Tag: product management leadership

25 High-Impact Career Paths for Software Engineers Beyond Coding: My Real-World Playbook

I’ve spent years helping talented engineers explore what’s next when pure coding no longer feels like the only—or best—path. From hiring across cross-functional teams to mentoring career pivots, I’ve seen firsthand how engineering strengths translate into high-leverage roles that shape product, strategy, and growth.

Software engineers have alternative career options leveraging their skills in roles like product manager, data scientist, business analyst, and 22 more.

When an engineer moves into product management, they’re not starting from scratch—they’re redirecting problem-solving, systems thinking, and customer empathy toward outcomes. In practice, that means mastering product discovery, strengthening stakeholder management, and getting fluent in product roadmapping and sprint planning, so decisions are guided by impact rather than “outputs vs outcomes” confusion. I’ve watched this transition unlock empowered product teams and clearer prioritization across complex backlogs.

Data-oriented paths are equally compelling. If you enjoy experimentation and evidence-based decisions, roles in analytics or data science reward rigor. Think A/B testing, identifying the minimum detectable effect (MDE), and using tools like Amplitude analytics to translate behavioral signals into product bets. Pair that with retention analysis and you’ll become indispensable to growth conversations.

Business-facing roles such as business analyst or product marketing manager are ideal if you’re energized by customer problems and market narratives. Your engineering fluency sharpens value propositions, product positioning, and go-to-market strategy in a way that resonates with both buyers and builders. In my teams, the best bridges between product and revenue often came from former engineers who could articulate trade-offs with clarity.

If operational excellence is your edge, consider SRE, DevOps, or cybersecurity. The same instincts that push you toward clean CI/CD pipelines and resilient architectures translate well into incident management, threat detection and response, and privacy-by-design practices. These roles reward systems thinking and the ability to balance reliability with delivery speed.

For engineers who love community and storytelling, developer evangelism is a natural fit. You’ll translate complex concepts into actionable guidance, from in-app guides and product tours to UX writing and documentation. The best evangelists I’ve worked with turn feedback loops into product insight, strengthening activation and product-led growth without heavy sales pressure.

Customer-facing technical roles—solutions engineer, forward deployed engineer, or technical consultant—let you stay close to the product while solving real-world problems. You’ll drive onboarding quality, user activation, and adoption while surfacing insights that influence roadmaps. Done well, this work tightens the loop between customer outcomes and product decisions.

AI-centered roles are expanding rapidly. If you’re curious about AI Strategy, retrieval-first pipelines, or the practical use of LLMs for product managers, you can bring an engineer’s discernment to a noisy space. The most valuable contributors here pair pragmatic architecture choices with clear risk management and measurable business value, not hype.

Leadership tracks remain a strong option too. The IC to manager transition isn’t about title; it’s about raising the ceiling for others. You’ll coach empowered product teams, shape organizational development, and align initiatives to defensible metrics—think DORA metrics for flow, leading indicators for value, and OKRs that measure outcomes over output.

If you’re exploring a pivot, start small and intentional. Run “career A/B tests” by taking on cross-functional projects, shadowing adjacent roles, or shipping a lightweight portfolio that demonstrates the new muscle. Join a ProductCon session, practice conference networking, and refine a narrative that links your engineering foundation to the outcomes your target role owns.

Finally, map your personal unfair advantages—domain knowledge, systems thinking, customer empathy, or operational rigor—to the roles that value them most. With focus, you can reposition your engineering experience into a differentiated story that accelerates your next chapter. The breadth of options is real, and with a deliberate plan, you’ll turn curiosity into conviction—and conviction into impact.

Inspired by this post on Product School.

November 24, 2025
Mastering Data Governance in the AI Era: Move Fast, Reduce Risk, and Unlock Trusted Insights

Every week, I’m in conversations with product leaders, engineers, and security teams who are trying to ship AI features faster without compromising trust. The tension is real: stakeholders want velocity, customers want transparency, and regulators want accountability. That’s exactly where modern data governance earns its keep.

New AI pressures are redefining what good governance takes. Learn how to build better frameworks, move fast with confidence, and keep your data from being a black box.

In my role leading product management, I’ve learned that robust data governance isn’t a compliance checkbox—it’s a strategic capability. When we treat governance as a product, we architect for clarity, safety, and speed. That means aligning AI Strategy with day-to-day delivery so teams know what they can ship, when, and why.

Here’s the practical blueprint I rely on. First, establish ownership and a shared language. Create a living data catalog, lineage maps, and clear data classifications so teams know which assets are sensitive, regulated, or eligible for training LLMs. Second, harden privacy-by-design and least-privilege access. Bake PII detection, secrets management, and role-based policies directly into your workflows. Third, bring quality and observability to the forefront: instrument data contracts, monitor drift, and track model performance across environments. Finally, implement model governance end to end—dataset cards, model cards, bias testing, human-in-the-loop review, and a repeatable evaluation harness.

To move fast with confidence, make governance invisible and automated. Treat policies as code in CI/CD, gate deployments with pre-merge checks, and fail builds that violate data contracts. Log prompts and outputs responsibly, route unsafe patterns to red-teaming, and use a retrieval-first pipeline to anchor models on verified sources rather than fragile context stuffing. This is how we scale AI product development while keeping audit trails complete and costs in check.

Avoiding the black-box problem starts with transparency. Document assumptions, training data sources, and known limitations—then expose explanations where it matters in the product experience. Pair this with a unified analytics platform to tie telemetry, feature flags, and user feedback to model changes. When something goes sideways, your observability, incident management playbooks, and threat detection and response processes should make root-cause analysis fast and defensible.

If you’re building your program from scratch, use a 30-60-90 approach. In the first 30 days, inventory systems, classify data, and map high-risk use cases. By day 60, formalize RACI for governance, deploy access controls, and set up your evaluation pipeline with golden datasets and measurable acceptance thresholds. By day 90, operationalize incident response, conduct tabletop exercises, and wire governance outcomes into OKRs—think time-to-approval for high-risk changes, reduction in production incidents, and model evaluation pass rates.

This playbook pays off in board conversations and with customers. You can articulate your AI risk management posture, show measurable progress on regulatory compliance, and demonstrate how governance accelerates—not hinders—delivery. Most importantly, your teams gain the confidence to experiment, knowing there’s a safety net that protects users, the brand, and the business.

If your organization is wrestling with how to balance innovation and control, start small, codify what works, and scale with intent. With the right foundations in data governance, AI becomes an engine for durable advantage—not a source of sleepless nights.

Inspired by this post on Amplitude – Perspectives.

November 21, 2025
How We Built an AI Sleep Coach: CBTI, Voice AI, and a Product Playbook for Better Rest

What if your morning started with a helpful check-in from a voice AI that actually improves your sleep—using the same core principles that typically cost thousands of dollars and come with year-and-a-half waitlists? That idea energizes me as a product leader, because it blends clinical-grade outcomes with consumer-grade accessibility. Recently, I dug into how the team at Rest built an AI sleep coach inspired by Cognitive Behavioral Therapy for Insomnia (CBTI), and why their method offers a repeatable blueprint for complex, personal AI products.

The origin story is a classic product discovery moment. Rest’s team noticed that a meaningful slice of users in their podcast app were using audio to fall asleep. Although it represented only about 10% of users, that group showed a high willingness to pay. That signal pushed them to explore a dedicated sleep solution, moving from a general audio app to a targeted sleep experience—and eventually toward an AI-powered coach as LLMs matured.

Through jobs-to-be-done research, they identified a clear, underserved segment: “DIY sleep hackers.” These are motivated users who want agency, structure, and results without navigating clinical systems. Choosing CBTI (a clinically proven approach with 80% efficacy) gave the product a strong evidence-based foundation while remaining accessible as a wellness tool. It’s the kind of strategic choice I look for: credible, measurable, and aligned with user motivation.

The product evolution moved in smart, incremental steps. Rest started with a basic text chatbot before graduating to a voice-first experience—using Vapi for voice and OpenAI for reasoning. Voice changed the relationship dynamic: it increased intimacy, lowered friction for daily check-ins, and made behavioral coaching feel human without pretending to be. The team built a memory system that tracks context (like traveling or having a dog) with time-based relevance, which keeps conversations fresh, respectful, and genuinely personalized.

Daily engagement is driven by dynamic agendas that adapt based on sleep data, the user’s stage in the program, and their recent compliance. I love this mechanic: it operationalizes behavior change by sequencing the right intervention at the right time. In parallel, they developed text via OpenAI Assistants while building voice with Vapi, which let them ship value while learning in two modes. They also moved from massive system prompts to RAG for general sleep knowledge, keeping personal user context in the prompt—reducing brittleness while improving scalability.

Because sleep sits close to healthcare, the team drew a firm line between wellness and medical positioning. They implemented clear guardrails: no diagnosis, no medication advice, and strong boundaries on scope. Weekly error analyses with domain experts (sleep therapists) tightened quality and tone, and they adopted LLM-powered evals to enforce safety boundaries. For observability and evaluations, they leveraged Langfuse, and they experimented with Hamming for voice testing to refine the experience end-to-end.

Under the hood, this is a great example of “one bite of the apple at a time” product building in AI. Start with a simple interface, anchor on an evidence-based method, layer personalization with memory, formalize program structure with dynamic agendas, and shift to RAG when general knowledge outgrows prompt engineering. As a product leader, I see strong echoes of agentic patterns here—goal-oriented orchestration, stateful memory, and adaptive planning—shipped in pragmatic increments rather than as a monolithic platform rewrite.

A few takeaways I’m applying with my teams: First, segment deeply and pick a high-intent niche (those “DIY sleep hackers” were the right beachhead). Second, let modality fit the job—voice is not a gimmick when it boosts compliance and empathy. Third, design safety and scope from day one if you’re anywhere near health. Finally, invest early in evals and observability so you can improve with confidence, not hope.

If you want to explore the full conversation and product decisions, you can listen here: Spotify | Apple Podcasts.

Resources & Links:

Rest – AI sleep coach app

Vapi – Voice agent platform Rest uses

Langfuse – Observability and evals platform

Hamming – Voice testing platform

AI Evals Maven Course by Hamel Husain and Shreya Shankar

Bottom line: Rest demonstrates how to take a clinically grounded method like CBTI, translate it into a daily voice-first experience, and ship it with rigor. If you’re building in AI, this is a model worth studying—practical, safe, and deeply user-centered.

Inspired by this post on Product Talk.

November 20, 2025
High-Quality Data, High-Velocity AI: My Product Playbook for Governance, Trust, and Scale

Every breakthrough we ship in AI reinforces a simple truth I live by: "Companies that prioritize data quality, governance, and structure will accelerate their AI initiatives the fastest." That statement captures the difference between flashy demos and durable, scalable products. In my experience, the strongest AI Strategy starts with the discipline to treat data as a product, not an afterthought.

When teams rush to production with generative AI or LLMs, the first issues rarely come from the model itself—they come from the data. Poor lineage leads to hallucinations, inconsistent schemas inflate costs, and weak access controls erode trust. For LLMs for product managers, this is the gap between a compelling prototype and a reliable system customers depend on every day.

Let me clarify what I mean by data quality, governance, and structure. Quality is completeness, accuracy, freshness, and consistency across sources. Governance is policy, ownership, and accountability—privacy-by-design, regulatory compliance, and AI risk management built in from day one. Structure is the architecture: clear data contracts, standardized schemas, metadata and lineage, and role-based access that keeps sensitive signals protected while enabling speed.

Here’s the product playbook I use to operationalize this. First, map critical sources and define data contracts at the edges so producers and consumers can move independently. Second, standardize schemas and entity resolution to eliminate ambiguous joins. Third, enforce privacy-by-design with policy-as-code and automated redaction. Fourth, converge analytics into a unified analytics platform so definitions, freshness, and observability are shared. Fifth, instrument end-to-end lineage and quality SLAs with alerting. Finally, close the loop with human feedback and labeling to continuously improve model performance.

For generative AI workloads, a retrieval-first pipeline is essential. Unify trusted sources (product analytics, CRM, support, docs), embed and index them with guardrails, and focus on context window management to keep prompts lean, relevant, and cost-effective. This approach improves response quality, reduces token spend, and makes updates near-real-time—without retraining the base model every week.

Measure what matters. Tie model outcomes to product metrics through rigorous A/B testing, and size experiments with minimum detectable effect (MDE) so you can ship confidently. Use product analytics to verify that better data actually improves activation, retention, and support deflection. When teams can trace an AI improvement back to a specific data-quality fix, they invest in governance with conviction.

Culture closes the gap. Empowered product teams and product trios (PM, design, engineering) make crisper decisions when data stewards are embedded and accountable. Clear ownership, shared definitions, and transparent dashboards reduce friction with security and compliance while speeding up delivery. This is how product management leadership sustains velocity without trading away trust.

The bottom line: if we want faster, safer, and more scalable AI, we start with the data. Build strong foundations, treat governance as enablement, and structure every step so improvements compound. With that in place, Generative AI stops being a science experiment and becomes a durable competitive advantage.

Inspired by this post on Amplitude – Perspectives.

November 19, 2025
Scaling 16 ‘Startups Within a Startup’: My Enterprise GTM, PMF, and Sales Hiring Playbook

I’ve long believed the most resilient software companies master two hard things at once: they move decisively from mid-market to enterprise, and they ship multiple “best-of-breed” products without losing focus. The operating model that makes this possible — running 16 “startups within a startup” — resonates with how I build product organizations. In this piece, I’m unpacking the frameworks I use to make that model work at scale, from “product-market-sales fit” to capacity-driven go-to-market.

Why do companies get stuck in the mid-market? In my experience, it’s rarely just sales execution. It’s usually a product readiness gap hiding inside a distribution story. Enterprise customers expect battle-tested architecture, deep security and compliance, robust RBAC, data governance, audit trails, and predictable SLAs. They also expect a clear value proposition, strong references, and a crisp “who do we beat and why” articulation. If any one of those is fuzzy, your deals elongate or disappear. The fix starts by designing intentionally for enterprise and mid-market from day one: plan for scale, extensibility, change management, and procurement complexity — then validate with lighthouse customers, not just friendly pilots.

Sometimes the hardest enterprise move is saying no. I’ve advised teams to walk away from a marquee logo like Netflix when the requirements force unnatural acts that derail your roadmap. It feels counterintuitive — especially when the logo is irresistible — but your ideal customer profile must govern priorities. Your long-term velocity compounds when you align deeply with the customers who value your native strengths.

I differentiate between “product-market-fit” and “product-market-sales fit.” The former tells me a product delivers undeniable value; the latter tells me my distribution system can reproduce that value at scale. I watch for signals beyond anecdotes: win rates by segment, cycle time, ramp time to first deal, multi-threading depth, net revenue retention, and the percentage of customers who expand within two quarters. When these lag, I diagnose whether I have a product problem (insufficient value or clear “must-have” outcomes) or a distribution problem (positioning, enablement, or segmentation). The diagnosis determines whether I ship features, sharpen messaging, or rewire the motion.

On go-to-market, I build a capacity-driven machine instead of chasing deals. That means matching pipeline health to quota capacity, calibrating territories to intent density, and instrumenting enablement so new reps reach productivity with consistent talk tracks and crisp objection handling. I prefer simple, repeatable plays that compound: a precise ICP, strong proof packages, and a pricing model that meets customers where they are. When those are humming, founder-led GTM transitions smoothly to a scalable sales engine without losing the product’s original edge.

Hiring your first head of sales is a leverage point. I look for four things: pattern recognition in my specific segment, a builder’s mindset (process and playbooks without bureaucracy), rigorous pipeline hygiene, and the ability to partner with product on “where we win and why.” In the interview, I run scenario loops: how they’d disqualify non-ICP deals, how they’d recover a late-stage stall, how they’d deliver the first 90 days plan, and how they’d coach to a consistent message. Early founders absolutely need to learn sales — not to become the forever closer, but to encode customer truth into the product and the motion.

Strategic timing matters, too. There’s a well-known case of selling three days pre-IPO; whether or not you’d make the same call, the lesson stands: market timing, certainty of outcome, and board alignment are strategic variables, not afterthoughts. A healthy board brings independent thinking, timely guidance on capital and risk, and a unified narrative — especially when the market is volatile.

On competition, I pressure-test our narrative around points of parity and a “binary differentiator.” In crowded markets, incremental advantages don’t move the needle. You need one thing customers can’t ignore — faster time-to-value, a step-function in accuracy, or a cost curve that resets the category. I ask every team to prove a binary outcome: if we’re in the eval, there’s a clear, testable reason we win.

Launching multiple products simultaneously demands ruthless clarity. I structure the org as “startups within a startup,” each with its own GM, product roadmap, and GTM targets, but anchored to a shared platform for identity, data, and extensibility. Product managers operate as mini-entrepreneurs — owning P&L-like metrics, customer outcomes, and crisp product positioning — while a central platform team ensures consistency and speed. The rallying cry across these teams is simple: “We need to be best of breed.” If a product can’t credibly win on its merits, we either sharpen it until it does or we stop investing.

Execution lives in the details. I emphasize outcomes vs output OKRs, product trios for tight alignment, and continuous improvement powered by CI/CD so we can learn faster. We track DORA metrics like deployment frequency to ensure our cadence supports enterprise reliability. Weekly operating reviews focus on value delivered: have we solved the customer’s core job, and can our sales and success teams prove it with repeatable stories? When the answer is yes, expansion follows naturally.

Bringing it all together: moving upmarket, building “product-market-sales fit,” and running 16 product lines under one roof is achievable with the right structure and discipline. Design for enterprise from the start, let your ICP guide every trade-off, anchor GTM in capacity and repeatability, hire sales leaders who build with you, enforce a “binary differentiator,” and empower product managers as owners. Do that, and the “startups within a startup” model becomes a force multiplier — not just a slogan.

November 19, 2025
UX Product Manager Playbook: Master the Design-PM Overlap and Fast-Track Your Career

I’ve spent years leading product organizations where the best outcomes emerged from a tight handshake between design rigor and product strategy. The role that consistently sits at that high-impact intersection is the UX product manager. Done well, it’s the engine of product-led growth: deeply empathetic with users, relentlessly focused on outcomes, and fluent in both discovery and delivery.

Curious about the UX product manager role? Discover how it overlaps with design, PM, and why it might be the next step in your career.

At its core, a UX product manager owns the customer experience end-to-end while steering the business toward measurable outcomes. I translate user insights into prioritized problems, shape the solution space with designers and engineers, and validate decisions with data. Unlike a traditional PM who may skew toward market sizing and business cases, or a designer who may emphasize interaction patterns and visual systems, I integrate both frames to ensure we ship experiences that users adopt, retain, and recommend.

On the design side, I work hand-in-hand with product designers and UX writing to define the problem, craft flows, and stress-test usability. I obsess over clarity, affordances, and friction—especially during onboarding. Strong UX writing often makes or breaks first-run experiences, and I treat microcopy as part of the product, not an afterthought.

On the product management side, I anchor teams on outcomes vs output OKRs, facilitate product discovery, and drive prioritization against clear value propositions. I operate within empowered product teams and build tight product trios with design and engineering so we can validate assumptions fast, reduce waste, and increase the surface area for innovation.

Day-to-day, my craft blends qualitative research and quantitative analysis. I lean on tools like Amplitude analytics, Pendo, and Intercom to instrument funnels, run A/B testing, and perform retention analysis. When I experiment, I’m explicit about the minimum detectable effect (MDE) to avoid inconclusive reads. I measure the impact of changes on activation, time-to-value, and core feature adoption—and I make sure we can trace improvements to specific user segments.

User activation is my early warning system. If activation is lagging, I revisit the first-mile experience: guidance, progressive disclosure, in-app guides, product tours, and contextual tooltip design. I also ensure our onboarding is sequenced around the critical path to value rather than a feature parade. When activation improves, downstream KPIs like retention and expansion usually follow.

If you’re looking to become a UX product manager, start by strengthening three pillars: customer insight, product strategy, and experience design. Build a habit of continuous product discovery—co-creating with users, running lightweight experiments, and synthesizing findings into actionable decisions. Learn to translate insights into a product roadmapping and sprint planning cadence that energizes the team and keeps stakeholders aligned.

Your portfolio should read like a decision journal, not a gallery of screens. For each case study, frame the problem, outline constraints, describe alternatives considered, and show the experiments you ran. Include the metrics that mattered (activation, adoption, retention), the instrumentation you used, and the decisions you made when data was ambiguous. Hiring managers want to see your thinking under uncertainty and how you rallied cross-functional partners.

Communication and stakeholder management are differentiators. I tailor narratives for executives (trade-offs and business impact), for engineers (clarity on constraints and sequencing), and for design (user jobs, heuristics, and the narrative arc of the experience). Clear, frequent updates keep momentum high and reduce thrash, especially when priorities shift.

On the execution side, I make sure delivery never drifts from discovery. Every sprint is tied to a learning goal or outcome. We pair quick prototypes with production experiments, and we celebrate killing ideas that don’t move the needle. That discipline keeps us focused on outcomes and accelerates iteration speed without sacrificing quality.

Finally, a few career accelerators: get comfortable with analytics, learn the language of UX writing, practice story-based demos, and go deep on onboarding patterns. If you can move activation, you can change the trajectory of the business. Pair that with a strong perspective on product-led growth and you’ll be ready to lead product work that compounds.

The UX product manager role is a force multiplier. It’s where rigor meets empathy, and where design and PM converge to create experiences customers love—and businesses rely on. If that intersection energizes you, you’re already on the right path.

Inspired by this post on Product School.

November 19, 2025
Intercom is now a Shopify Plus Technology Partner: AI-powered support to scale ecommerce

I’m thrilled to share that Intercom is now a certified Shopify Plus Partner on the Technology Track. As someone who obsesses over product quality, speed, and measurable outcomes, this milestone reflects the rigorous standards we hold ourselves to and the trust Shopify Plus merchants can place in our solution.

The Shopify Partner Program Technology Track supports the largest Shopify merchants by helping them find the apps and solutions they need to build and scale their business. The program is available specifically for Shopify Partners who provide a level of product quality, service, performance, privacy, and support that meets the advanced requirements of Shopify Plus merchants.

As a Technology Partner, Shopify has recognized Intercom as a provider trusted to help high-growth ecommerce brands scale.

“The Shopify Partner Program Technology Track is designed to meet the advanced requirements of the world’s fastest growing brands. We’re happy to welcome Intercom to the program, bringing their insight and experience in Customer Support to the Plus merchant community.”

— Jeff Kennedy, Head of Product Partnerships, Shopify

For Shopify Plus merchants, this certification means that our integration is vetted and optimized, and that our roadmap aligns with Shopify’s priorities. In practice, that translates into faster resolutions, less context switching, and more personalized conversations—without compromising privacy or performance.

Over the past year, we’ve launched a series of enhancements to our Shopify integration to give merchants more control and speed in support, including:

Data Connector templates so our AI Agent Fin can fully resolve requests from customers who want to get information about their Shopify order.

Multi-store support for merchants to manage conversations from multiple storefronts in one inbox.

Inbox order actions for merchants to take actions like editing shipping addresses, cancelling and refunding whole orders, deduplicating or creating duplicate orders based on existing ones, all without leaving the conversation.

EU workspace support to ensure merchants stay aligned with EU data residency requirements.

Launch your AI customer service faster—this hero graphic invites users to try the #1 AI agent with a bold headline and clear CTA, emphasizing practical, real‑world demos over polished Hollywood sizzle.

Updated data mapping and custom fields to keep Shopify order data and customer profiles fully in sync.

These updates make it faster and easier for merchants to resolve queries, personalize conversations, and drive loyalty, all from one platform. I’ve seen these capabilities reduce average handle time and minimize escalations—especially for complex order changes and post-purchase workflows.

We’re already seeing how our Shopify integration is helping merchants scale their support and deliver better customer experiences: teams are deflecting routine inquiries with AI while empowering agents to focus on high-value, relationship-building conversations.

Our team is continuing to invest in Shopify-specific capabilities. Here’s what we’re working on:

Expanded Fin Tasks for complex order actions with new pre-built workflows.

Enabling Model Context Protocol (MCP) support.

Smarter product search powered by Shopify data.

These additions will help merchants resolve faster, personalize at scale, and stay ahead of rising customer expectations – particularly as we approach peak season. We’ll continue to ship in tight feedback loops with Plus merchants to ensure each improvement moves the needle.

If you’re a Shopify Plus merchant, learn more about how we can help you scale your support with Fin, the best performing AI Agent for ecommerce. Ready to move fast? Get started with Fin now.

Inspired by this post on The Intercom Blog.

November 18, 2025
How I’m Rebuilding Customer Service for 2026: An AI‑First Playbook for Real Impact

Like many support leaders right now, I’m deep in 2026 planning. The more I map scenarios and stress-test assumptions, the clearer one thing becomes: the way work gets done has fundamentally changed, and that change must reshape our customer service organization.

In 2026, you won’t get the full value of AI by keeping your org chart, systems, and operating model the same. You need to think differently about how support is structured, how performance is owned, and how your systems evolve around an AI-first model. That’s the lens I’m using across my team and our cross-functional partners.

To help you do the same, I’m launching a 2026 customer service planning series. Over the next five weeks, I’ll share how I’m approaching roles, skills, organizational design, and an operating model that makes AI the backbone of support—not a bolt-on feature.

We’ll publish each edition here and on LinkedIn. If you’d rather get them by email as soon as they go live, drop your details and I’ll send each edition straight to your inbox.

But before you can make any of those decisions, you need the right mindset and the right internal conditions for change. That’s where I’m starting this week.

Week 1: Start with a mindset shift

If you were building support from scratch today, you’d design around AI from day one. That’s the mindset to carry into 2026—and it’s the mindset I’m using to guide investment and accountability.

Too many teams still treat AI like a feature instead of infrastructure. They tack it onto existing processes, limit scope to tier-one issues, and never evolve the organization or systems around it. I’ve seen that approach stall progress and fragment the customer experience.

Those teams are thinking too small. They chase incremental efficiency, underinvest in the system change required to make AI successful, and get stuck. The result: a reactive team, a choppy customer experience, and value left on the table.

AI Agents are fully capable, end-to-end resolution engines. They fundamentally change the architecture of support.

To plan effectively and get the most value out of the technology, you need to adjust your mental model. Here are the mindset changes I’m prioritizing.

1) Move from ‘AI as a tool’ to ‘AI as infrastructure’

For the past decade, support systems have been the intermediary between customers and human support agents. AI isn’t an intermediary, it’s the first touchpoint (and often the last), the primary resolver, it manages workflows, orchestrates handoffs, and takes real actions.

Planning with the “AI is a tool” mindset leads to small optimizations that don’t move the needle. Planning with the “AI is infrastructure” mindset lets you redesign around the real sources of value creation.

Here’s what I’m designing around in 2026:

• Clear ownership of Agent performance

• A feedback loop that never shuts off

• A shared understanding of when humans step in

• Systems that evolve as AI capabilities expand

This framing sets up every decision that comes later in your planning process.

2) Look at how the work is changing

You need to plan your 2026 support organization around what the distribution of work will be—not what it is today. AI has shifted where volume goes, what humans spend time on, where judgment is needed, how performance is measured, and how the customer experience is designed.

If your planning assumes the current distribution is stable, you’ll design the wrong structure. I’m modeling for the work that’s coming, not just the work on our queue today.

3) Think like a product leader

When customers primarily interact with your AI Agent, support becomes responsible for designing the customer experience—not just managing it.

“Support is becoming a product function, and you are becoming a product leader”

Design your 2026 support org for AI from day one. This Gamma testimonial shows how an AI agent (Fin) resolves 80%+ of inbound requests, letting a small team scale customer service efficiently without increasing headcount.

Support is now a product surface, and support teams act like AI product teams. They:

• Design the customer experience

• Create and curate the knowledge layer that drives AI quality

• Maintain continuous improvement loops and tune system behavior over time

This is a big shift. Your planning—hiring, skills, rituals, and metrics—needs to reflect that evolution.

4) Redefine performance

This is a big mental leap for support leaders. Traditional performance was measured on speed and satisfaction, but AI performance is measured on resolution, impact, and system reliability.

Planning for 2026 means assuming that:

• Humans will handle a smaller % of volume.

• Customer experience will be shaped by AI’s performance, not throughput

• “Support productivity” gets measured differently

When AI handles the bulk of your support volume, you need new metrics for how your team creates value. In practice, that means instrumenting AI and human-in-the-loop workflows with the same rigor you’d apply to a customer-facing product.

5) Understand that your value increases as AI takes on more work

You need to re-orient your team around AI’s performance to get the most value out of it. The more complex work you give it, the higher impact it will have.

Instead of routing complex, messy questions straight to your human team, shift their focus to improving the AI system so it can take on more over time.

Automating low-effort questions reduces noise, but automating complex workflows changes the economics of your entire team. It creates asymmetric returns that compound as AI absorbs the work that once demanded the most time and skill.

6) Plan for adaptability

A big difference between traditional planning and 2026 planning is simple: change will be constant.

“Change is hard, but the teams that adapt will be the ones who get the most out of this opportunity”

AI learns, evolves, and improves continuously. I’m asking, “How do we build an organization designed to adapt fast as the system evolves?” That question is informing everything from team topology to knowledge governance and experimentation cadence.

Food for thought

Heading into 2026, your org chart will look different—and that’s a good thing. Your people will play new, more meaningful roles as designers, curators, and stewards of an AI-first customer experience.

Once you accept that 2026 demands a different way of thinking, working, and planning, you can move to the next stage: designing the support organization that fits this future. I’ll share exactly what that looks like next week, including roles, skills, and ownership models that have worked well in my experience.

Want the full series delivered by email? Drop your details and I’ll send each edition to your inbox as soon as it’s published.

Inspired by this post on The Intercom Blog.

November 18, 2025
From KPIs to Comebacks: How I Lead Through Setbacks with Curiosity, Care, and Discovery

Setbacks are the tax we pay for doing meaningful product work. As a VP of Product Management, I’ve learned that what separates resilient teams from the rest isn’t a lack of failures—it’s how we metabolize them. This episode of All Things Product with Teresa Torres and Petra Wille is a powerful reminder that recovery, reflection, and rigorous product discovery are as essential as speed and execution.

Listen to this episode on: Spotify https://open.spotify.com/episode/10LYRya7boYJBHTYBnE79E?ref=producttalk.org | Apple Podcasts https://podcasts.apple.com/kh/podcast/dealing-with-setbacks/id1794203808?i=1000737190520&ref=producttalk.org

What struck me most is how Teresa shares a deeply personal story about her long recovery from an injury—and how that journey mirrors the nonlinear reality of product development. In product, just like in healing, progress is rarely a straight line. We have surges, stalls, and moments that feel like reversals. Yet with the right mindset and rituals, we still move forward.

Professionally, we all face moments when your product fails to move a single KPI, when a launch falls flat, or when you just feel stuck. I’ve been there—in quarterly reviews, post-launch standups, and board prep. The instinct is to sprint straight into solutions. The wiser move is to respond with curiosity, emotional honesty, and resilience, then re-engage our discovery habits with intention.

If you’re a PM, designer, or researcher, consider this an invitation to rebalance. Recovery and reflection are just as important as velocity and success. That’s not soft talk—it’s how empowered product teams build durable performance without burning out.

On the emotional reality of setbacks, I’ve learned to normalize naming the loss. We put immense pressure on ourselves, and it’s okay (and necessary) to grieve product failures. When we acknowledge the disappointment, we regain the ability to observe clearly—and to learn.

Leaders play a crucial role here. I create space for teams to recover before jumping into post-mortems. We don’t whiteboard over feelings; we schedule time for decompression, then conduct a crisp, blameless review. That sequencing transforms the quality of insights and strengthens psychological safety.

Another lesson that resonates is the danger of tying performance too tightly to outcomes. Outcomes matter, but they are lagging indicators influenced by many externalities. I evaluate performance on behaviors: clarity of problem framing, rigor in discovery, quality of decision-making, and stakeholder alignment. This aligns with outcomes vs output OKRs and keeps us focused on controllable excellence.

How do we build resilience? Continuous discovery builds resilience by normalizing failure. When we test assumptions routinely with customers and data, we turn large, risky bets into a series of small, learnable steps. Teams recover faster because failure becomes feedback—frequent, cheap, and informative.

For perspective, I often use the 10–10–10 framework (from Decisive by Chip & Dan Heath). I ask: How will this setback feel in 10 minutes, 10 months, and 10 years? The answers de-escalate urgency, expand our time horizon, and produce better, calmer decisions.

Here are the key takeaways I’m carrying forward. Setbacks are not just inevitable—they’re part of doing meaningful product work. Giving teams time and space to process failure builds long-term resilience. Mourning losses is just as important as celebrating wins.

Healthy discovery cultures embrace reflection, psychological safety, and emotional honesty. And most importantly, staying consistent with discovery habits helps teams recover faster and learn more deeply.

Notable moments that stood out for me include: [00:02:00] Teresa shares the story of her injury and what it’s taught her about patience and setbacks. The parallel to product cadence is both humbling and motivating.

[00:10:00] Petra talks about a team whose carefully planned launch didn’t move a single KPI. I’ve led similar debriefs; when we anchor on customer insight gaps rather than blame, the next iteration improves dramatically.

[00:20:00] Discussion on allowing space for grief and frustration after failure. In my teams, we time-box “emotional processing” before we enter analysis mode—it humanizes the work and sharpens the learning.

[00:30:00] Why organizations must decouple performance reviews from short-term outcomes. I align evaluations to strategy execution quality, hypothesis discipline, and cross-functional collaboration.

[00:40:00] How continuous discovery can help teams normalize—and even learn to appreciate—setbacks. When discovery is weekly, momentum becomes self-healing.

If you want to dig deeper, here are useful links from the episode. Follow Teresa Torres: https://ProductTalk.org

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

Mentioned in the episode: Decisive by Chip & Dan Heath — The 10–10–10 framework for perspective in decision-making https://heathbrothers.com/books/decisive/?ref=producttalk.org

Teresa Torres’ Continuous Discovery Habits — Building resilience through ongoing discovery practices. https://www.amazon.com/Continuous-Discovery-Habits-Discover-Products/dp/1736633309?dchild=1&keywords=continuous+discovery+habits&qid=1621385051&sr=8-2&linkCode=sl1&tag=teresatorres-20&linkId=34bc439ac78da06e1398f7bf069b219e&language=en_US&ref_=as_li_ss_tl&ref=producttalk.org

Join the Conversation: Have thoughts on this episode? Leave a comment below. I’d love to hear how you create space for recovery while sustaining product velocity.

Full Transcript: Full transcripts are only available for paid subscribers.

Inspired by this post on Product Talk.

November 18, 2025
How I Use ChatGPT to Supercharge PM: Smart Workflows, Killer Prompts, and Real-World Wins

Every week, I lean on ChatGPT to cut through noise, reduce rework, and move faster with more confidence. It’s not a silver bullet, but it has become an unfair advantage in my day-to-day leadership of product strategy, discovery, and delivery. Unlock workflows, prompts, and real PM tips showing how ChatGPT quietly reshapes product management behind the scenes.

Here’s my stance: ChatGPT doesn’t replace product judgment. It amplifies it. Used well, it accelerates product discovery, clarifies roadmaps, sharpens positioning, and strengthens stakeholder management. Used poorly, it creates noise and risk. What follows are the specific workflows and prompts that reliably save me hours while protecting quality and trust.

Discovery and research are where I see the biggest upside. I use ChatGPT to draft interview guides, transform raw notes into theme clusters, and generate “Jobs to Be Done” problem statements—then I validate them with customers. I anonymize inputs to protect privacy and follow privacy-by-design and data governance commitments; AI risk management matters more than ever when we’re handling real user data.

When I move from insight to definition, ChatGPT helps me spin up crisp PRDs and user stories. I provide context about our users, constraints, and success metrics and ask for structured outputs: goals, non-goals, acceptance criteria, and risks. This keeps our product trios aligned and focused on outcomes vs output OKRs, not just shipping features.

For competitive analysis and positioning, I feed in public information and ask for points of parity, points of differentiation, and potential messaging angles. I treat the output as a starting point for my value proposition and battlecards—not the final word. It’s a fast way to surface hypotheses and pressure-test our product-led growth narrative.

Roadmapping and sprint planning also benefit. I use ChatGPT to map dependencies, draft milestone narratives, and transform epics into well-formed backlogs. When we align quarterly plans, I ask for risk scenarios and contingency options so we can make trade-offs explicit before we commit.

On analytics and experiments, ChatGPT is my drafting partner. It helps me define A/B testing plans, clarify the minimum detectable effect (MDE), and outline instrumentation requirements. I still verify numbers in our analytics stack, but the scaffolding is done in minutes, not hours—freeing me to focus on retention analysis and activation levers.

Stakeholder communication is where the time savings compound. I use ChatGPT to produce executive summaries, QBRs vs OKRs comparisons, and board-ready narratives that highlight outcomes, risks, and next steps. It’s a powerful way to stay crisp and consistent across leadership updates without losing the nuance that matters.

Prompt patterns make or break results. I keep four rules: set the role, provide rich context, define constraints, and specify the output format. For example: “You are a senior PM advisor. Context: [user, market, problem]. Constraints: [privacy, timeline, budget]. Output: PRD with goals, acceptance criteria, and risks.” With larger inputs, I use context window management by chunking content and asking for summaries before synthesis.

For internal knowledge, I lean on a retrieval-first pipeline. Instead of pasting long docs, I reference curated, approved sources so answers track to current reality. CustomGPT workflows and a simple ChatGPT connector help with governance: they increase speed while reducing the chance of hallucinations and stale information.

Guardrails are non-negotiable. We never paste sensitive data into prompts; we redact PII, spot-check against source-of-truth systems, and red-team important outputs. AI risk management isn’t just a checkbox—it’s how we maintain trust while scaling productivity with gen ai.

Finally, enablement turns personal productivity into team capability. I run short playbooks for empowered product teams: discovery synthesis, PRD drafting, roadmap storytelling, and stakeholder-ready updates. The result is higher-quality thinking, faster cycles, and fewer meetings to align on the essentials.

ChatGPT for product managers isn’t hype; it’s a practical edge when you apply discipline. Start with one workflow that drains your time, add a prompt template, and measure the outcome. In a week, you’ll have proof. In a quarter, you’ll have a new operating system for how your team learns, decides, and ships.

Inspired by this post on Product School.

November 17, 2025
Vibe Check Part 2: Feel Something, Measure Everything with High-Impact Amplitude Analytics

I build products with equal parts intuition and instrumentation. When a campaign’s purpose is to spark a feeling, I still demand proof that those moments translate into measurable outcomes. Learn how you can use Amplitude to better track your vibe marketing initiatives in part 2 of our 3-part series.

Vibe marketing works when emotion and evidence move in lockstep. In my practice, I rely on Amplitude analytics as a unified analytics platform to connect the emotional resonance of a message to product-led growth—tracking how a compelling story influences user activation, retention, and revenue. The goal is simple: feel something, measure everything.

I start by instrumenting the journey around the vibe itself. That means a clean event taxonomy and consistent properties that capture the creative theme, channel, audience segment, and context (for example: campaign_id, creative_theme, entry_channel, audience_mood, landing_variant). Good data governance is non-negotiable—if the data isn’t trustworthy, neither are the insights. With this foundation, I can attribute emotional narratives to downstream behaviors with confidence.

From there, I map the funnel and define activation with intent. I track how vibe-forward touchpoints influence key milestones—first value moments, time-to-activation, and early feature engagement—then ladder those signals into retention analysis. Cohorting users by creative theme or channel helps me see which vibes convert initial curiosity into durable product habits, and which only produce short-lived spikes.

Experimentation is where the rigor shows. I use A/B testing to isolate the impact of a specific narrative, headline, or creative treatment, and I size tests based on minimum detectable effect (MDE) to avoid underpowered decisions. Guardrail metrics (activation, retention, and NPS) protect the experience while I iterate. When the numbers are tight, I supplement with directional reads—session quality, content depth, and return visits—while staying honest about causality.

Operationally, my team lives in shared Amplitude dashboards and notebooks. We annotate launches, align on outcomes vs output OKRs, and review weekly trendlines with our GTM partners. This cadence keeps empowered product teams focused on what matters: which vibes accelerate onboarding, deepen engagement, and ultimately improve unit economics. When a story resonates, the data should echo it across the funnel.

The biggest pitfalls I see are vanity metrics and disconnected systems. To avoid them, I link campaign data to product behavior, unify identifiers across tools, and ensure CRM integration so we can follow the customer journey end-to-end. The payoff is clarity: I can tell a creative team exactly which narrative unlocked user activation and which one stalled—then iterate with speed and precision.

Vibe marketing isn’t soft; it’s strategic. When we respect the craft of emotion and the discipline of measurement, we build experiences that people love and businesses depend on. If you’re ready to upgrade how you track the intangibles, Amplitude gives you the instrumentation to turn feelings into forward motion.

Inspired by this post on Amplitude – Best Practices.

November 13, 2025
The Product Positioning Statement Playbook: Build a Message That Wins and Endures

Your product positioning statement decides if you stand the test of time. I’ve seen this truth play out across launches, pivots, and category-defining moments—when the positioning is razor sharp, everything from roadmap to revenue snaps into alignment. When it’s vague, teams ship features, but customers don’t buy the story.

At HighLevel, I’ve led product trios and go-to-market teams through the hard work of distilling complex value into a single, credible promise. The pattern is consistent: the best positioning clarifies who we serve, the problem we own, the market category we play in, and the competitive differentiation that earns us the right to win.

Positioning is not a tagline or a homepage headline; it’s the narrative spine that informs value proposition, messaging, pricing, user activation, sales enablement, and product-led growth. It’s also how we drive internal focus—shaping outcomes vs output OKRs, roadmap trade-offs, and investment bets with discipline.

Here’s the anatomy I rely on: target customer and context; problem worth solving; category anchor (what buyers already recognize); value proposition (the outcome we deliver); points of parity (table stakes we meet) and points of differentiation (where we win); and proof—evidence that reduces risk for the buyer. When each element is explicit, your product positioning becomes both compelling and testable.

Use a simple scaffold to draft quickly: For [target customer], who [urgent need or job-to-be-done], [product] is a [recognized category] that [core value proposition]. Unlike [primary alternatives], it [distinct, defensible differentiation]—proven by [evidence: results, usage, social proof, or integrations]. Write it plainly enough that a sales rep can say it and a customer can repeat it.

Then pressure-test. In product discovery, validate the language with real customers—do they self-identify as the target and echo the outcome? In analytics, check if activation and retention analysis improve when onboarding, in-app guides, and product tours mirror the positioning. In go-to-market strategy, A/B test messaging in campaigns and sales conversations, and listen for shorter time-to-understanding and cleaner objection handling.

Expert products operationalize positioning across the journey. The category and value proposition show up consistently on the pricing page, inside onboarding tooltips, in CRM integration notes, and within sales collateral. Product management leadership, marketing, and sales align weekly on one narrative, and product-led growth metrics verify that narrative with behavior, not just opinions.

To write one that sticks, I take this sequence: define the narrowest viable target; articulate the must-solve problem in the customer’s words; choose a category buyers already understand; frame a value proposition that promises an outcome, not a feature; document points of parity so you don’t over-claim; highlight two to three competitive differentiation pillars; add proof; and cut jargon until a smart outsider gets it in one read.

Common failure modes include trying to be for everyone, leaning on feature soup instead of outcomes, skipping proof, and drifting from what the product can actually deliver. The fix is focus: fewer claims, clearer benefits, and evidence that eliminates buyer uncertainty.

If you need a fast start, run a 30-minute working session: five minutes to align on the target and problem, five to choose the category, ten to draft value proposition plus parity and differentiation, five to add proof, and five to define two experiments (one discovery conversation, one A/B test) that validate the language this week. Learn how other expert products do it and how to write one that sticks—then let data and customer language refine every word.

Great positioning earns clarity, confidence, and compounding advantage. When we get it right, the market tells us quickly—prospects move faster, users activate with less friction, and the team finally feels like it’s rowing in the same direction.

Inspired by this post on Product School.

November 13, 2025