This is the year to build your personal operating system. For me, that line isn’t a slogan; it’s a commitment to eliminate context switching, compress decision cycles, and turn fragmented information into a reliable source of truth. As a product leader, I needed a system that blends judgment, data, and automation—so I built mine around Claude Code.
When I say “personal operating system,” I mean an integrated set of AI workflows, rituals, and tools that capture knowledge, structure decisions, and automate execution. It’s where product discovery meets delivery: a place to synthesize signals, prioritize with clarity, and move from insight to action without friction. The outcome is fewer ad hoc decisions, more deliberate strategy, and a calmer, more focused day.
Claude Code sits at the center because it helps me translate intent into working software and repeatable processes. I use it to scaffold small utilities, write adapters for APIs, and evolve prompts into robust patterns. It accelerates everything from research synthesis and PRD drafting to backlog grooming and stakeholder updates—while keeping me in the loop for final judgment.
Under the hood, I run a retrieval-first pipeline that connects notes, docs, tickets, research transcripts, and roadmaps into a searchable, living memory. With careful context window management, I feed only the most relevant snippets into Claude Code, preserving accuracy and speed. The result: richer answers, fewer hallucinations, and an assistant that “remembers” what matters without drowning in noise.
My daily loop is simple: capture, synthesize, decide, and act. I capture customer signals and meeting notes into a personal knowledge management vault; synthesize patterns with prompt engineering that emphasizes evidence; decide using outcomes vs output OKRs; and act by generating drafts, creating tasks, and updating artifacts. Claude Code helps me wire this end-to-end, so the system works even on my busiest days.
If you’re implementing this from scratch, start small. Pick one high-friction workflow—say, product feedback triage—and build a narrow agentic AI flow to classify, summarize, and route items. Use eval-driven development to test prompts against known edge cases. Add guardrails and privacy-by-design practices from day one, then expand to neighboring workflows once the first loop is reliable.
Governance matters. I treat AI risk management, data governance, and security as first-class citizens: limited data scopes, clear audit trails, human-in-the-loop approvals, and rollback plans. Feature flags control changes; observability tracks drift and quality; and a simple playbook documents how we deploy, monitor, and improve the system.
Measure what this personal operating system earns you. Track decision latency, cycle time from signal to action, meeting-to-output ratios, and the signal-to-noise ratio of inputs. When the system is working, you’ll feel it: fewer meetings, more momentum, and sharper product strategy supported by trustworthy AI workflows.
The goal isn’t to automate judgment—it’s to protect it. By letting Claude Code handle the glue work and information wrangling, I preserve energy for high-leverage thinking: positioning, sequencing, and trade-offs. Build your personal operating system now, and make this the year your product practice runs with clarity and composure.
Is hiring broken—or just badly designed? I’ve been sitting with that question after a recent conversation that crystallized what I see across product organizations: AI-fueled application overload, sprawling interview loops, and fuzzy criteria that invite groupthink at exactly the wrong moments. If you’ve ever watched a promising candidate stall out late in the process, you’re not alone. Listen to this episode on: Spotify | Apple Podcasts.
Here’s the reality I’m observing in the market: Layoffs and hiring freezes have flooded the funnel, while AI tools make it trivial to submit hundreds of applications. Companies are overwhelmed, so they respond by adding more interviews and more stakeholders, hoping more touchpoints equal better signal. In practice, that complexity often dilutes accountability and increases noise—especially for product management leadership roles where clarity, not consensus theater, determines success.
I’ve seen too many offers derailed by “one last step.” A candidate clears every structured interview, then a casual lunch or unframed panel suddenly becomes the deciding factor. The team isn’t briefed on what to evaluate, one lukewarm comment lands, and group dynamics cascade into a no-hire. That’s not rigor—it’s randomness masked as prudence.
Groupthink ≠ good hiring decisions. When everyone has veto power, risk-averse no-decisions become the default. Focus-group-style interviews create bias, not signal, and “culture fit” often becomes a proxy for stereotyping or personal preference. As product leaders, we’d never ship a feature based on vibes; we shouldn’t make high-stakes hiring calls that way either.
There’s a better way—and it mirrors how we run great product discovery. Define who you’re hiring before writing the job description. Set clear success metrics for the role. Assign each interviewer specific criteria to evaluate. Treat hiring like product discovery: intentional, structured, and evidence-based. In my teams, that looks like tight scorecards, interviewer calibration, and a decision owner who synthesizes evidence—not a popularity contest where the loudest voice wins.
Chemistry checks still matter, but only when we define what collaboration actually means for the role. Introversion, debate style, or lunch-table small talk are not performance indicators. I look for behaviors we value in empowered product teams—clarity of thinking, healthy dissent, co-creation under constraints—often via a real working session with the future product trio. Diverse teams outperform homogenous ones, even if not everyone “vibes,” so I optimize for complementary strengths over sameness.
If you’re a candidate, remember: When a process feels broken, it’s often not about you. Ask how you’re being evaluated to gauge process maturity; a thoughtful team will happily walk you through their rubric and what great looks like. For structure and support, I’ve seen “Who: The A Method for Hiring” help leaders clarify requirements; “Never Search Alone” and joining a Job Search Council (JSC) can give you peer accountability and sharper narratives. For current openings, I regularly point PMs to Scott Baldwin’s PM job postings on LinkedIn.
My challenge to fellow product leaders: Audit your hiring process the way you’d audit your roadmap. Where are decisions getting stuck? Where are you over-indexing on consensus and under-indexing on evidence? Tighten the criteria, streamline stakeholders, and instrument the funnel so you can learn and improve. The payoff is faster, fairer, more confident decisions—and teams that reflect the rigor we expect in product strategy and stakeholder management.
What’s one change you can make this week—reworking the scorecard, calibrating interviewers, or replacing an unstructured lunch with a real collaboration exercise? Small improvements compound. Let’s build hiring systems that are worthy of the talent we’re trying to attract.
“Continuous Discovery Habits” turns five this year, and I’m celebrating by reading the book together with you. Each month, I’m releasing an in-depth reading guide designed for empowered product teams and product trios—complete with the chapters we’ll read, a preview of the key concepts, short shareable videos, individual and team discussion prompts, team exercises you can run immediately, and additional reading to go deeper.
We’ll discuss each month’s reading in the comments, and we’ll gather quarterly for live calls. If you’re joining late, no problem—I’ll be monitoring comments throughout the year. Start with the current month or go back to January (https://www.producttalk.org/lets-read-continuous-discovery-habits-together-january-2026/). Jump in where it serves you best, ask for help, share what’s working, and connect with other readers any time.
If you want to participate, grab a copy of the book (https://amzn.to/3hGkNYT?ref=producttalk.org)—or dust off your old one—share the “Spread the Love” videos with your colleagues, set aside time to run the team exercises, and register for the community sessions. Let’s do this.
This Month’s Reading
Chapters: Chapter 3: Focusing on Outcomes Over Outputs
Estimated reading time: ~22 minutes
This chapter zeroes in on the critical difference between business outcomes and product outcomes—and why it matters which one your team is assigned; how to translate lagging business metrics into actionable product outcomes you can actually influence; why setting outcomes should be a two-way negotiation between leaders and product trios; when to start with a learning goal versus a performance goal; and five common anti-patterns that derail outcome-focused teams. Need a copy? Grab the book (https://amzn.to/3hGkNYT?ref=producttalk.org).
Share the Love with Friends and Colleagues
We learn best in community. I like to seed conversations across my org with short, high-signal content—especially when I’m shifting a culture from outputs to outcomes and sharpening OKRs. Use these short videos to bring peers into the conversation and invite them to read along:
“What’s an outcome?” (https://videos.producttalk.org/videos/ea9fdab71d1ee3c263/whats-an-outcome?ref=producttalk.org) — The real value of starting with an outcome. “Business outcomes vs. product outcomes” (https://videos.producttalk.org/videos/069fd5b5101ee2c78f/business-outcomes-vs-product-outcomes?ref=producttalk.org) — Why product teams need product outcomes, not business outcomes. “What’s the difference between OKRs and outcomes?” (https://videos.producttalk.org/videos/069fdab61919e4c38f/whats-the-difference-between-okrs-and-outcomes?ref=producttalk.org) — Any outcome can be represented as an OKR. “Understanding revenue model formulas” (https://videos.producttalk.org/videos/799fd5b5101ee2c4f0/understanding-revenue-model-formulas?ref=producttalk.org) — How to identify the business outcomes your company cares about. “Revisit your outcome every quarter” (https://videos.producttalk.org/videos/449fd5b4111ee0cfcd/revisit-your-outcome-every-quarter?ref=producttalk.org) — Don’t abandon your outcome, but do revisit how you measure it.
Reflect and Discuss What You Read
Reflection is the conversion rate optimizer for learning. When we pause to discuss what we’re reading, we retain more and apply it faster—especially in product discovery and product strategy work. This chapter challenges us to update our definition of success: away from features shipped and toward outcomes achieved. This month, I’m examining my own relationship with outcomes—where I’ve been rigorous, where I’ve drifted, and how I can help my teams strengthen day-to-day behaviors.
Individual Reflection
If your team isn’t working toward an outcome, look at the features or projects on your roadmap and ask: What impact are they supposed to have? If they succeed, what customer behavior or business result would change? If your team does have an outcome, consider whether it’s a business outcome, a product outcome, or a traction metric—and how that choice shapes your daily decisions and discovery cadence. Finally, think about the last time your team’s outcome changed: Was it a deliberate strategic shift, or did it feel like ping-ponging from one priority to the next?
Team Discussion
As a team, classify your current outcome: Is it a business outcome, a product outcome, or a traction metric? If it’s a business outcome, identify the leading customer behaviors that would signal momentum; if it’s a traction metric, broaden it to a product outcome that gives you more room to explore. Then, name which of the five anti-patterns (pursuing too many outcomes, ping-ponging, individual outcomes, outputs as outcomes, or tunnel vision) shows up for you and pick one concrete change. Finally, assess how outcomes are set: Are they handed down, or does your product trio co-create them? What would it take to make this a true two-way negotiation?
Put It Into Practice
Understanding the difference between business outcomes and product outcomes is table stakes. Translating one into the other is where product management leadership shows up. These exercises will help you connect company goals to customer behavior, avoid outcomes vs output OKRs traps, and increase your span of control over meaningful change.
Exercise: Map Your Revenue Model
Time: 30 minutes. Do this: Solo first, then share with your team. Start with this question: How does your company make money? Write out the formula for your revenue model. For example, a subscription business might be: Revenue = Number of Customers × Average Monthly Spend × Retention. Once you have the formula, identify each variable as a potential business outcome. Then, for each business outcome, brainstorm two to three product outcomes (customer behaviors or sentiments) that might be leading indicators. Which of these product outcomes is your team best positioned to influence?
Exercise: Audit Your Current Outcome
Time: 45 minutes. Do this: With your product trio. Take your team’s current outcome and run it through a quick diagnostic: Is it a business outcome, product outcome, or traction metric? If it’s a business outcome, what product outcomes might drive it? If it’s a traction metric, how might you broaden it to a product outcome? Is it a leading indicator or a lagging indicator? Can you measure progress weekly, or do you have to wait months? Is it within your team’s span of control? Based on your answers, draft a revised outcome that offers more actionable feedback while still connecting to business value, and prepare to discuss this with your product leader.
Go Deeper: Additional Reading
If you prefer an audio summary of this month’s reading, including the book chapter and the resources below, I’ve included an audio version at the end of this post for paid subscribers.
Related In-Depth Guide: Shifting from Outputs to Outcomes: Why It Matters and How to Get Started (https://www.producttalk.org/shifting-from-outputs-to-outcomes/).
Supplementary Reading: Empower Product Teams with Product Outcomes, Not Business Outcomes (https://www.producttalk.org/2020/05/product-outcomes/). Defining Product Outcomes: The 8 Most Common Mistakes You Should Avoid (https://www.producttalk.org/2022/12/defining-product-outcomes/). Understanding How Product Outcomes Connect to Revenue and Costs (https://www.producttalk.org/2023/04/connecting-product-outcomes-to-revenue-and-costs/). Product in Practice: Iterating to an Actionable Outcome at tails.com (https://www.producttalk.org/2020/08/actionable-outcomes/). Product in Practice: Iterating on Outcomes with Limited Data (https://www.producttalk.org/2023/12/iterating-on-outcomes-with-limited-data/). Measurable Outcomes – All Things Product with Teresa Torres and Petra Wille (https://www.producttalk.org/measurable-outcomes-all-things-product-podcast-with-teresa-torres-petra-wille/).
Other Voices: The Business Equation by Brett Bivens (https://venturedesktop.substack.com/p/the-business-equation?ref=producttalk.org). KPI Trees: How to Bridge the Gap Between Customer Behavior, Product Metrics, and Company Goals by Petra Wille and Shaun Russell (https://www.petra-wille.com/blog/kpi-trees-how-to-bridge-the-gap-between-customer-behavior-product-metrics-and-company-goals?ref=producttalk.org). Persistent Models vs. Point-In-Time Goals by John Cutler (https://cutlefish.substack.com/p/tbm-2553-persistent-models-vs-point?ref=producttalk.org). Is It Time to Ditch the Old SaaS Metrics? by Kyle Poyar (https://openviewpartners.com/blog/saas-metrics-plg/?ref=producttalk.org). How Engagement Metrics Can Be Misleading by Oleg Yakubenkov (https://gopractice.io/blog/how-engagement-metrics-can-be-misleading/?ref=producttalk.org). Subscription Churn Metrics and Benchmarks for Operators by Elena Verna (https://www.elenaverna.com/p/subscription-churn-benchmarks-and?ref=producttalk.org).
Related Courses: Business Fundamentals: Navigate Your Business Context with Confidence (https://learn.producttalk.org/course/business-fundamentals?utm_source=Product+Talk&utm_medium=cdh-book-club-february-2026).
Our Live Discussion Schedule
Our live discussion sessions are for paid subscribers and will not be recorded. Invitations will go out to Supporting Members and CDH Members (http://members.producttalk.org/?ref=producttalk.org) two weeks before each event—reserve time on your calendar now so you can participate fully and bring real examples from your team.
Wednesday, March 18, 2026: 9am–10am PDT and 4pm–5pm PDT. Tuesday, June 16, 2026: 9am–10am PDT and 4pm–5pm PDT. Thursday, September 17, 2026: 9am–10am PDT and 4pm–5pm PDT. Wednesday, December 16, 2026: 9am–10am PST and 4pm–5pm PST.
Audio Summary
Prefer to listen? I’ve included an audio summary—Stop Measuring Code Start Measuring Behavior—at the end of this post so you can review the main ideas on your commute or between meetings.
I’m excited to dive into outcomes with you this month. As a product leader, I’ve seen teams transform their product discovery, product roadmapping and sprint planning, and OKR quality when they anchor on clear product outcomes tied to business value. Let’s build that muscle together and make this a quarter where we stop measuring output and start driving outcomes.
I’ve watched AI adoption accelerate dramatically over the last year, and the momentum is undeniable. Teams everywhere are experimenting, piloting, and operationalizing AI—but the ways they’re doing it, and the outcomes they’re seeing, vary widely.
Our latest research shows that 82% of senior leaders invested in AI for customer service in 2025, and 87% plan to in 2026. That’s the new baseline. The differentiator now is depth—how far AI is embedded into core workflows, accountability, and measurement.
Teams with mature AI are almost twice as likely to achieve higher, more consistent support quality. Our survey shows 43% of advanced adopters citing this benefit compared with 24% of early deployments.
But while most teams are using AI, our 2026 “Customer Service Transformation Report” shows that this usage is not equal. A gap is opening up between teams that have deployed AI at a surface level and those that have integrated it deeply. I see this firsthand: shallow deployments answer FAQs; deep deployments redesign processes, policies, and teams.
Survey results highlight the AI deployment gap: nearly nine in ten organizations with mature AI see improved customer service metrics (87%), compared with 62% across all respondents, visualized with bold circles.
For this year’s report, we surveyed over 2,400 global customer service professionals across a range of industries to see how they’re using AI today, where it’s paying off, and what they’re betting on as they plan for 2026. The findings mirror my experience leading AI Strategy and AI workflows at scale.
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.
We found that for many teams, AI is still doing narrow work like answering simple questions or handling small parts of workflows. These teams are seeing benefits, but only a fraction of what’s possible. Meanwhile, a smaller group is pulling away. They’ve put AI at the core of their service operation, integrating it into critical workflows, giving it more responsibility, and continuously improving it over time. That’s the hallmark of mature deployment.
Customer service priorities are shifting fast. By 2026, improving CX tops the list at 58%, cost and efficiency climb, and quality moves to third as teams prepare to scale operations and evolve skills.
The difference in results and overall support experience – for both teams and customers – is significant. Here’s how I interpret the data and what I recommend to close the gap.
Survey insights from the 2026 customer service transformation report reveal how AI reshapes support roles: 45% of teams updated job descriptions and 40% ramped up AI training, while human agents focus more on complex escalations.
AI adoption is the norm, depth makes the difference. According to senior leaders, 82% of organizations invested in AI in 2025, with 87% planning to invest in the year ahead. Despite this widespread investment, only 10% of teams report having reached a mature level of deployment, where AI is fully integrated into operations and working at scale. In my playbook, maturity means end-to-end ownership of well-defined workflows, robust guardrails, and clear success criteria.
Early AI wins are fueling expansion beyond support. Survey results show 57% cite proven success, 49% aim for a unified customer experience, 33% need to scale without adding headcount, and 31% see demand from other teams.
Reaching this level of maturity is where AI’s real value lies. We found that 43% of teams with mature deployment report higher quality and consistency across support – nearly double the rate of those still in the exploration or initial deployment stages. That aligns with what I see when we move from point solutions to platform thinking and agentic AI patterns.
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.
ROI becomes clearer with deeper integration. The economic benefits of AI tend to show up first in speed and throughput, and they show up fast. Across all respondents, 62% say their customer service metrics have improved since implementing AI. Most often, teams report their initial gains in efficiency and scale—faster responses, shorter handling times, and the ability to resolve more conversations with the same team—all driving lower cost per interaction.
But the deeper teams go with deployment, the more the results start to show in the metrics. We found that among teams that describe their AI deployment as mature, the cohort of respondents reporting improved metrics as a result of AI rises from 62% to 87%. What’s more, teams with more mature deployments are significantly more likely to say they can measure the return on their AI investment. My advice: instrument everything upfront, baseline rigorously, and use eval-driven development to iterate with confidence.
The bar has moved from ‘does it work?’ to ‘is it actually good?’ More than ever, teams are focused on improving customer experience and satisfaction, with 58% saying it’s the top priority for 2026. That number has more than doubled since last year, when just over a quarter (28%) of respondents cited it as a top priority. As AI assumes repetitive work, your people can shift from reactive triage to proactive journey design. Now is the time to invest in quality frameworks, prompt engineering standards, and LLMs for product managers to close the loop between product, ops, and CX.
Important support work now extends beyond the inbox. AI is reorganizing core customer service operations as it starts to take on a higher volume of work and more complex tasks. Even at the initial deployment stage, 16% of teams report spending less time handling support volume since implementing AI – and among teams who’ve reached maturity, that figure rises to 28%. I’ve seen new roles emerge—AI operations managers, conversation designers, and model evaluators—alongside upskilling for agents into higher-order troubleshooting and relationship building.
Support is creating the blueprint for AI deployment across the business. Support was the proving ground for AI, and our research suggests that businesses are now planning to expand its use to other areas based on the results it’s yielded so far. Fifty-two percent of respondents said that their organizations are actively planning to scale AI to departments like customer success, marketing, and sales in 2026. The two most cited driving forces behind this decision are the success support has seen with AI to date and a desire to create a unified customer experience. Treat your support stack as a reusable platform: shared services, governance, and reusable components accelerate adoption in adjacent functions.
Seize the opportunity to close the gap. Having or not having AI isn’t a question anymore. What you should be asking now is how close you are to mature deployment, where AI is capable of tackling nuanced, high-stakes work. Those who have reached this stage show that going deep is what unlocks real value. That’s the opportunity. Push AI to do more, bring it to more channels, use it to resolve the most complex queries, and close the gap before it becomes too wide to close.
This might seem daunting. But trying new things always is. What we’re experiencing now is a defining moment for customer service, and the teams that are leaning in are actively building the future. As this report shows, what works in customer service now will become the blueprint for how organizations transform the full customer journey with AI. If you want the benchmarks and the playbook to accelerate from pilots to production-grade outcomes, I recommend reviewing the full “2026 Customer Service Transformation Report.”
When I set out to operationalize AI across a product organization, I focus on one promise: repeatable outcomes without chaos. An effective AI operating model turns experiments into an engine—aligning strategy, teams, technology, and governance so we can ship value safely and at scale.
At its core, an AI operating model is the connective tissue between vision and delivery. I anchor it on a few pillars: clear AI Strategy, empowered cross-functional teams, a modern AI platform, rigorous AI risk management and data governance, and a cadence of eval-driven development that ties everything back to outcomes.
Strategy comes first. I translate big ambitions into a portfolio of use cases ranked by customer impact, feasibility, and risk. I use continuous discovery to validate the problem, then frame each bet with outcomes vs output OKRs, a crisp value proposition, and a build vs buy decision. For generative AI, I encourage PMs to treat LLMs for product managers as a craft—rapid prototyping, deliberate prompt engineering, and disciplined evaluation from day one.
Team design matters as much as models. I organize around product trios—PM, design, and engineering—augmented by data, ML, and a “forward deployed” mindset when the domain is complex. I invest in empowered product teams and communities of practice to spread patterns quickly while avoiding centralized bottlenecks.
On the platform side, I start retrieval-first pipeline before fancy modeling. A solid foundation—feature stores, vector search, observability, and safe integration points—beats bolt-on hacks. I rely on CI/CD with feature flags, strong deployment frequency, DORA metrics, and SRE-grade reliability to keep the iteration loop tight and safe.
Governance is non-negotiable. I implement privacy-by-design, clear data governance, audit trails, and policy controls aligned to regulatory compliance. AI risk management includes model red teaming, safety layers, and human-in-the-loop review where needed. The goal is confidence: we know what shipped, why it works, and how it fails.
Execution rides on eval-driven development. For every AI workflow, I define offline and online test sets, target metrics, and a decision policy before launch. I A/B test with proper minimum detectable effect (MDE), layer canaries for protection, and monitor user experience and outcomes in production. This is how we turn “it seems smarter” into statistically confident improvements.
Adoption is a product in itself. I build onboarding, in-app guides, and product tours that help users form habits quickly. I monitor activation, time-to-value, and retention analysis while partnering with customer support ai strategy to close the loop between real-world issues and roadmap priorities.
Culture scales the system. I normalize rapid learning, shared playbooks, and personal knowledge management so insights don’t disappear into meetings or notebooks. I upskill teams on prompt engineering, context window management, and model selection, and I celebrate the humility required to refactor what “worked” yesterday.
Operating cadence keeps it all coherent. I run an AI portfolio review tied to outcomes vs output OKRs, keep a single source of truth for evaluations, and align go-to-market strategy with release readiness. We review risks alongside results so speed never outruns safety.
If you’re starting from scratch, I recommend a 30-60-90 approach: baseline your current state, choose two lighthouse use cases, stand up the retrieval-first pipeline and eval harness, define governance and data policies, then ship small, safe increments behind feature flags. Teach the system to learn before you make it run.
I’ve felt the pain of brilliant prototypes that crumble in production and the thrill of AI features that compound value month after month. The difference is the operating model. Build it with intent, and you’ll scale AI with confidence—teams aligned, tech resilient, and customers seeing real outcomes.
“Speed is not the enemy of safety; it is the prerequisite for it.” I live by this principle. In our organization, the average time from merging code to it being used by customers in production is just 12 minutes, and that short window is fundamental to how we build, ship, and learn.
In January 2026, we are averaging 180 ships per workday – roughly 20 deployments every hour. Conventional wisdom suggests that to increase stability, you must slow down. I believe the opposite. Speed is not the enemy of safety; it is the prerequisite for it. Accumulating code creates risk; shipping small batches minimizes it. Shipping is our company’s heartbeat.
Maintaining this frequency while targeting 99.8+% availability has required over a decade of focused investment in systems, principles, and processes. We protect the integrity of our systems through three layers of defense: an automated pipeline that is simple, reliable, and removes the need for manual intervention, a shipping workflow that promotes ownership and uses guardrails as accelerants, and a recovery model that optimizes for mitigating inevitable failures. Here’s how we’ve built each layer so that velocity is our greatest source of stability.
While our platform consists of various services and frontend applications, I’ll focus here on our Ruby on Rails monolith. It is our core application and the one we deploy most frequently; we also deploy it to three different data‑hosting regions with independent pipelines. Our other services follow similar pipeline principles and safeguards, but the Rails monolith is the clearest example of how we ship at scale.
The automated pipeline is designed to move code from merge to production as fast as possible while enforcing strict safety checks. It is fully automated, and the vast majority of releases require no human intervention—critical for CI/CD at high deployment frequency.
Once an engineer merges code to GitHub, two things happen immediately. First, the build: we compile the Rails application and its dependencies into a deployable asset (a slug) in about four minutes. Second, parallel CI: our test suite runs alongside the build; through extensive optimization, parallelization, and test selection, the vast majority of CI builds finish in under five minutes.
As soon as the slug is built, it’s deployed to a pre‑production environment. CI does not block the progression of the slug to pre‑production. Deploying to pre‑production takes around two minutes. This environment serves no customer traffic, but it is connected to our production datastores, mirrors our production infrastructure variants (e.g., web serving, asynchronous worker), and is configured so that requests exercise the pre‑release code and workers.
Immediately after deployment, we run and await several automated approval gates. We verify that the application boots cleanly on hosts (boot test), confirm the parallel test suite passed (CI check), and execute functional synthetics using Datadog Synthetics on critical flows—such as loading or editing a Fin workflow. If any gate fails, the release is halted and does not go to production.
Once approved, we promote the code to thousands of large virtual machines. A deployment orchestrator triggers these deployments simultaneously, while a decentralized, staggered rollout avoids changing the state of the entire fleet at the same millisecond. Within each machine, a rolling restart mechanism removes a process with old code from the serving path, lets it drain gracefully, and replaces it with a fresh process running the new code. From the moment a deployment starts, first requests are served by new code within roughly two minutes, and the vast majority of the global fleet updates transparently within six minutes. When restarts trigger on every machine, production unblocks so the next deployment can begin.
We treat a stalled pipeline as a high‑priority incident. If the automated system rejects three consecutive release attempts, it pages an on‑call engineer. These are pre‑production blocks, but if the shipping lane stops moving, changes pile up—and our stability relies on building and shipping in small steps. The on‑call’s job is to restore flow so that tiny, safe, frequent updates continue to keep risk low.
Our shipping workflow is built on extreme ownership: tools assist, but the engineer is accountable for quality and the decision to merge. I insist that you are present when you ship. The practical benefit of a 12‑minute deployment cycle is that engineers remain in the zone, focused on the problem they just solved, and ready to validate behavior as it goes live.
A rocket lifts into a luminous sky, a metaphor for shipping code fast without breaking things, where precision, automation, and guardrails power 180 safe deployments a day.
To support this, our deployment system sends Slack notifications the moment code is submitted and as it advances through stages, embeds direct observability links to relevant dashboards and logs in every PR and message, and prompts verification so engineers actively watch the dials and test features in production. It is not acceptable to rely on green builds. You’re expected to watch your change go live and if you’re not prepared to rollback, you’re not prepared to ship. We maintain a no‑blame culture: quick rollbacks and immediate reverts are signs of vigilance and ownership, not failure.
We make extensive use of feature flags to turn deployment into a non‑event. By decoupling deployment (moving code to servers) from release (turning features on), we shrink the blast radius of change. Flags can be enabled for all customers, a specific subset, or disabled for everyone in under 60 seconds through our backend UI. Engineers can group flags into beta features and run phased rollouts; we also ensure flags work consistently across non‑monolith applications. In the past three months, we created over 560 flags—and we actively manage them to avoid permanent complexity.
For complex refactors—especially when behavior should not change—we leverage GitHub Scientist, an open‑source experimentation library. It runs candidate logic (new code) in parallel with existing logic (old code) in production, instruments both paths for result and timing comparisons, and keeps existing behavior user‑visible. That means we can iterate on and validate new code under real load without risking the experience, then switch seamlessly when confident.
When engineers need to go deeper before merging, they can generate a slug and deploy it to a virtual machine, detaching a running production host from the serving path and connecting for manual testing. They can also put a pre‑release slug on a serving machine that handles a small percentage of jobs or web requests. Single‑host validation lets us slice observability to those hosts, compare against the main release, and make low‑level changes safer. Staging is a simulation; production is reality. Testing on a single production host validates assumptions with real‑world data without risking the fleet.
Our recovery model starts from a simple principle: stop monitoring systems; start monitoring outcomes. Traditional monitoring tells you if a server is healthy; we care whether customers are healthy. We rely on heartbeat metrics—vital signs that represent the core value our product provides—such as the rate at which messages and comments are created.
Unlike standard uptime checks, heartbeat metrics are binary in spirit. If message send rates dip below baseline, it does not matter if infrastructure dashboards are green. Down is down, and if customers can’t do their job, uptime percentages are irrelevant. By tracking real‑world success rates as a high‑level signal, we catch subtle degradations that traditional alerting either misses or over‑alerts on.
Because we ship in small, incremental steps and maintain previous releases on our virtual machines, our Time to Recover (TTR) is generally very fast. If a heartbeat metric drops or a critical anomaly is detected right after a ship, the system can trigger an automatic rollback, reverting to the release that was running 20 minutes ago—often restoring service before an engineer responds. For complex issues, engineers can initiate a manual rollback through our deployment UI; doing so also locks the production pipeline to prevent further releases while we investigate and remove problematic code.
Resumption of service is not the end. Every incident prompts an incident review, and we don’t just fix the bug. We ask, “How did the machine allow this to happen?” Then we harden the system so it cannot happen again. This loop—fast shipping, fast recovery, rigorous learning—compounds resilience over time.
This operating model aligns to DORA metrics: high deployment frequency, short lead time for changes, low change failure rate, and rapid time to restore service. It’s a CI/CD and SRE‑informed approach that converts speed into a defensive advantage rather than a liability.
Shipping 180 times a day isn’t a vanity metric; it’s a deliberate choice to protect the customer experience. With a 12‑minute window from code to customer, the feedback loop is tight and engineers retain context—and accountability—for the immediate impact of their work. Maintaining this pace requires more than fast CI; it requires judgment, extreme ownership, disciplined use of feature flags, and a recovery model that monitors outcomes. We rely on human expertise, augmented by these layers of defense, to catch issues before they turn into customer pain. We don’t ship fast despite our need for stability; we ship fast to stay in control of change.
I see the strongest products emerge where customer outcomes, sales insight, and engineering rigor intersect. That’s precisely why I value the craft of solutions engineering—and why I’m excited to share how Chris Landon exemplifies it.
Chris is a seasoned professional with extensive experience in solutions engineering and sales consultancy. He's currently a senior solutions engineer.
From a product management leadership vantage point, this blend bridges discovery and go-to-market strategy, converts ambiguous requirements into crisp product positioning and value proposition, and ensures we’re solving the right problems for the right personas. The result is a tighter feedback loop between field reality and product intent—an essential ingredient for sustainable product-led growth.
In practice, senior solutions engineers partner closely with product trios, informing product roadmapping and sprint planning with field-tested evidence. In my experience, their input sharpens stakeholder management, de-risks complex integrations, and equips sales with narratives that reflect genuine customer outcomes rather than feature lists.
On the analytics side, the most effective partners help define decision-ready metrics across a unified analytics platform, enriching retention analysis with qualitative context from customer conversations and proofs of value. That closed loop turns demos and early deployments into high-signal inputs for learning, prioritization, and go-to-market strategy.
If you’re building a modern product organization, invest in this partnership. Clarify the value proposition together, test product-market hypotheses with real customers, and translate learnings into clear roadmaps. Leaders like Chris make that collaboration seamless—and the result is not just a stronger product, but a more resilient, customer-centered growth engine.
Inspired by this post on Amplitude – Perspectives.
I just tuned into the latest conversation on the upcoming Product at Heart 2026, and it hit on the exact challenges product leaders are navigating right now: curating meaningful content in a world where AI moves faster than our agendas, designing formats that create real connection, and ensuring every minute earns its place. Listening to Petra Wille and Teresa Torres map out the speaker lineup, workshops, and structural shifts, I found myself nodding along—this is the kind of thoughtful curation we need if we want product teams and product leaders to walk away with practical value, not just inspiration.
Listen to this episode on: Spotify | Apple Podcasts
What stood out immediately is the bold move to a single-track conference for 2026. In an era of gen ai hype and endless breakouts, this choice signals clear intent: tighter curation, a shared experience, and less FOMO. The team isn’t carving out a separate AI track—and I love that decision. Their stance is simple and sensible: No AI track—AI will show up everywhere, but not as a siloed topic. The team sees it as part of the everyday toolkit. That mirrors how high-performing, empowered product teams actually work today—AI Strategy and AI workflows are part of the operating system, not a side show.
The keynote lineup is already compelling. Christian Idiodi (SVPG) brings storytelling that turns product principles into habits you can actually use on Monday. Elaine Kasket, cyber-psychologist, exploring digital afterlife and AI replicas, will push us to think more deeply about the human side of our systems. And Teresa Torres will be sharing what she’s learning about AI—exactly the kind of continuous discovery mindset we need as we integrate LLMs into product discovery and delivery.
I’m also thrilled to see roundtables become what they’re calling an “alternative track.” That’s a smart way to deepen learning without fragmenting attention. The best conference ROI I’ve had often comes from targeted small-group conversations—where product trios compare approaches, swap metrics frameworks, or challenge each other’s product strategy assumptions. It’s a design choice that rewards curiosity and builds communities of practice.
We also get a behind-the-scenes look at Teresa’s Maker Studio workshop, where participants will build personal AI workflows. That’s exactly the hands-on, practitioner-first approach teams need right now—less demo theater, more systems that stick. If your roadmap includes integrating LLMs into continuous discovery or augmenting your team’s decision velocity, this kind of guided practice is gold.
The broader workshop slate looks deep and balanced. Expect returning favorites and practical frameworks: Rich Mironov on the realities of product leadership in complex orgs; Büşra’s metrics workshop translating outcomes into action; and an overview of additional workshops from Rich Mironov, Büşra Coşkuner, Marcus Castenfors, and Özlem Yüce. From success metrics to toolkits for product managers, the content spans IC to product management leadership—ideal if you’re stepping into new roles or scaling empowered product teams.
One of the most exciting evolutions is the Product Leadership Event, now a 1.5-day retreat. The format blends talk sessions, mini-workshops, dinners, and small-group excursions (boat rides, improv, etc.), giving leaders time and space to exchange playbooks, stress-test decisions, and build real relationships. It’s capped at 60 attendees (all in product leadership roles) to keep it intimate and useful. As someone who believes in outcomes vs output OKRs and first principles decision making, I appreciate how this structure encourages depth over breadth—and real accountability among peers.
Here are the core takeaways I’m carrying into my own planning: single-track means tighter curation, so every talk has to earn its place. Roundtables are growing into an “alternative track,” offering more ways to engage beyond stage talks. Workshops go deep and meet you where you are—IC, manager, or executive. And the leadership retreat expands to maximize learning from peers, not just from the stage. If you care about product discovery, product strategy, and conference networking that leads to actual business impact, this program looks thoughtfully engineered.
If you’re planning your 2026 calendar—or just curious how conferences evolve alongside the craft—this is a thoughtful walkthrough of what to expect. Come say hi to Teresa and Petra—on stage, at a roundtable, or somewhere in the hallway conversations that make these events memorable.
For more context and resources mentioned, explore: Product at Heart, Arne Kittler, Mind the Product, Christian Idiodi of Silicon Valley Product Group, Elaine Kasket, House of Beautiful Business, The 7 Habits of Highly Effective People by Stephen Covey, Rich Mironov, Marty Cagan, Claude Code, Codex by OpenAI, Marcus Castenfors, Büşra Coşkuner and her Success Metrics: A Playbook for Product Managers, Özlem Yüce’s Essential Toolkit for Product Managers, Petra’s Product Leadership Wheel (PLwheel), and Netlight.
Follow Teresa Torres: https://ProductTalk.org
Follow Petra Wille: https://Petra-Wille.com
Full transcripts are only available for paid subscribers.
I set out to create a lightweight, high-impact “Pendo Wrapped” experience for our users—and I did it in under 10 minutes with Pendo MCP. As a VP of Product Management, I’m constantly looking for fast, pragmatic ways to turn product insights into moments that drive engagement. This experiment was about transforming raw analytics into a concise, celebratory year‑in‑review that motivates customers to explore more value.
When I say “Pendo Wrapped,” I mean a simple, narrative-style summary of usage highlights: what got adopted, which moments mattered, and where value showed up most clearly. Framed well, that story reinforces product‑led growth by reminding users why they chose us, nudging them toward the next best action, and strengthening activation and retention without heavy development work.
My approach was straightforward: define a clear objective (celebrate milestones and prompt the next step), choose a focused set of metrics (adoption, engagement, and activation), and target relevant segments. Then I layered the narrative on top of existing analytics using in‑app guides and product tours to deliver the experience where it matters most—inside the product.
The reason it took minutes, not hours, is that Pendo MCP let me work with what we already had—segments, saved reports, and proven guide templates—so I could spend time on the story, not the scaffolding. No code, minimal configuration, and a crisp call to action made it feel polished without being heavy.
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.
If you want to replicate this quickly, start by selecting one user segment and three metrics that matter to them, write a two‑sentence narrative that connects those metrics to outcomes, and ship a short in‑app guide with a single, purposeful CTA. That’s enough to deliver a personalized year‑in‑review feel and spark immediate exploration—no new infrastructure required.
What surprised me most was how a small, story‑driven touch created outsized alignment across customers and internal teams. It turned analytics into advocacy, reminded our users of the value they’re already getting, and opened the door to deeper adoption. If you’re pursuing product‑led growth, a fast “Pendo Wrapped” is one of the highest‑leverage experiments you can run this week.
I’ve learned that the fastest way to lose customers with AI is to ship something powerful but unpredictable. The fastest way to earn their loyalty is to ship something powerful and trustworthy. That’s the job.
AI ethics in product management isn’t about theory anymore. It’s the line between trusted products and unpredictable ones. Here’s what PMs need to know.
When I frame AI ethics for my team, I translate principles into practices that protect customers and accelerate velocity. We bake trust into product strategy, delivery, and operations—so ethics is not a separate checklist, but a core capability that compounds over time.
First, I anchor the roadmap on explicit outcomes and guardrails. We set success metrics alongside ethical constraints, tying them to outcomes vs output OKRs, so teams know not only what to achieve but what to avoid. If a feature can’t meet our trust thresholds, it doesn’t ship—no matter how impressive the demo.
Data is where trust starts. We enforce data governance from day one: clear data lineage, collection minimization, role-based access, and privacy-by-design defaults. We document lawful bases for processing, consent flows, and retention policies, then automate checks so they run with every change—not just at launch.
On the model side, we use eval-driven development to turn subjective “looks good” into measurable quality. We design evaluations for safety, bias, robustness, and performance; we red-team prompts; and we test failure modes in realistic conditions. For LLMs, we lean on a retrieval-first pipeline to ground responses in authoritative data, and we apply context window management and prompt engineering patterns to reduce hallucinations.
In the product experience, we make ethical choices visible. That means clear disclosures when AI is in the loop, user controls to review and correct outputs, and transparent UX writing that avoids overclaiming. In-app guides and thoughtful tooltip design help users understand capabilities and limits without friction.
Shipping safely requires operational discipline. We build kill switches, human-in-the-loop overrides for high-risk actions, and incident playbooks that pair incident management with threat detection and response. SRE partnerships ensure observability covers both model behavior and customer impact, with rollback paths ready when drift or regressions appear.
Governance is a team sport. I maintain an AI risk register, review it with security, legal, and product trios, and brief leadership on residual risks and mitigations. Regulatory compliance isn’t a final hurdle; it’s a design input that shapes technical choices long before code reaches production.
Build vs buy decisions carry ethical implications too. Vendor due diligence covers model provenance, data handling, eval results, and incident history—not just feature checklists. Contracts codify SLAs, audit rights, and deletion commitments so our obligations to customers flow down the stack.
Finally, we earn trust in public. We publish model facts, change logs, and limitations in a customer-facing trust center, and we invite feedback loops that turn real-world usage into better safeguards. Stakeholder management matters here: being candid about trade-offs often increases confidence more than chasing perfection.
This is how I keep teams fast without being reckless: ethics as a product capability, not a poster. Build with intention, measure what matters, and make it easy for customers to understand, control, and benefit from your AI. That’s how we ship innovation that stays trusted—at scale.
Happy New Year! I’m kicking off 2026 with a behind-the-scenes look at what’s changing in my product practice, the experiments I’m running with my teams at HighLevel, and the trends I’m most energized by—especially around continuous discovery, AI workflows, and building stronger coaching cultures.
If you want to listen to the conversation that sparked many of these reflections, you can find it here: Spotify | Apple Podcasts.
Why Teresa sunset the live deep-dive cohorts—and how on-demand and the new Discovery Habits Toolbox better support real behavior change. This pivot resonated with my own experience: some skills, especially discovery habits, only stick when they’re reinforced in the flow of real product work, not just in a time-boxed cohort. In my org, we’re leaning into on-demand learning paired with manager coaching to drive durable behavior change.
What leaders actually need to coach interviewing, assumption testing, and core discovery habits inside their orgs. I’ve found that empowered product teams thrive when leaders have lightweight coaching tools, practical prompts, and clear expectations for product trios. This is less about one-off training and more about building communities of practice where deliberate practice and feedback loops become routine.
Why training is shifting toward ongoing, leader-supported learning (and how AI will accelerate the shift). AI Strategy isn’t just about tools—it’s about learning systems. For LLMs for product managers to create leverage, we need eval-driven development, privacy-by-design, and clear guardrails. I’m building AI workflows that enable managers to review interviews, spot anti-patterns, and nudge teams toward better decisions—without replacing critical thinking.
Teresa’s move into paid subscriptions and why AI content doesn’t fit the classic “design once, run for years” course model. I see the same reality in my content roadmap: the half-life of AI guidance is short. That pushes us toward subscription models, tighter feedback loops, and a more adaptive go-to-market strategy for education products.
A sneak peek into the AI tools Teresa is building for discovery work—from interview coaching to near-ready interview snapshot generation. I’m particularly excited by tooling that scaffolds better interviews, sharpens assumption testing, and speeds up synthesis without skipping the human judgment step. These capabilities map directly to where I want my teams investing time: spending less energy on admin and more on learning from customers.
Petra’s plans for the year: community building with Product at Heart, a new product leadership email course, her Product Leadership Wheel, and workshops launching in Cairo. As someone who believes in conferences as high-quality “energy wells,” I’m inspired by how these programs create momentum for leaders who are upgrading their coaching muscles.
The role of conferences and retreats in staying grounded, inspired, and connected. I treat these gatherings as strategic resets—spaces to test ideas, confront blind spots, and deepen my network for future collaboration. The best outcomes often come from serendipitous hallway conversations and hands-on sessions where you can pressure test frameworks with peers.
How Teresa is staying on top of academic research (and why “synthetic users” aren’t ready for prime time). I agree: while synthetic data can be useful for scaffolding, it’s not a substitute for direct customer contact. Combine academic rigor with real-world interviewing and strong data governance—especially when operating under General Data Protection Regulation (GDPR).
The shared challenge of evaluating vendors and conference speakers making questionable AI claims. My heuristic: ask for clear problem statements, reproducible evaluations, grounded benchmarks, and a path to safe deployment. If a pitch can’t show measurable uplift or ignores compliance, it’s not ready for empowered product teams.
Key takeaways I’m carrying into 2026: delivery models matter; leaders need coaching tools, not just training; AI is reshaping how we teach and learn; experimentation is the theme of 2026; and community still energizes. That’s the blueprint I’m using to strengthen continuous discovery, refine our AI workflows, and sustain high standards in product management leadership.
What about you? How are you integrating AI workflows into your discovery practice, and what coaching tools are helping your managers reinforce the right habits? Share your approach—I’d love to learn what’s working in your context.
Resources & Links:
Follow Teresa Torres: https://ProductTalk.org
Follow Petra Wille: https://Petra-Wille.com
Teresa’s website: Product Talk
General Data Protection Regulation (GDPR)
Product Talk Academy
Deliberate Practice – ATP episode where Teresa talked about the ending live cohorts for Deep Dive classes
2026 is closer than it feels, and the signals are already clear. I’ve been synthesizing what I’m seeing across empowered product teams, boards, and cross-functional partners into a practical view of what matters next. A sharp look at product management trends for 2026. Not guesses, but signals from top product leaders shaping how PMs will actually work next.
In this analysis, I distill eleven shifts that are changing the craft—from outcomes vs output OKRs and continuous discovery to stronger product strategy and tighter product roadmapping and sprint planning. The throughline is simple: prioritize customer value, ship with focus, and measure what moves the business. These aren’t headline trends; they’re working patterns I’m seeing across high-performing organizations.
AI is no longer a side project—it’s part of the product manager’s core toolkit. Agentic AI, LLMs for product managers, and trustworthy AI workflows are accelerating discovery, sharpening problem framing, and enabling faster iteration. The best teams pair this with disciplined evaluation and experimentation, so insight compounds without sacrificing safety, privacy, or product quality.
Execution is getting crisper through product trios and stronger stakeholder management. When design, product, and engineering co-own discovery and delivery, teams reduce handoffs and increase clarity. That alignment translates into better prioritization, fewer context-switches, and a roadmap that reflects real trade-offs—not wish lists.
On growth, product-led growth remains a durable engine when it’s anchored in a compelling value proposition and instrumented end-to-end. Clear activation moments, in-app guides, and thoughtful product tours outperform brute-force acquisition. When we connect these motions back to product strategy and the roadmap, we create a repeatable loop that compounds adoption and retention.
Governance and trust are now table stakes. Privacy-by-design, data governance, and a pragmatic approach to regulatory compliance protect both users and velocity. Teams that build these practices into their operating model move faster because they avoid late-stage rework and maintain stakeholder confidence.
If you’re leading a product org—or aspiring to—this is your field guide to 2026. I’ll unpack where these shifts are strongest, how to apply them in your context, and the pitfalls to avoid. The aim is to give you clear language, concrete practices, and a sharper edge as you shape what your team builds next.
