Tag: product management leadership

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.

February 19, 2026
Build a Support System That Scales: How Product Leaders Maximize Impact with Delegation and AI

I hear the same refrain from product leadership peers everywhere: we’re overwhelmed. Shrinking headcount, constant AI disruption, economic uncertainty, and relentless context switching make it feel like we’re carrying two jobs—setting strategy while shielding our teams. I recently listened to an episode of All Things Product that zeroes in on what a real support system for product leaders looks like, and it resonated deeply with my day-to-day.

Want to listen to the conversation yourself? Find it on Spotify or Apple Podcasts.

Here’s the core tension I see (and felt early in my own leadership journey): product leaders tend to underinvest in themselves. We hold onto work because it feels faster, safer, or “just easier if I do it.” But that pattern quietly taxes strategy, slows learning, and caps team throughput. The hidden cost of “doing it all yourself” is real.

Early in my tenure leading product, I tried to keep every plate spinning—roadmap reviews, stakeholder prep, user research, executive updates—while protecting my team’s focus. I was busy and useful, but not maximally valuable. The turning point came when I started building a lightweight support stack: a few hours of executive assistant help each week, targeted research support for bet sizing, and a personal cadence with a leadership coach. The result wasn’t just more time; it was better time.

One provocative point that landed hard: product leaders rarely have executive assistants—and that’s a problem. If your calendar is your operating system, an EA is an extension of your leverage. Mine now handles scheduling, meeting hygiene, prep packets, and post-meeting artifacts. That shift moved me from “calendar triage” to “strategic curation.” It also reinforced a core principle: delegation is a leadership skill, not a weakness. When I delegate outcomes (not just tasks), my team learns, ownership grows, and we ship decisions faster.

Support for strategy work shouldn’t stop at the calendar. Research and data enable better bets. Lightweight research ops, access to product analytics, and brief synthesis sprints keep me anchored in evidence without drowning in artifacts. Paired with a strong community of practice, I get a steady stream of comparative patterns—how other leaders delegate, scope advisory boards, or run decision reviews—which short-circuits trial-and-error.

Coaches were framed as shortcuts for clarity, accountability, and skill-building—and I agree. A good coach compresses cycles, sharpens decision quality, and holds the mirror up when you drift into doer mode. Two quotes captured the mindset perfectly: “You are a pro athlete. It makes sense to think about how you scale your impact without adding more to your calendar.” — Petra Wille. “As you get busier, it becomes more important to focus on the value only you can bring.” — Teresa Torres.

There’s also a helpful nudge to let go of perfectionism: “80% done by someone else is 100% awesome.” — Dan Martell (quoted). In practice, that means I accept great drafts from others, then add the 10–20% only I can contribute—context, narrative, and the sharp edges of the decision.

What about AI? The conversation hits a practical middle ground I share: use AI where it compounds leverage—meeting summaries, research synthesis starters, doc outlines, and backlog triage. But keep humans where judgment, alignment, and context truly matter—strategy framing, stakeholder management, and the final decision-making loops. In other words, apply an AI Strategy that respects product leadership’s uniquely human work.

Key themes I took away: why product leaders struggle to scale themselves; the true cost of “doing it all yourself”; why not having executive assistants limits impact; delegation as a core leadership capability; how to identify and protect the work only you can uniquely do; using research and data to inform strategy; coaches as accelerators for clarity and accountability; communities of practice as a force multiplier; adopting a “professional athlete” mindset; when AI helps—and when humans still matter; and the liberating mantra that “80% done by someone else is 100% awesome.”

If you’re wondering where to begin, start small and practical. Audit your time: what work truly requires you? Experiment with small amounts of support (even a few hours a week). Delegate outcomes, not just tasks. Keep the hands-on work you love—but be intentional. Use peers, coaches, and communities to learn how others delegate. Don’t wait until burnout to build your support system.

Resources mentioned if you want to go deeper: Follow Teresa Torres: https://ProductTalk.org. Follow Petra Wille: https://Petra-Wille.com. Petra’s Coaching for Product Leaders: https://www.petra-wille.com/coaching-packages. Dan Martell’s book Buy Back Your Time: https://www.buybackyourtime.com.

I’m curious: what’s one outcome you’ll delegate this week, and what support would make it stick? Share your thoughts in the comments—your playbook might be exactly what another product leader needs right now.

Inspired by this post on Product Talk.

February 17, 2026
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%.

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.

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:

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.

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.

February 13, 2026
Why “Figma Is Not the Source of Truth”: My Playbook for Design Leadership That Scales

I keep a simple mantra front and center: Figma is not the source of truth. The customer is. In practice, that means the only thing that truly counts is what we ship, how it performs, and whether users come back for more. Mockups are hypotheses; production usage is evidence. When my teams adopt this lens, velocity improves, judgment sharpens, and quality rises where it matters most.

So what does design actually do in a software company? At its best, design builds leverage for the whole system—engineering, product, and marketing—by clarifying problems, raising the quality bar, and making complex decisions legible. The standard I hold is ancient and still essential: products must be useful, usable, and desirable — and above all, used. When we calibrate around “used,” debates about pixels give way to outcomes, and cross-functional partners feel the difference.

I often trace the roots of our craft back well beyond the digital era. The lineage from industrial design to software is real; constraints, ergonomics, affordances, and systems thinking didn’t start with screens. If you’ve ever mapped delight, performance, and reliability in a Kano Model, you’ve touched this lineage. The translation to software is simple: design the full journey, not just the interface—prioritize what improves time-to-value, reduces cognitive load, and earns habitual use.

One lesson I’ve learned the hard way: why design leaders who stop designing stop leading. I still sketch flows, write UX copy, and prototype when it unblocks the team or sets a decisive quality bar. The altitude changes constantly—one hour I’m in a strategic roadmap review, the next I’m in a critique or poking at a prototype. Great design leaders jump up and down in altitude to connect vision to details without becoming a bottleneck.

Over time, I’ve come to rely on four pillars every design manager must master: craft (raising taste and execution), product strategy (clarifying choices and trade-offs), people leadership (coaching, feedback, and hiring), and systems (processes, rituals, and design ops that scale). Neglect any one of these and either quality, speed, or team health will eventually falter.

Perfectionism is a double-edged sword. Over-indexing on quality can paralyze decision-making, but lowering the bar indiscriminately is worse. I’ve seen moments where relaxing standards to “go faster” actually cost the business—rework piled up, trust eroded, and customer value stalled. The answer is principled delegation: I define what “must be true” at each milestone, delegate ownership with clear guardrails, and reserve my veto power for moments where product integrity is genuinely at risk.

Measuring success as a design leader starts with outcomes vs output OKRs. I care about activation, retention, time-to-first-value, NPS verbatims tied to key journeys, and the operational metrics that earn the right to build the next thing. Design output is visible; design outcomes are durable. When trade-offs are needed, I optimize for the smallest shippable surface that still proves the core value proposition, then expand with data.

Scaling judgment is the multiplier. I build it through pattern matching—studying enduring product systems from companies like Airbnb, Amazon, Apple, Asana, Notion, Stripe, Nest, and others—to distinguish where polish compels usage versus where it’s ornamental. Strong opinions matter, but so does being easy to convince with new evidence. I encourage designers to articulate the pattern they’re invoking, why it fits the job-to-be-done, and how we’ll know it worked.

Operating cadence matters. My week is anchored around recruiting, crits, and staff meetings that actually make decisions. In critiques, I use the Do/Try/Consider framework to give actionable direction without micromanaging. On one-on-ones, the question isn’t “Should one-on-ones exist?” but “What are they for right now?”—coaching, performance, or clearing execution blockers. If a meeting doesn’t increase clarity or commitment, it gets redesigned or removed.

Execution-wise, I’ve taken inspiration from Rippling’s operating system—especially its emphasis on speed, precise ownership, and hard commitments. The lesson is timeless: go fast on the right things, make clear promises, and instrument your work so you can see reality quickly. When speed is paired with crisp decision rights and observable outcomes, momentum compounds rather than frays trust.

Hiring your first design leader? Look for someone who can set standards, scale judgment, and ship. They should be able to zoom from company narrative to interaction copy in a single afternoon, coach product trios, and build rituals that make taste and trade-offs explicit. Above all, they should have a point of view on where quality moves the business and where speed is the quality.

Here’s how my team’s approach differs from many: Figma is not the source of truth. We design in Figma, but we learn from production. We pair designers with engineering early, prototype in code when it reduces risk, and wire telemetry into every critical path. Product trios use discovery to validate “useful, usable, desirable — and used,” then commit to outcomes with clear, testable definitions of success. The result is faster iteration, fewer surprises, and experiences customers actually adopt.

If you want to deepen your own pattern library, study products and practices from leaders like Airbnb (https://www.airbnb.com/), Amazon (https://www.amazon.com/), Apple (https://www.apple.com/), Asana (https://www.asana.com/), CrossFit (https://www.crossfit.com/), Figma (https://www.figma.com/), Honeywell (https://www.honeywell.com/), Nest (https://store.google.com/category/google_nest), Notion (https://www.notion.so/), Retool (https://retool.com/), Rippling (https://www.rippling.com/), and Stripe (https://www.stripe.com/). Pay attention to how they balance versatility with clarity, defaults with flexibility, and speed with trust.

The throughline is simple and demanding: design for reality, not for the board. Keep your standards where they create business value, scale judgment with explicit patterns, and instrument everything so learning never stops. When teams embrace that, the work gets better, customers feel it, and the roadmap starts to pull you forward.

February 12, 2026
From Chaos to Clarity with Claude Code: My Hands-On Playbook for Product Leaders

I’ve been pushing hard to operationalize AI for real product work, and this episode zeroes in on the moment Claude Code stops feeling like a demo and starts behaving like a dependable teammate. If you’ve ever wondered how to go from clever prompts in the browser to durable, repeatable workflows on your machine, this walkthrough is for you.

Listen on: Spotify | Apple Podcasts.

My first honest reaction to installing and configuring the desktop agent was the all-too-relatable “this tool thinks everything is a code repo” reality. That framing helped me reset expectations fast: instead of treating it like a magical universal assistant, I began designing guardrails, context, and repeatable routines—exactly how I’d onboard a new team member.

The shift from Claude-in-the-browser to Claude Code on my machine was the unlock. Locally, it can finally work with my files, folders, and workflows. That meant I could ground it in real artifacts—project docs, meeting notes, product specs, and historical decisions—so responses weren’t just plausible; they were contextual and verifiable.

On setup, I now treat /init and Claude MD files as my product requirements. I define roles, boundaries, and canonical sources up front, then run in a deliberate “walled garden.” The “treat it like an intern” model works beautifully: scope access intentionally, expand privileges as trust grows, and keep a tight audit trail of what it can touch and why.

Surprisingly, task management became my ideal on-ramp. It’s easy to validate, the feedback loops are tight, and the ROI is immediate. I export calendar windows rather than granting full calendar access, then let the agent map priorities into Trello, reconcile time blocks, and surface trade-offs. Fast wins build confidence—mine and the agent’s.

Model switching matters more than I expected. When speed is king and “good enough” will do, Haiku keeps the loop snappy. When stakes are higher—complex synthesis, nuanced product strategy, or gnarly ambiguity—I step up to Claude Opus 4.5. Being intentional about when to optimize for latency versus depth is a quiet superpower.

Web tasks can still spiral. When that happens, I pause its autonomy, toggle to fewer steps, and ask, “What are you doing?” Paired with Claude’s Web fetch tool, this makes the agent explain its chain-of-thought planning without exposing hidden reasoning, so I can spot brittle assumptions, prune distractions, and re-ground the task.

Content retrieval has become a killer workflow. I point the agent at my archives—blog posts, book drafts, transcripts, notes—and ask, “Where have I talked about this before?” It assembles a map of prior art, connects themes I’d forgotten, and prevents me from reinventing work. Over time, this evolves into a Zettelkasten-style research system that upgrades rigor and accelerates synthesis.

I’ve also turned Claude Code into a publishing engine. From a single transcript, it drafts titles, descriptions, show notes, and chapters, then routes artifacts to Ghost for formatting. Before anything ships, I run fact-checking workflows that validate claims against transcripts and research sources. The output improves, but more importantly, the scaffolding makes quality repeatable.

Reusable workflows compound. I rely on slash commands to trigger common jobs, break down larger efforts with sub-agents, and wire in hooks and plugins where external systems are needed. This is agentic AI at its most practical: fewer hero prompts, more reliable processes.

Audience analytics and content prioritization are helpful with caveats. I let the agent cluster themes and flag gaps, then I pressure-test its suggestions against first-party data and strategic goals. As with any model-driven insight, triangulation beats blind faith.

Two metaphors guide my day-to-day. First, Claude Code is like a dog—sometimes it returns with the stick, sometimes it gets lost in the woods. Second, the “intern” framing keeps me honest: don’t hand it the whole company on day one. With that mindset, my output jumped—more volume without sacrificing quality—because the workflow scaffolding got better.

In this episode, I cover what Claude Code is and why it’s useful even if you’re not an engineer, the real difference between the browser experience and running locally, how to shape behavior with /init and Claude MD files, why task management is the perfect proving ground, when to export calendar windows versus connecting directly, and when model-switching makes sense—Haiku for speed, Opus for depth.

I also dig into debugging web tasks by asking “What are you doing?”, content retrieval workflows across personal archives, building reusable slash-command systems with sub-agents, hooks, and plugins, practical publishing stacks from transcripts, fact-checking against transcripts and research sources, and using analytics to prioritize content—with a healthy respect for uncertainty.

If you’ve been trying to make Claude Code feel less like “throwing a stick into the woods,” this is the candid, tactical tour I wish I’d had on day one. Drop your questions and experiments below—I’m eager to compare notes and refine the playbook together.

Inspired by this post on Product Talk.

February 10, 2026
Build CX Scores You Can Defend: My 5-step playbook for transparent, trustworthy AI metrics

“You don’t have to trust the algorithm; you can see exactly why a conversation earned the score it did.”

We recently shared how we redesigned CX Score to deliver deeper, more actionable insights across every conversation. The most common follow-up from support leaders was simpler and incredibly important: “Can I trust it?” It’s the right question—and it’s the one I use as my own bar for whether a metric is ready for the C‑suite.

CS teams are the subject matter experts on customer experience. They understand the nuance of what customers feel, the context behind every interaction, and the difference between a technically resolved issue and a genuinely satisfied customer. I’ve learned, conversation by conversation, that any metric we ship has to capture that nuance at scale—or it doesn’t deserve to be used.

We built CX Score to give support teams a complete view of how their customers feel across every conversation. It surfaces what’s working, what’s not, and why—so leaders can communicate impact clearly and drive change across support, product, and the wider business.

A CX Score in action: repeated CSV export failures trigger a low score and customer frustration, while the AI agent clarifies next steps and gathers details—turning raw signals into actionable support insights.

Here’s exactly how I approached building a trustworthy metric that support leaders can inspect, explain, and defend.

1) It’s grounded in how support teams define quality. I started with how experienced support professionals actually evaluate conversations—collecting real examples of strong, mixed, and poor interactions across industries, identifying the specific factors that shape overall experience, and writing plain-English rules for each. The result: CX Score applies the same criteria a trained support professional would use, not generic LLM assumptions.

2) It’s aligned with human judgment. We created a dataset of thousands of real customer conversations spanning multiple industries, languages, channels, and agent types. Each was manually reviewed by experienced support professionals—with two reviewers per conversation where possible and disagreement resolution to create stable consensus labels. The result: CX Score is trained and tested to behave like an expert reviewer, not a language model making broad guesses.

A modern CX analytics view shows how conversations flow from chat, email, and mobile into AI assistance, then to resolutions and sentiment outcomes—turning messy support data into a single, defensible CX Score.

3) It’s engineered by AI specialists. CX Score isn’t a prompt attached to an LLM. It’s a production system built by Intercom’s AI Group: 37 ML scientists and 350 engineers whose full-time focus is AI for customer service. The system includes specialized handling for long transcripts, model configuration tailored for support language and subtle sentiment, prompt engineering designed to default to neutral when evidence is weak, and a multi-stage evaluation pipeline that checks for precision, consistency, and reliability. The result: A metric built by a team that understands LLM behavior in production support environments, where accuracy and consistency matter most.

4) It’s validated statistically, not qualitatively. Trust requires measurement, not vibes. We tested CX Score across standard ML metrics: Precision (when the model flags a negative experience, how often do humans agree?), recall (how many human-identified issues does it catch?), and F1 score (the balance between both). We set an explicit bar: F1 above 0.8, representing high agreement with human judgment. We reran these evaluations through every revision, checking for regressions or biases, and I focused especially on negative experiences, because a false negative hides a real problem. The result: CX Score meets a measurable standard before it ships—not a gut check, a statistical requirement.

5) It was battle-tested with real customers. Lab accuracy isn’t enough. Customer environments are messy: Varied ticket types, mixed languages, unpredictable edge cases. Before release, we ran a multi-phase field test—shadow-scoring conversations with both old and new models, validating sensible behavior across agent type and conversation length, then rolling out to a controlled customer group who confirmed the scores felt right, reasons were clear, and insights were actionable. The result: CX Score shipped because real teams told us it made sense in practice, not because it passed internal tests.

From conversation to clarity: this visual maps the drivers behind a CX Score. Explore how policy feedback, answer quality, and effort combine to produce defendable insights support leaders can act on.

The importance of explainability. One of the most critical choices I made was ensuring CX Score isn’t a black box. Every score comes with clear reasons, concrete excerpts, and a short explanation of what influenced the rating. This turns the metric into something you can inspect, audit, and explain to executives. You don’t have to trust the algorithm. You can see exactly why a conversation earned the score it did.

A metric that evolves with your business. Customer expectations shift. Products change. AI improves. A trustworthy metric can’t be static. CX Score evolves with the same commitments that shaped its redesign: Evaluate the real signals that shape customer experience, keep the logic simple and interpretable, and ensure leaders can make clear decisions from it. It’s built to be a durable source of truth across every conversation.

The takeaway. In a world where products look the same and AI can generate any interaction, customer experience is one of the few differentiators that actually matters. Support leaders have built that expertise conversation by conversation. What they’ve lacked is a measurement system that could validate it at scale—one that’s reliable enough to report to the C-suite, explainable enough to defend in strategy meetings, and rigorous enough to drive real decisions. That’s what CX Score is designed to be: A metric that reflects the reality support leaders see every day, backed by the technical rigor to make it credible everywhere else.

Want to see CX Score in your workspace? Ask your admin to enable it for your team, and start using explainable AI insights to improve customer experience and coach with confidence.

Inspired by this post on The Intercom Blog.

February 9, 2026
Go Deep or Get Left Behind: How AI Deployment Depth Transforms Customer Service

AI adoption is everywhere. I see more teams every quarter moving from pilots to production—and increasing their budgets accordingly. But the gap between “using AI” and truly transforming with it is widening fast. Launching an AI Agent is easy; building a mature, AI-powered support operation is where the real work—and the real value—lives.

In the new research, the "2026 Customer Service Transformation Report," the difference comes down to depth of deployment. It’s not enough to dabble. Teams that design their operations around AI are pulling away from those who treat AI like a bolt-on feature.

This article kicks off part one of my five-part deep dive into the research. I’ll unpack the data, share what I’ve learned leading product and AI strategy, and translate it into practical steps you can apply now. If you’d like to go straight to the source, you can download the report here.

First, the macro picture: 2,470 global support professionals across industries were surveyed to understand current AI usage, challenges, and the 2026 opportunities. The headline is clear—AI investment is now table stakes. Eighty-two percent of senior leaders say their teams invested in AI in the past year and 87% say they plan to invest in 2026. Those investments are already paying off: Over three-quarters of CS teams (77%) say AI is meeting or exceeding expectations, delivering faster response and resolution times, always-on coverage, cost savings, increased capacity, and multilingual support that scales globally.

And yet, only 10% of organizations say they have reached a "mature" level of deployment, where AI is fully integrated into operations and working at scale. That’s the tell: most teams are skimming the surface and leaving meaningful performance gains on the table.

Most service teams are still early in AI adoption. Only 10% report mature deployment, while 26% are scaling, 35% are in initial rollout, and 26% remain in exploration, with 3% unsure.

When I map the data to what I’ve seen in the field, the maturity difference shows up immediately in outcomes. Teams at mature deployment don’t just automate repetitive tasks; they build AI into critical workflows, give it real responsibility, and iterate continuously. Beyond automating the bulk of their manual work, they’re using AI to proactively engage customers and perform tasks on their behalf.

The results follow. Of the teams that have reached mature deployment, 43% report higher quality and consistency across support—nearly double the rate of those still in the initial deployment stage. That quality shift is how support evolves from a cost center to a value driver. Great experiences don’t just prevent churn; they create advocacy and become a reason customers choose you. The more you trust your AI Agent with meaningful work, the more it creates the conditions for higher-quality, more consistent support.

One example I point to often: Lightspeed. They operate a complex product across regions and languages, with tens of thousands of monthly requests. When they adopted Fin in early 2023, they needed a solution that could scale with that complexity—and they treated the transition like a first-class change program.

They leveraged foundational training and built custom, in-house modules aligned to their processes. They supported their team post-launch and worked closely with leadership to align on the goals and benefits of AI. In a large, distributed org, that executive alignment created ownership and momentum. Their VP of Information Systems, Yamine Gluchow, put it perfectly: "It’s not magic. If you invest in understanding, adoption, and great content, AI performance takes off."

Mature AI Agent rollouts deliver bigger gains in customer service—outperforming initial deployments in automation, proactive engagement, and task completion (63% vs 52%, 51% vs 41%, 45% vs 28%)—showing how depth drives measurable impact.

Their outcomes reflect that depth: An 88% involvement rate. 72% of Fin conversations resolved without human intervention. 43,000+ customer requests resolved monthly. Service in 12+ languages across 100+ countries. Stable CSAT—with improvement in some markets.

What impressed me most was the complexity Fin now resolves. A merchant in France asked about tax invoices—normally a long phone call to check back-end data and explain rules step by step. Instead, Fin handled the conversation in French, provided an accurate end-to-end explanation, and earned positive CSAT. That’s what mature deployment looks like: a system that absorbs complexity and delivers correct, efficient results at scale.

So how do we build toward that level of maturity? In my experience, this journey requires a mindset shift and operational rigor—not just a bigger AI budget.

Rethink how you approach support. If you were building from scratch today, you’d design around AI from day one. As Grant Lee, CEO of Gamma, puts it: "If you want to unlock the real value of AI, you have to design for it, not retrofit around it." Treat AI as infrastructure, not a feature. That shift impacts your org design, workflows, and what “good” looks like.

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.

Secure executive sponsorship early. You won’t scale without C-suite backing. AI reshapes how support works, how teams are structured, how performance is measured, and how cost and value flow. Align your CFO on ROI, your CCO on journey design, and your CEO on customer experience as a strategic advantage. Early wins are great—but the compounding gains only come when leadership backs AI as infrastructure, not a one-off cost save.

Assign clear ownership for AI performance. One common failure mode: no one owns the AI. Stand up an AI operations lead or support ops specialist to review resolution trends and handoffs, tune content and configuration, coordinate on systemic issues, and drive a prioritized improvement roadmap. Without this role, feedback loops break and performance plateaus.

Treat content as critical infrastructure. Your AI Agent is only as good as the knowledge it can access. Ensure coverage for the topics it must handle, keep information accurate and current, and structure content so it’s easy for AI to consume. Make maintenance part of BAU, not a quarterly fire drill. A clean, governed, retrieval-first pipeline dramatically increases autonomous resolution.

Build a continuous improvement system. AI performance isn’t static. Train your AI Agent by expanding its knowledge, refining behavior, and connecting new data sources to handle more scenarios autonomously. Validate changes against real scenarios before they ship. Roll out updates in a controlled way across channels and segments. Use performance data to find patterns—frequent handoffs, low-resolution topics—and decide what to improve next. I often point to the Fin Flywheel (Train → Test → Deploy → Analyze) as a practical example of turning performance data into action.

The big takeaway from the "2026 Customer Service Transformation Report" is encouraging: investment is widespread, and early returns are real. The bigger opportunity is to turn those early wins into durable transformation. Teams leaning into AI as infrastructure—supported by executive alignment, clear ownership, strong content, and a continuous improvement loop—are already separating from the pack.

Next up in this series, I’ll dig into how leading teams measure success. Beyond simple cost savings, mature deployments tie AI to clear ROI and strategic impact—shifting more work into value-adding, revenue-generating territory. Follow along here, or subscribe on LinkedIn to get the next installment in your feed.

Inspired by this post on The Intercom Blog.

February 5, 2026
Two People, Zero Waste: How Earmark’s Agentic AI Turns Meetings into Finished Work

I care about meetings only insofar as they create momentum and outcomes. What if your meetings could actually produce the artifacts you need—specs, tickets, slides—before the call even ends?

I recently listened to an episode of Just Now Possible where Teresa Torres talks with Mark Barbir (CEO) and Sanden Gocka (Co-Founder), the co-founders of Earmark, about building a productivity suite that turns unstructured conversations into finished work in real time. As a product leader, this premise hits the sweet spot of agentic AI, real-time AI workflows, and ruthless focus on outcomes over output.

Listen to this episode on: Spotify | Apple Podcasts

Unlike generic AI notetakers that produce summaries nobody reads, Earmark runs multiple agents in parallel during your meetings—translating engineering jargon, drafting product specs, even spinning up prototypes in Cursor or V0 while you're still talking. That’s the bar I want from AI in the room: finished work, not notes.

What impressed me most was the clarity of their pivot. They moved from an Apple Vision Pro presentation coaching tool to a web-based meeting assistant. I’ve made similar calls: when the distribution path and daily workflow are obvious, you follow the user’s gravity. This shift unlocked a broader surface area—PMs, engineers, design partners—and made agentic workflows useful where work actually happens.

They also turned a technical constraint into a commercial advantage. Their ephemeral (no-storage) architecture became a feature for enterprise sales. I’ve seen this repeatedly in AI risk management: privacy-by-design and clear data governance reduce friction with security reviewers and accelerate procurement. For many enterprises, “we don’t store your data” is the win condition.

Cost discipline was another standout. They tackled the hard problem of making real-time AI affordable—from $70 per meeting down to under a dollar through prompt caching. That’s not just optimization; it’s product strategy. Choices like model selection, context window management, and retrieval-first pipeline design determine whether a feature can scale to every meeting or remains a demo.

On capability design, the team leaned into templates and simulated stakeholders to ship value fast. Template-based agents: Engineering Translator, Make Me Look Smart, Acronym Explainer. Personas that simulate absent team members (security architect, legal, accessibility). This is exactly how I frame early AI workflows: remove friction for the product trio, anticipate blockers, and let the agent do the tedious, error-prone first pass.

They were refreshingly pragmatic about models. Why GPT 4.1 still beats newer models for prose quality in their use case is a reminder that “best” is contextual. When the job-to-be-done is precise prose and production-grade artifacts, consistent quality trumps leaderboard buzz. Of course, they also invest in guardrails to ensure quality and manage hallucinations—another non-negotiable for enterprise adoption.

Search and analysis across time is where many AI products stumble. They explained the limits of vector search for analysis questions across meetings and how they’re building agentic search with multiple retrieval tools (RAG, BM25, metadata queries, bespoke summaries). I couldn’t agree more: analysis requires reasoning over structure, time, and purpose—not just semantic proximity. Layered retrieval with stateful agents beats a single embedding call.

They also articulated a crisp user thesis: design for product managers as the extreme user to solve for everyone. In my experience, if you satisfy the PM’s bar for clarity, traceability, and actionability, engineers, designers, and go-to-market teams benefit immediately. That’s how you earn daily active use, not once-a-week novelty.

For builders curious about the stack and comparables, they discuss services and tools like Assembly AI for speech-to-text, OpenAI API with prompt caching support, and build integrations with Cursor and V0 by Vercel. They also reference Granola as a comparison point and nod to ProductPlan, where both founders previously worked. If you want to try the product, here’s Earmark—a productivity suite where the work completes itself.

If you're a PM drowning in follow-up work or a builder curious about real-time AI architectures, this conversation offers a detailed look at what it takes to ship an AI product that people can't imagine working without. Personally, I see this as a credible path toward an AI chief of staff—their vision goes beyond automating deliverables to orchestrating judgment, compliance signals, and cross-functional readiness.

The episode covers the founder backstory, what Earmark does, comparisons to competitors, unique features, templates and personas, technical decisions, early versions and challenges, optimizing transcript summarization, managing multiple tools and costs, challenges with context and reasoning models, innovative search and retrieval techniques, creating actionable artifacts from meetings, ensuring quality and managing hallucinations, and the future vision for an AI chief of staff. It’s a full-spectrum look at building with agentic AI, not just talking about it.

Podcast transcripts are only available to paid subscribers.

Inspired by this post on Product Talk.

February 5, 2026
Mastering 30,000-Foot Vision and Ground-Level Execution: Systems That Decide Without You

Executive function, for me, is the art and discipline of building systems that make high-quality decisions without my constant involvement. The real unlock isn’t personal heroics; it’s institutionalizing judgment. When I do my job well, teams move faster, ambiguity shrinks, and the organization compounds learning even when I’m not in the room.

Operating simultaneously at 30,000 feet and ground level is the defining muscle of executive leadership. I deliberately switch altitudes. At 30,000 feet, I obsess over strategy, architecture, and resourcing. On the ground, I validate core assumptions with firsthand data, listen for weak signals, and spot process cracks before they widen. Altitude changes are not random; they’re triggered by variance from plan, critical customer moments, or leading indicators that deviate from expected ranges.

The leap from frontline manager to manager of managers is where many rising leaders stall. As a manager of managers, my primary value shifts from personal execution to system design. I move from answering questions to installing mechanisms that ensure questions get answered well by others. This includes clear decision rights, shared metrics, and repeatable, lightweight rituals that scale across teams.

What is an executive actually accountable for? Outcomes over output, talent density, and the clarity of the operating system. That means defining strategy, aligning resources, creating a cadence of review that exposes truth, and ensuring incentives reward the behaviors we want. My barometer: if I step away, do priorities hold, do metrics behave as expected, and do tradeoffs land where I would have landed?

Knowing when to dive deep versus when to step back is a craft. I dive deep when risks are existential, when metrics have no credible owner, or when narrative and numbers diverge. I step back when leaders demonstrate consistent judgment, metrics sit inside control limits, and learnings are documented. The principle I return to again and again: context is everything. Senior leaders operate on context, not control.

To scale judgment, I teach people how I think. I externalize my mental models: how I construct decision trees, how I stress-test assumptions, and how I weigh time horizons. I rely heavily on driver trees for metrics because they force causal clarity. If we can’t map how a top-line goal decomposes into controllable levers, we’re managing by hope, not design.

Creating a shared language across the business is a force multiplier. I standardize definitions for our core metrics, codify what “good” looks like, and make it easy to repeat the system. We align around outcomes versus output, and we use cadences like MBRs and QBRs to unify narrative and numbers. Shared language makes decisions legible across functions and reduces rework.

My COO playbook emphasizes owning the full customer experience end to end. When marketing rolls up under a COO in certain stages, the upside is coherence: one narrative from awareness to activation to expansion, one set of metrics, one growth engine. The point isn’t org charts; it’s removing seams customers can feel.

Demanding and supportive is not a contradiction. I set ambitious, unambiguous bars and back them with coaching, resourcing, and fast feedback. The combination builds trust: expectations are clear, and help is immediate. I expect leaders to bring problems paired with proposed solutions and to escalate early, not perfectly.

Inside my executive interview process, I’m assessing altitude agility, operating cadence, and taste in metrics. I use structured interviews and live case workshops to see how candidates frame ambiguous problems, build driver trees, and prioritize tradeoffs. The best prompts are simple and revealing: design the operating system for a 3x scale scenario; diagnose a broken funnel with incomplete data; align two teams with conflicting incentives. The workshop prompts that reveal everything surface thinking speed, humility, and the instinct to make context legible.

The common thread in failed executive hires is a mismatch between the company’s operating system and the leader’s default mode. Some leaders can’t stop doing the work themselves. Others stay too abstract and never build mechanisms. I look for demonstrated ability to change systems, not just run them—leaders who can both author and evolve the playbook.

On metrics, I practice the driver tree philosophy. I begin with the North Star, decompose it into controllable levers, instrument each node, and assign single-threaded owners. We design review cadences where deviations trigger targeted diagnostics, not thrash. Each tree has documented assumptions, data sources, and thresholds that prompt action. This is how teams learn to anticipate, not react.

High-functioning executive teams are visibly collaborative. We clarify decision rights, disagree and commit quickly, and conduct post-decisions to harvest learnings without blame. My favorite litmus test is simple: can 30 people operate as one team when it matters? When we get this right, information flows, execution accelerates, and customers feel consistency.

One of the most counterintuitive leadership lessons is working yourself out of a job. If the system cannot run without you, you have a key-man risk, not a leadership strength. I aim to build successors, codify judgment, and design mechanisms that make good decisions the default state. That’s how you create durable, compounding advantage.

And the review feedback you can’t unhear? Mine was brutally honest: my bar was high, but my mechanisms were implicit. Once I wrote them down—how I decide, what I expect, where I dive deep—the organization moved faster, and I actually became less central. If there’s a throughline to extraordinary leadership, it’s this: make your judgment teachable and your systems inevitable.

February 5, 2026
From Coaching to Co‑Pilots: How AI Elevates Product Owners and Feature Teams

After two decades of coaching product teams, I’m making a deliberate shift in how I guide leaders and practitioners. The destination hasn’t changed—great products, empowered product teams, and durable outcomes—but the route has. AI is now a practical, compounding advantage, and it demands we evolve our product coaching model.

In my day-to-day as a VP of Product Management at HighLevel, I’ve watched AI move from novelty to necessity. Large language models, agentic AI, and streamlined AI workflows now accelerate how we discover opportunities, test hypotheses, and communicate decisions. This is not about replacing product judgment; it’s about augmenting it with a disciplined AI Strategy.

For years, I’ve raised the alarm about the gap between execution and strategy among “product owners and feature team product managers.” The intent was never to pile on more process. It was to strengthen product discovery, sharpen product strategy, and clarify outcomes vs output OKRs so that teams ship what matters. AI finally gives us the leverage to make that shift unavoidable—and repeatable.

Here’s the new coaching stance: treat AI as a co-pilot, not an answer engine. I coach teams to build an AI product toolbox they can trust—prompt engineering patterns, eval-driven development to measure model quality, and a retrieval-first pipeline for institutional knowledge. When combined with continuous discovery, this creates a tight loop between insight, iteration, and impact.

Practically, this means elevating core rituals. In product trios, we start discovery with AI-assisted opportunity mapping, then pressure-test problem framing with user evidence. We generate multiple solution sketches with LLMs for product managers, annotate assumptions, and use A/B testing with a minimum detectable effect (MDE) to validate the riskiest bets. The result is faster learning without skipping the hard thinking.

On the governance side, I set clear guardrails: privacy-by-design, data governance, AI risk management, and explicit criteria for acceptable model behavior. We treat prompts and evaluation datasets as versioned assets, and we pair product managers with forward deployed engineers to operationalize insights in production safely.

Coaching also extends to measurement. We anchor product outcomes in the customer journey and watch leading indicators for activation, adoption, and retention. On the delivery side, we look at deployment frequency and the health of the feedback loop between support signals and roadmap choices—because empowered product teams win when they learn faster than the market shifts.

The most profound cultural change is mindset. Instead of asking AI for answers, we ask it for alternatives, counterexamples, and structured ways to explain tradeoffs to stakeholders. That makes product positioning clearer, decision narratives stronger, and the path from insight to execution shorter.

If you’re responsible for developing talent, reframe coaching as enablement plus guardrails. Build the AI muscle into everyday discovery and delivery, not as a side project. When we do this well, we transform good practitioners into strategic operators—people who pair judgment with leverage and consistently ship value.

The bottom line: AI doesn’t replace the craft; it amplifies it. Our job as leaders is to harness that amplification responsibly and turn it into a durable competitive advantage.

Inspired by this post on SVPG.

February 4, 2026
How We Built Rock-Solid AI Infrastructure: Lessons From Scaling AI Visibility and Reliability

Scaling AI Visibility pushed me to rethink what “reliable” really means for AI infrastructure. As my team expanded usage across more datasets, models, and workflows, we uncovered unexpected sources of report failure and built the guardrails, observability, and processes that now anchor our stability strategy.

In practice, the surprising failure modes were rarely the loud ones. We saw report failure triggered by small schema drift from non-deterministic LLM outputs, silent permission changes in upstream data sources, token-limit truncation that broke downstream parsing, third-party API rate limits that surfaced only under bursty load, and clock skew that confused idempotent writes. Individually these issues looked minor; together they created reliability debt.

Our first move was deep observability. We instrumented the end-to-end pipeline with structured logs, distributed tracing, and high-signal metrics mapped to SLOs and error budgets. That visibility let us separate symptom from cause, quantify impact by segment, and prioritize fixes that moved business outcomes, not just vanity thresholds. It also gave product managers and SREs a shared, real-time view to make tradeoffs explicit.

Next, we hardened the runtime with resilience patterns: circuit breakers on flaky dependencies, timeouts tuned to p95 behavior, retries with jittered backoff, idempotent processing for at-least-once delivery, and backpressure-aware queues. We enforced schema contracts at ingestion with JSON validation and added feature flags to decouple deploys from releases, so we could roll forward or back within minutes when signals degraded.

On the product side, we adopted eval-driven development for model and prompt changes, shifting risky modifications behind canaries and staged rollouts. CI/CD gates required evaluation baselines to hold or improve before promotion. We tracked DORA metrics to keep deployment frequency high without sacrificing change failure rate, and we used P95 latency and budget burn as the forcing functions for prioritization.

Culture mattered as much as code. We formalized incident management with clear ownership, lightweight runbooks, and blameless reviews that produced crisp, automatable actions. We partnered early with SRE on SLO design, integrated privacy-by-design and PII scanning into the pipeline, and treated AI risk management as an ongoing product constraint rather than a checkbox.

The net effect: fewer flaky reports, faster recovery when things do break, and far more confidence to ship improvements to AI Visibility at pace. If you’re scaling similar capabilities, start with observability, make resilience patterns non-negotiable, and let SLOs guide your product roadmap. Reliability is not a phase—it’s the product.

Inspired by this post on Amplitude – Best Practices.

February 4, 2026
Inside Amplitude’s AI Playbook: Lessons from Leo Jiang on Ask Amplitude, Agents, and Visibility

I continually study how high-velocity teams turn AI ambition into shipped product, and Amplitude’s approach stands out. "Leo Jiang is the Head of Engineering, AI Products at Amplitude, focused on building new AI and marketing products. He has helped build Ask Amplitude, Agents, and AI Visibility." From a product management leadership lens, that portfolio signals a clear AI strategy: enable insight (Ask Amplitude), drive action (Agents), and ensure trust and observability (AI Visibility).

What I appreciate most is the sequencing: start with user-facing value, build agentic AI capabilities where tasks repeat and outcomes can be evaluated, and layer AI workflows with robust governance. For PMs and LLMs for product managers, the implication is to define success via eval-driven development—quantitative rubrics, offline test sets, and real-time feedback loops—before scaling automation. This also hints at an emerging discipline of Agent Analytics: instrument prompts, tool calls, and outcome quality so we can tune performance like we tune a funnel.

Ask Amplitude gives a relatable example: natural-language questions lower the activation barrier for product and growth teams inside an Amplitude analytics environment. When agents turn answers into next-best actions, product-led growth becomes measurable—from hypothesis to change to impact—inside a unified decision loop. That tight loop is where product strategy, design, and reliability meet to create compounding value.

Operationally, I organize a product trio around each capability and pair it with forward deployed engineers to accelerate discovery with customers. I also invest in privacy-by-design and data governance early, ensuring marketing use cases respect compliance while keeping iteration speed high. The goal is a repeatable path from prototype to scale that preserves momentum without compromising safety.

My takeaway for peers: pick one high-frequency workflow, define clear agent boundaries, ship a narrow slice, and measure relentlessly. Use retrieval-first pipeline patterns for grounding, add human-in-the-loop checkpoints, and close the loop with qualitative insights from in-app guides. When that works, expand capabilities—not just features—and let outcomes vs output OKRs steer prioritization.

Inspired by this post on Amplitude – Best Practices.

February 4, 2026