strong cross‑functional rituals. Product trios align on success metrics before we write a line of code; continuous discovery validates user problems; and QBRs versus OKRs are reconciled so we invest in durable capabilities, not just quarterly spikes. When analytics and discovery move in lockstep, we ship fewer speculative features and more compounding improvements.

    Finally, choose build versus buy intentionally. I buy a robust, scalable analytics substrate and only build the custom AI evals I need for proprietary use cases. With feature flags in CI/CD and automated schema checks, instrumentation becomes part of deployment frequency—not an afterthought. The result is a reliable runway to scale AI‑first products without losing speed, safety, or clarity.

    If you want a quick readiness check: do you have a clean event schema, identity resolution, and governed properties; a measurable definition of activation for each AI feature; offline and online evals connected to business KPIs; guardrails and human feedback in the loop; and dashboards that team leaders actually use? If not, start there. The payoff is faster iteration, lower risk, and a clearer line from AI investment to customer outcomes.


    Inspired by this post on Amplitude – Perspectives.


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  • Unlock Data-Driven Growth: My Take on Analytics, Experimentation, and Personalization Mastery

    Unlock Data-Driven Growth: My Take on Analytics, Experimentation, and Personalization Mastery

    I’m sharing a focused set of insights on analytics, experimentation, and personalization designed to help teams ship smarter, reduce risk, and accelerate outcomes. Drawing on years of leading product teams, I translate complex data practices into practical playbooks you can apply immediately to improve user activation, conversion, and retention.

    My approach starts with a strong measurement foundation. I lean on a unified analytics platform—often powered by tools like Amplitude analytics—to centralize product, marketing, and customer success signals. With clear event taxonomies, consistent governance, and trustworthy dashboards, teams gain a single source of truth to prioritize the right problems and sequence roadmap bets with confidence.

    Experimentation turns insight into evidence. I emphasize A/B testing discipline, including minimum detectable effect (MDE), guardrail metrics, and pre-registered hypotheses. This repeatable system lifts decision quality, shortens feedback loops, and aligns cross-functional partners around what actually moves the needle, not what merely sounds promising.

    Personalization compounds the value of experimentation by delivering the right value to the right segment at the right moment. Thoughtful in-app guides and product tours—rooted in behavioral signals—nudge users through friction points and increase the likelihood of early wins. The result is a more intuitive path to first value, stronger user activation, and healthier long-term engagement.

    Retention is the ultimate scoreboard. I rely on retention analysis, cohorting, and leading-indicator metrics to connect feature usage to durable outcomes. When paired with product-led growth motions, teams can identify activation thresholds, build habit loops, and scale what works without overextending sales or support capacity.

    If you’re getting started, begin with a crisp instrumentation plan, shared definitions, and a lightweight review ritual. Use continuous discovery practices, opportunity solution tree mapping, and driver trees to tie data signals to real user problems. From there, iterate: test small, learn fast, and scale what is proven. Over time, this system becomes a flywheel for product strategy—fewer debates, more evidence, better products.

    In this series, I distill the frameworks, templates, and real-world lessons that have consistently improved outcomes for product teams: how to structure experiment backlogs, how to read funnel breakpoints, how to detect false positives quickly, and how to operationalize analytics for day-to-day decisions. Expect practical guidance you can copy, adapt, and run with immediately.


    Inspired by this post on Amplitude – Perspectives.


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  • Eliminating the Last Bottleneck: Agentic AI in Amplitude That Builds What Matters Faster

    Eliminating the Last Bottleneck: Agentic AI in Amplitude That Builds What Matters Faster

    For years, I’ve watched high-performing product teams run into the same wall: the gap between insight and action. Dashboards multiply, yet decisions stall. That final mile—where we interpret trends, prioritize tradeoffs, and ship changes—remains the last bottleneck. It’s not a data problem; it’s a bandwidth and focus problem.

    Amplitude's AI Analytics Platform takes the next step: agents that investigate, monitor, and act so your team can build what actually matters.

    From my seat leading product at HighLevel, I see “agentic AI” as a structural upgrade to the product operating system. Instead of waiting on human cycles to discover anomalies, craft hypotheses, and trigger the next experiment, Agent Analytics can continuously investigate user behavior, monitor mission-critical metrics, and initiate actions—closing the loop from observation to outcome. That shift transforms analytics from a passive reference layer into an active, decision-making teammate.

    Practically, this matters because empowered product teams win on speed and focus, not on the volume of reports. When agents surface the most material opportunities—say, a sudden drop in activation for a high-value cohort or a retention dip tied to a recent release—we compress time-to-insight and, more importantly, time-to-action. The result is fewer context switches, fewer meetings, and more cycles invested in building meaningful value.

    The most compelling use cases are those that compound: continuous discovery that highlights friction in onboarding flows, proactive retention analysis on at-risk segments, automated experiment prioritization aligned to outcomes vs output OKRs, and closed-loop alerts that trigger workflows in your CRM or in-app guides to accelerate product-led growth. With a unified analytics platform feeding these agents, we can move from reactive analytics to anticipatory product strategy.

    Of course, leverage requires guardrails. I anchor adoption in three pillars: clear decision rights for agents (what they can autonomously act on vs. recommend), transparency in reasoning (so PMs can audit how conclusions were reached), and explicit alignment to key outcomes (activation, retention, expansion). Done right, this is not a replacement for product judgment—it’s an amplifier for it.

    If I were rolling this out today, I’d set a success dashboard that tracks: time-to-insight, time-to-action, percentage of initiatives initiated by agents, impact on North Star metrics, and the reduction in manual analysis hours. I’d also implement lightweight prompts and playbooks—LLMs for product managers—that standardize how we ask better questions and interpret agent outputs.

    The promise here is simple but profound: eliminate the last bottleneck by giving your teams a partner that never sleeps, never tires, and never loses the plot. When agents investigate, monitor, and act, we spend less time arguing about the data and more time building the right things, faster.


    Inspired by this post on Amplitude – Best Practices.


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  • 90% of CROs Will Fall Behind by 2028: Hard-Learned Lessons to Stay Ahead of GTM Change

    90% of CROs Will Fall Behind by 2028: Hard-Learned Lessons to Stay Ahead of GTM Change

    I’ve been reflecting on why so many revenue leaders are at risk of falling behind, and the conclusion is stark: fewer than 10% of current CROs will thrive by 2028. That isn’t hyperbole—it’s a wake-up call for how quickly go-to-market strategy, organizational design, and AI-driven execution are evolving. From my seat leading product, I see the pressure building on the CRO role to orchestrate the entire revenue system, not just run a sales team.

    One story that crystallizes this reality comes from the journey of Stevie Case, the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor’s bet, she exemplifies how unconventional paths can drive unconventional insight. Her trajectory underscores a bigger truth I’ve witnessed across companies: the best revenue leaders aren’t just great sellers—they’re builders who understand product, process, and people at scale.

    Why do early revenue hires fail? In my experience, it’s rarely about raw talent. It’s about fit, scope, and time horizon. Early-stage teams often hire coin-operated closers to sprint for this quarter’s number, when what they actually need are long-term builders who can shape ICP clarity, pipeline math, and repeatable motion. The trap is simple: you hire for momentum before you’ve validated the motion. That misalignment shows up at 00:00 Why early revenue hires fail and again at 04:16 Coin-operated sellers vs. long-term builders—two ideas every founder-led GTM team should internalize before the first half-dozen sales hires.

    What separates a VP of Sales from a top 1% CRO is scope and systems thinking. A true CRO owns the full revenue engine—marketing, sales, solutions engineering, customer success, pricing, channels, and post-sale activation—not just the new-business line. It’s a role defined by precision around 07:44 Metrics, confidence, and velocity and the courage to decide when to centralize vs. decentralize capabilities as you grow. Should CROs lead sales? At 12:04 Should CROs lead sales?, the nuance is clear: yes, if the motion is still coalescing; not necessarily, once the machine is humming and specialization unlocks scale. My rule of thumb: start consolidated for speed of learning; split functions only when interlocks are provably robust.

    There’s a humbling lesson in 16:36 Learning to scale at Twilio and 19:58 Stevie’s scaling mistake at Vanta: copying another company’s operating system, even a world-class one, is an easy way to blunt your edge. Context is king. What worked at Twilio won’t automatically work at a trust management business. That’s why the line at 17:44 “There is no CRO playbook” resonates so deeply. There are principles—org design, segmentation, enablement, compensation, customer activation—but your playbook must be bespoke to your product, pricing, cycle time, and buyer power map.

    22:16 Why Vanta stays 100% sales-led is a reminder that not every high-growth motion demands product-led growth. In categories where compliance, security, and risk shape buying behavior, a consultative, sales-led approach builds trust and shortens time to value—especially when solutions engineering, onboarding, and customer success are tightly choreographed. I’ve seen teams chase PLG headlines while ignoring the higher-ROI path right in front of them: nailing the sales-led experience, from first touch to first value.

    Top CROs plan 24–26 months ahead. 23:16 The value of planning 24-26 months ahead isn’t about creating perfect forecasts; it’s about designing optionality. That means hiring with stage gates, building enablement before you feel “ready,” instrumenting activation and retention early, and pressure-testing your pricing and packaging quarterly. In my org reviews, I push for scenario modeling: what breaks at 2x volume, what centralizes again at 600 headcount, and what competencies must be grown vs. bought.

    On judgment and decision quality, 29:54 When trusting intuition was the wrong call is a familiar leadership tax. Pattern recognition is powerful—until it isn’t. I’ve learned to pair intuition with a data backstop and a lightweight pre-mortem: what would have to be true for this to fail? It’s the same posture I take with AI in GTM. At 30:49 Do humans still have a place in the future of GTM? and AI vs. humans in go-to-market, the answer is yes—but augmented. Humans set narrative, negotiate ambiguity, and build trust; AI accelerates research, writing, discovery, and coaching. The winning motion fuses both.

    I’m often asked which tools materially shift outcomes. For revenue intelligence and operational rigor, I look to systems that compound learning: Gong: https://www.gong.io/, Salesforce: https://www.salesforce.com/, and Cursor: https://cursor.sh/. To study benchmark operating models and developer-led growth infrastructure, Twilio: https://www.twilio.com/ remains instructive. And to understand why trust, security, and compliance can define the entire GTM architecture, Vanta: https://www.vanta.com/ is a useful case study.

    Leadership non-negotiables matter more as you scale. 33:33 Stevie’s leadership non-negotiables reminded me to be explicit about standards: clarity over activity, customer outcomes over internal wins, and auditability over anecdotes. 36:36 The myth of hiring for industry expertise shows up again and again—I’d rather hire for learning velocity, systems thinking, and builder DNA than narrow domain familiarity. And at 40:00 What stays centralized in a 600-person company, remember: centralize what must be consistent (data, tooling, pricing guardrails, core enablement), decentralize what benefits from speed and context (segment plays, partner motions, field marketing).

    If you prefer a structured digest, here’s the operating checklist I use with revenue and product peers: define your ICP and value proposition crisply; hire builders over coin-operated sellers; instrument the first 30 days post-sale (47:09 The hidden leverage of a customer’s first 30 days); align pricing, packaging, and onboarding to activation; model capacity and hiring plans on 24–26 month horizons; decide early what stays centralized; use AI to amplify discovery, coaching, and content while keeping humans front-and-center for trust-building; and cultivate an unvarnished CEO–CRO pact (01:02:30 Unpacking the CEO-CRO dynamic) that aligns on strategy, segmentation, and sequencing.

    For those who want a few timeline highlights: 00:00 Why early revenue hires fail; 02:23 Who to hire at $5M in revenue; 05:57 What excellence looks like in the CRO role; 17:44 “There is no CRO playbook”; 22:16 Why Vanta stays 100% sales-led; 23:16 The value of planning 24-26 months ahead; 47:09 The hidden leverage of a customer’s first 30 days; 53:42 Why the CRO role will face enormous changes by 2028; 58:42 What leaders must do now to stay relevant.

    The throughline is simple and urgent. 53:42 Why the CRO role will face enormous changes by 2028 isn’t a forecast—it’s a present-tense mandate. 58:42 What leaders must do now to stay relevant: build a revenue system, not a sales team; plan further out while executing faster; let AI handle the mechanical so your people can master the human. Those who internalize this shift will be the fewer than 10% of current CROs who thrive by 2028. The rest will be outpaced by change they could have anticipated—and designed for.


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  • What I Learned Scaling Analytics: Candid Lessons on Product Strategy and Product-Market Fit

    What I Learned Scaling Analytics: Candid Lessons on Product Strategy and Product-Market Fit

    I write from a place many product leaders know well—the moment when the data you need to make decisions simply doesn’t exist, and you have to build the capability from the ground up. That firsthand experience with gaps in analytics shaped how I think about product strategy, product discovery, and the relentless pursuit of product-market fit lessons.

    In my work, I lean on continuous discovery to surface the most meaningful problems, then translate those insights into outcomes vs output OKRs that keep teams focused on impact. When we anchor roadmaps to real user behavior and business results, we avoid vanity metrics and create a durable plan that compounds learning over time.

    Execution matters just as much as insight. I rely on rigorous A/B testing, clear minimum detectable effect (MDE) thresholds, and retention analysis to separate signal from noise. This discipline ensures that every iteration—whether it’s a small UX nudge or a bold bet—moves us closer to measurable value for customers and the business.

    None of this works without empowered product teams. I build around product trios that partner tightly across design, engineering, and product, and I foster a product-led growth mindset so we earn activation, engagement, and expansion through the experience itself. The goal is to create a system where learning is fast, ownership is clear, and the user’s job-to-be-done stays front and center.

    On the tooling side, I favor a unified analytics platform so insights are consistent from discovery to deployment. Whether I’m instrumenting funnels with Amplitude analytics or stitching together qualitative and quantitative inputs, the principle is the same: give teams trustworthy, real-time visibility so they can make better decisions, faster.

    If you’re looking to operationalize these practices, you’ll find practical playbooks, decision frameworks, and real-world examples here—built for leaders who want clarity, speed, and confidence in how they discover, ship, and scale products.


    Inspired by this post on Amplitude – Best Practices.


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  • Deeper AI Integration, Clearer ROI: How Mature Deployments Redefine Support Economics

    Deeper AI Integration, Clearer ROI: How Mature Deployments Redefine Support Economics

    Over the last year, I’ve had the same conversation with a lot of support leaders.

    They’ve deployed AI and are seeing initial efficiency gains, but want to push beyond these early results and achieve meaningful transformation.

    When AI is first introduced, the gains show up quickly. Teams resolve higher volumes of queries, free up capacity, and deliver faster responses. But the real opportunity for impact extends well beyond those initial wins. As AI becomes more deeply integrated into support operations, taking on harder, more complex work, those results compound, new ways to create and measure value open up, and the economics of support change entirely. That shift is where I spend most of my time with leaders—turning early efficiency into durable business value.

    This sits at the heart of “The 2026 Customer Service Transformation Report.” In this reflection, I explore how deeper integration compounds impact and why that makes business value easier to articulate across the organization—especially to finance and product peers who need to see outcomes, not just output.

    The teams going deeper are seeing higher returns. The research shows that 62% of support teams have seen their customer service metrics improve since implementing AI, with early wins showing up most clearly in speed and efficiency. But for teams that have reached mature deployment (where AI is fully integrated into operations) that number jumps to 87%.

    Infographic of customer service teams measuring AI ROI by deployment stage: 70% mature, 60% scaling, 43% initial, 35% exploring, shown as donut charts, illustrating the deployment gap.
    As AI programs advance, measurement confidence surges. This chart shows how ROI tracking rises from 35% in exploring to 70% in mature deployments—evidence of a widening execution gap in customer service.

    The same pattern holds for the ability to measure ROI. Among teams in early exploration, just 35% say they can measure their return on AI investment, but for teams at the mature deployment stage, that rises to 70%. In my experience, this is the moment the conversation shifts from “is AI working?” to “how much leverage are we creating?”

    As AI becomes more embedded in support workflows, what teams choose to measure starts to change. In the early stages of deployment, ROI is typically understood through improved customer response times, lower cost to serve, and freeing up capacity. Teams focus on how much time AI creates and whether it’s relieving pressure on the support organization. These signals help validate that the system is working, but they say little about how that capacity is ultimately used.

    As deployments mature, measurement starts to reflect a different intent. Instead of stopping at time saved, teams look at where that capacity is reinvested—into higher value customer work and revenue-generating activities. ROI becomes less about relief and more about leverage. I encourage teams to set targets for capacity redeployment and tie them directly to activation, retention, and expansion outcomes.

    The report data shows this clearly. Across all maturity stages, the most commonly cited measure of ROI is "time freed up that the support team can use to focus on value-adding activities for customers." But at mature deployment, that signal intensifies, with 73% of teams citing it, compared to 56% at early exploration.

    Comparison bar chart on measuring ROI of AI in customer service, showing mature deployments outperform initial: 73% vs 59% for customer value time, 56% vs 34% for revenue-focused time.
    Mature AI deployments reveal clearer ROI: teams report more time freed for value-adding customer work (73% vs 59%) and more hours redirected to revenue-generating tasks (56% vs 34%) than initial rollouts.

    What’s also interesting is that 56% of mature teams say freed capacity is being directed toward revenue-generating activities, up from 34% at initial deployment. That’s a powerful indicator that AI is shifting from a cost narrative to a growth narrative.

    The result is a shift in economic intent: from measuring what AI saves to demonstrating how the capacity it creates is reinvested to drive growth. As a product leader, I anchor this conversation in outcome-based metrics and clear counterfactuals: what would it have cost to deliver the same experience without AI?

    As AI takes on more work, the question moves from “does it save money?” to “how does it change the economics of support?” Legacy support economics were built for linear growth: more customer tickets meant more headcount, more outsourcing, and more software costs. Success was measured through containment—the number of queries that didn’t reach human agents. These models worked when volume and effort were tightly linked, but AI doesn’t scale linearly, and it needs to be evaluated differently.

    To sustain AI investment and expand its impact, teams need to move beyond cost-cutting narratives and build a clearer case for business value. When done right, AI goes far beyond improving support efficiency. It rewires the financial model, breaking the link between support costs and revenue growth, and turning support into a contributor to customer activation, retention, and lifetime value. This means treating your AI Agent as a new workforce capability that changes how your support function creates and captures value. Here’s what value looks like in an AI-first model:

    Two-panel chart on customer service: before AI, support volume and team size rise together; after AI, volume continues upward while team size levels off or declines, indicating ROI from automation.
    Deeper AI integration decouples growth from headcount. This split chart shows support volume surging while team size plateaus, revealing how automation unlocks scale, reduces costs, and makes ROI easier to prove.

    Human productivity: Your team focuses on more strategic areas, not the queue.

    System improvement: Every resolved query makes the system smarter.

    Revenue influence: Support becomes a lever for activation, retention, and growth.

    Organizational agility: You scale service without scaling headcount.

    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.

    How does this look in practice? Intercom offers a compelling example with Fin. What started as a focused effort to improve their customer support experience has become one of the clearest illustrations of what happens when AI is fully embraced across an organization.

    Since 2022, Fin has helped Intercom absorb more than a 300% increase in customer demand while improving the consistency of delivery—including supporting new routes into support for trial customers and website visitors. Today, Fin is involved in 97% of their customers' conversations. Of those, it resolves 83.5% end-to-end, putting their overall automation rate at 81%.

    That depth of deployment allowed Intercom to scale service without scaling headcount. Without Fin, they would have needed at least 100 additional support teammates to meet rising demand and service standards.

    As Fin took on the majority of day-to-day volume, the human support team shifted toward consultative work—helping customers adopt Fin more deeply, succeed faster, and unlock more value from the platform. Intercom now tracks metrics like “direct revenue generated” and “expansion revenue influenced” to understand the impact of these consultative support activities. This repositioned support from a cost center to an active contributor to long-term growth.

    The throughline from The 2026 Customer Service Transformation Report is that deployment depth makes a significant difference. Teams that are investing in deeply integrating AI are reshaping how support scales and contributes to growth. Value becomes clearer as AI takes on more work, and support leaders can articulate that value to the rest of the business.

    The gap between these teams and those still in the early stages is widening. A select group of pioneers are setting a new bar for what AI-powered customer service can deliver, and understanding what they’re doing differently is the first step toward closing that gap. If you want to dive deeper into the data and frameworks, you can download the report here: https://www.intercom.com/customer-transformation-report?utm_source=blog&utm_medium=internal&utm_campaign=20260128-report-owned-2026cstransformationreport&utm_content=chapterseries_2


    Inspired by this post on The Intercom Blog.


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  • Amplitude’s AI Visibility Upgrade: Content Generation, Chat Segmentation, Sleeker UI—Why It Matters

    Amplitude’s AI Visibility Upgrade: Content Generation, Chat Segmentation, Sleeker UI—Why It Matters

    I look for analytics upgrades that meaningfully compress time-to-insight for product teams. The newest expansion of Amplitude AI Visibility stands out because it improves how we explore user behavior, automate insight creation, and translate data into action across product-led growth motions.

    Explore the most recent updates to Amplitude AI Visibility, including content generation, AI chat-driven segmentation, better UI, and improved reliability.

    Here’s how I’m thinking about the impact. Content generation can turn raw events into ready-to-share narratives—experiment summaries for A/B testing, cohort deep-dives for retention analysis, and executive briefs that tie outcomes to roadmap decisions. For leaders and ICs alike, this trims the manual lift in Amplitude analytics while keeping the human in the loop to verify context and nuance.

    AI chat-driven segmentation is another meaningful unlock. Instead of clicking through complex filters, I can describe the cohort I want in natural language and iterate quickly. That speeds up continuous segmentation work—spotting activation bottlenecks, isolating churn precursors, or defining cohorts for product-led growth experiments—and keeps the team focused on hypotheses and decisions, not interface friction. With LLMs for product managers, the key is pairing this speed with clear guardrails and validation steps.

    The updated UI matters more than aesthetic polish. A clearer, more consistent experience reduces cognitive load, improves adoption across cross-functional partners, and reinforces a unified analytics platform approach. Improved reliability, paired with strong observability, increases trust in the stack—critical when insights drive roadmap priorities and high-visibility launches.

    Operationally, I’d roll this out with a simple playbook: identify 2–3 high-value use cases (e.g., activation funnel analysis, churn cohort exploration, experiment reporting), define success metrics (time-to-insight, stakeholder adoption, decision velocity), and establish basic AI risk management and data governance guardrails (prompt templates, access policies, and review steps). The goal is to turn AI workflows into a durable capability rather than a one-off novelty.

    Bottom line: these enhancements remove friction between questions and answers. If your team relies on Amplitude analytics, the combination of content generation, AI chat-driven segmentation, a cleaner UI, and stronger reliability should accelerate discovery cycles and help you translate insight into action with greater confidence.


    Inspired by this post on Amplitude – Best Practices.


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  • 12 MCP prompts that rally your whole company around product data and drive adoption

    12 MCP prompts that rally your whole company around product data and drive adoption

    I’ve seen first-hand how quickly a company aligns when product data becomes everyone’s common language. To make that happen at scale, I rely on MCP prompts inside Pendo to turn raw behavioral signals into clear, cross-functional actions. When we give people precise questions to ask of the data, engineering, product, marketing, customer success, and sales move in lockstep—and outcomes follow.

    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.

    What follows are the 12 MCP prompts I use to help teams across the business make better, faster decisions from product analytics, in-app guides, and customer feedback. They’re battle-tested, easy to adapt to your stack, and intentionally written to drive product-led growth and clearer accountability.

    Prompt 1: Show me the activation funnel by segment (SMB, MM, ENT) for the last 90 days, highlight the biggest drop-off steps, and quantify which change would yield the largest absolute lift in activated users.

    Prompt 2: Rank features by adoption velocity over the past 30 days, identify underutilized high-value features by persona, and recommend the top three in-app guide placements to increase engagement.

    Prompt 3: Plot 30/60/90-day retention curves for new users by plan type and persona, flag statistically significant gaps, and suggest two experiments to improve week-two retention.

    Prompt 4: Cluster qualitative feedback (NPS verbatims, support tickets, and in-app survey responses) by theme and feature, summarize the top friction points in one paragraph per theme, and propose fixes ordered by impact and effort.

    Prompt 5: Analyze common user paths after onboarding, surface where users stall or loop, and recommend targeted product tours or tooltips to reduce time-to-first-value.

    Prompt 6: Evaluate the impact of a specific in-app guide on activation rate using an A/B test, report lift with confidence intervals, and include the minimum detectable effect (MDE) assumptions used in the analysis.

    Prompt 7: Identify accounts at churn risk based on declining feature usage, login frequency, and support sentiment; produce a prioritized list with the top three customer success plays for each account.

    Prompt 8: Generate a weekly list of product-qualified leads (PQLs) based on usage thresholds, map them to opportunities in our CRM, and recommend the best follow-up message for sales based on feature interest.

    Prompt 9: Analyze usage distribution across pricing tiers, highlight features driving upgrades, and suggest one packaging change and one in-app nudge to improve conversion to the next plan.

    Prompt 10: Measure time-to-value by persona for a key action, compare pre/post tutorial launch, and quantify the impact of our in-app guides on reducing time-to-first-value.

    Prompt 11: For our last three releases, summarize adoption, top feedback themes, and any regressions; recommend one quick win and one strategic bet for the next sprint.

    Prompt 12: Produce a weekly executive summary with the top three product insights, the KPIs they influence, and clear owner-action pairs across Product, CS, and Marketing.

    When teams start their day with these MCP prompts, product data stops being a report and becomes a decision engine. That’s how we drive adoption, run better experiments, reduce churn, and keep everyone focused on outcomes instead of opinions. If you adapt even a few of these prompts to your context, you’ll feel the shift—more clarity, tighter cycles, and a company moving as one.


    Inspired by this post on Pendo – Best Practices.


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