Context is king in AI-powered product work—and I felt that deeply while digging into “Context is King – All Things Product Podcast with Teresa Torres & Petra Wille.” The conversation affirmed a truth I see daily: AI becomes a powerful teammate only when we give it the right context, just as we do with empowered product teams. When we treat AI like a colleague joining mid-flight—without our company history, industry nuances, or strategy—we instantly unlock better outcomes.
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Here’s what stood out and how I’m applying it. First, most AI outputs fail without proper context. That’s not a model problem; it’s a leadership problem. Thinking of AI like onboarding a new intern is the right mental model—start with the minimum viable context, then iterate. Practical first steps matter: decision logs, clear success metrics, and structured documentation. The art is balancing enough context to guide performance without overloading the system. The parallels are striking: the way we create strategic context for product trios and teams is the same way we’ll empower agentic AI systems.
In my teams, we prepare for AI collaboration by operationalizing context. We keep decision logs to capture the why behind choices, use outcome-based success metrics (not just output), and maintain machine-readable documentation that LLMs for product managers can parse reliably. We define guardrails up front—constraints, customer segments, privacy-by-design considerations, and the non-goals that often trip up gen ai. This foundation turns AI from a novelty into a force multiplier for product discovery and product roadmapping and sprint planning.
I use a simple “context pack” to onboard AI agents and teammates alike: 1) business goals and outcomes, 2) constraints and guardrails, 3) canonical artifacts (like PRDs, journey maps, interview notes), 4) domain vocabulary and definitions, and 5) operating procedures (how we make decisions, when to escalate, what good looks like). Start small, then refine as the AI demonstrates capability. This mirrors great onboarding—and it works just as well for agentic AI as it does for humans.
Not all context is helpful. More isn’t better; the minimum effective context is. I resist the urge to dump our entire Confluence on an AI system. Instead, I progressively reveal relevant details—just like I would with a new PM on a complex problem space. This keeps signals high, noise low, and performance measurable against clear success metrics.
If your org isn’t adopting AI yet, don’t wait. You can become AI-ready now by documenting strategic intent, decision rationale, and definitions in structured, searchable, machine-readable ways. Treat this as core AI Strategy work that strengthens empowered product teams—regardless of tooling—while building your AI product toolbox for tomorrow.
For those who want to explore further, these resources and mentions are a strong complement to the episode’s themes.
Follow Teresa Torres: https://ProductTalk.org
Follow Petra Wille: https://Petra-Wille.com
Agentic AI
Teresa’s new podcast, Just Now Possible in Youtube, Apple Podcast, and Spotify
Petra’s Coaching Packages
ChatGPT
Henrik Kniberg’s talk at Product at Heart on treating AI agents like interns
Teresa’s webinars on how she built the Product Talk Interview Coach: Behind the Scenes: Building the Product Talk Interview Coach and How I Designed & Implemented Evals for Product Talk’s Interview Coach
Josh Seiden’s blog series about AI
Teresa’s new blog posts: 15 Ways to Use AI at Home (and Fill Your AI Product Toolbox) and 21 Ways to Use AI at Work (And Build Your AI Product Toolbox)
Petra's new blog post: Why Context, Not Just Data, Will Define AI-Ready Product Teams
Have thoughts on this episode or how you’re preparing your teams to collaborate with AI? Leave a comment below—let’s compare playbooks and level up together.
Digital transformation rewired our systems; AI transformation rewires how we learn, decide, and compete. “AI transformation goes beyond automation to create adaptive, intelligent organizations. Discover why it’s the next imperative and how to measure success.” That statement captures what I experience daily: we’re moving from scripted workflows to living systems that improve with every interaction.
When I talk about AI transformation, I’m not describing a tool rollout. I’m describing an operating model where data, models, and product strategy converge to create compounding advantage. In practice, that means agentic AI orchestrating tasks, robust data governance and privacy-by-design from day one, and empowered product teams that ship, measure, and iterate at high tempo.
The imperative is strategic, not merely technical. Markets are compressing cycle times, and customers now expect intelligent experiences by default. Organizations that master AI Strategy and product-led growth will set the pace—using AI for competitive differentiation rather than feature parity.
This shift changes how I build teams and backlogs. I lean on product trios, forward deployed engineers, and tight product discovery loops to reduce uncertainty early. We design for resilience and learning: human-in-the-loop feedback, clear escalation paths, and telemetry that turns every interaction into a hypothesis test.
Governance is a first-class feature. AI risk management, data governance, and threat detection and response sit alongside performance metrics in the same dashboard. We codify guardrails—policy, provenance, and permissions—so innovation scales safely and sustainably.
Measurement is where transformation becomes real. I anchor on outcomes vs output OKRs tied to customer value and revenue impact. At the product layer, I track activation, time-to-value, retention, and adoption by persona. For ML quality, I monitor precision/recall, coverage, hallucination rate, and model drift. In experimentation, A/B testing with a thoughtful minimum detectable effect (MDE) prevents false wins, while Amplitude analytics, Pendo, and Intercom instrumentation expose where guidance or UX writing can unlock activation.
The fastest wins often start in service and sales. A customer support ai strategy can deflect tickets with high-resolution answers while escalating edge cases to humans with full context. CRM integration with HubSpot and a ChatGPT connector enables reps to generate next-best-actions, summarize calls, and personalize outreach—measurably lifting conversion and lowering cost-to-serve.
On the build side, LLMs for product managers and gen ai for product prototyping accelerate discovery cycles. I use CustomGPT workflows to validate value propositions quickly, then harden successful flows with engineering. Throughout, product positioning and a crisp value proposition ensure that what we ship is understandable, differentiated, and priced to match ROI—consumption SaaS pricing when usage scales value.
If you’re getting started, begin with a single, high-frequency journey, instrument it deeply, and publish transparent OKRs. Pair empowered product teams with clear governance, and iterate toward agentic AI experiences. The payoff isn’t a one-time launch; it’s a continuously learning system—and a culture—that compounds advantage release after release.
I recently shared 15 ways I'm using AI at home—from fixing cooking disasters to researching school bonds—and those experiments turned into real skills: learning to chat with large language models (LLMs), providing the right context, verifying results, and more.
Now it’s time to apply those same skills at work. The stakes feel higher, the problems are more complex, and we have to navigate when and how AI is acceptable at work. But the foundation we built at home makes the leap far less intimidating.
My goal is to inspire you to start experimenting (if you aren’t already). Along the way, you’ll add practical techniques to your AI product toolbox.
A clean address form ready for automation: fields for Attention, Address, City, State, ZIP, and Country invite AI-driven autofill, validation, and routing, accelerating workflows and reducing manual typing at work.
Using AI at home taught the basics—prompting, context windows, and hallucinations. At work, I layer in orchestration and automation. Don’t worry; we’ll take it step by step.
To make this actionable, I organize my work use cases by complexity, so you can start at the top and move down as your confidence grows. I group them into five buckets: Translator, Do the Work, Researcher, Writing Partner, and Coding Partner. Everyone can access the first three categories; I reserve the last two for subscribers.
Clear course policies at a glance: switch cohorts up to 14 days before start, transfer a seat to another student until the day prior, and get scaled group discounts for Deep Dive courses, though Fundamentals is excluded.
Translator: I’ll start simple with low-stakes examples that build confidence and momentum.
1) Translate this email for me. My last name is common in both Spanish and Portuguese, so people often assume I speak both. I can get by in Spanish, but not Portuguese. When I get an email in another language, I ask ChatGPT for a translation. I used to use Google Translate, but ChatGPT tends to interpret context better. It’s a quick win that gets you comfortable with LLM interactions.
Curious which formats perform best? These heatmaps compare category averages for impressions, engagements, and new followers—spotlighting podcasts for reach and 'Other' for follower gains.
2) Parse this address for me. I live in the United States and work with companies around the world. In Xero, I have to enter addresses by street, city, state/region, country, and zip code. For international addresses, I’m not always sure how to parse fields. ChatGPT is great at this, so I created a CustomGPT to avoid rewriting the prompt. I paste the address, and it returns values mapped to Xero’s fields. If you’re new to CustomGPTs, think of them as reusable prompt-and-context bundles you can share with colleagues. Skills I built: when to use a CustomGPT versus an ad hoc prompt, and how to templatize repetitive formatting tasks.
Do the Work: This is where the magic shows up—AI accelerates execution—provided you set clear guardrails and keep humans in the loop where quality matters.
This concise social post tackles the “no differentiation” myth in B2B, highlighting how segmentation, team alignment, and a clear view of competitors reveal real product value—prompting readers to reflect and join the discussion.
3) Customer service assistant. My company offers a range of products and services, so we created a knowledge base with common questions and template answers to train support. But finding the right response in the moment is slow. I uploaded our content into a CustomGPT and instructed it to surface the most relevant templates, given an inbound email. The key decision: I did not let the model draft final replies. My admin uses suggestions to respond faster, but she remains responsible for the email content. Skills I built: discerning where human oversight is essential and using LLMs to speed up, not outsource, attention-intensive work.
4) Social media analysis. I share my work on social channels and want to know what resonates. LinkedIn lets me export analytics on top posts. Each month I export the last 30 days, ask a CustomGPT to create topic and category heat maps for impressions, engagements, and followers, and I chart trends over time. Patterns become obvious—personal stories drive impressions and engagement; short-form video drives followers. This workflow, inspired by Andy Crestodina at Orbit Media, turns raw analytics into actionable content strategy. Skills I built: using LLMs for data analysis and visualization, moving from exports to insights, and spotting outliers at a glance.
An AI-powered contract review snapshot flags risky clauses and where to push back. Clear labels—Dealbreaker, Needs Redlining, None Found—help teams tighten IP rights, social media controls, refund terms, and injunctive relief.
5) Article summaries. I used to share Worthy Reads—recommended articles—on LinkedIn and X, and I wanted stronger summaries. I asked Claude to generate them in the author’s voice, not “LLM voice.” I gave tone and style guidelines, writing samples, and a clear structure. Quality improved with each iteration. To save time, I automated the workflow with a Zapier zap: when I add a new article to my database, the Anthropic API generates a draft summary and emails it to me for a quick human review. If it looks good, I do nothing. If not, edits are one click away. Skills I built: providing precise context for tone and structure, creating a simple automation, and keeping a light human-in-the-loop review for quality.
6) ContractBot. I regularly review long legal documents and dislike every minute of it, so I built ContractBot as a CustomGPT. It started with a one-sided contract full of red flags—intellectual property, morality clauses, payment terms, and more. I asked ChatGPT to identify issues, we worked through them, and then I had ChatGPT write the reusable prompt that became ContractBot. Now I upload any new contract and get a summary of redlines tailored to my preferences. When new issues arise, I update the CustomGPT prompt, and it evolves with me. Skills I built: iterating preferences over time, using LLMs to translate and revise dense documents, and leveling information asymmetry during negotiations.
Need customer interview guidance fast? This snapshot rounds up five high-ranking guides with quick notes—perfect for scanning options and choosing the best how-to. Use it to kickstart research and structure your interview plan.
7) SEO keyword analyzer. “SEO is dead. People don’t use search engines. Now they just ask LLMs.” But LLMs still use search engines—so SEO is not dead. I still care about ranking for relevant terms, and I use ChatGPT to help. I give it a target keyword and one of my articles, then ask it to analyze the top ten Google results and highlight what they do that I don’t. I get a prioritized gap analysis. I don’t take every suggestion—I write for humans first—but many SEO improvements also boost readability, so it’s a win-win. This workflow, also inspired by Andy Crestodina, made me care about SEO because the effort is now minimal. Skills I built: competitive research and gap analysis, balancing SEO with human readability, and codifying a repeatable research pattern.
8) Landing page analyzer. I don’t love writing sales copy, but landing pages matter. I use ChatGPT to critique my course landing pages, with rich context: an ideal customer profile from real discovery interviews, a course syllabus, student testimonials, and the same knowledge base my support team uses. With all that context, I ask for a critique from the buyer’s point of view. Context is king—the more I provide, the sharper the feedback. I don’t accept every suggestion, and I still run demand and usability tests, but a second set of (virtual) eyes helps me move faster on a task I’d otherwise procrastinate. Skills I built: using LLMs to push through resistance, feeding the right context, and soliciting targeted “expert” feedback.
Messaging teardown in a sleek, dark theme shows how to turn interview findings into sharper copy: center ICP struggles with adoption and scaling, and rework the hero to speak directly to product leaders under pressure.
9) Podcast participation guide. I launched a new podcast, Just Now Possible, where I interview product teams about the AI products and features they’re building. Guests often need company approval to join, and I’d never had to ask for permission before. I set up a ChatGPT Project with background files—target listener, goals, and differentiation strategy—then asked it to draft a one-pager for executives explaining why their team should participate. It nailed the brief because the Project was already loaded with the right context. Skills I built: setting up Projects for ongoing domains and compounding context over time for higher-quality assistance.
10) Podcast episode titles, descriptions, show notes, and chapter marks. In the same Project, I paste episode transcripts and ask for titles, descriptions, show notes, and chapters. As volume grows, I’m transitioning this into a CustomGPT with actions so I can click “Generate episode metadata,” paste the transcript, and go. Later, I’ll add actions for social posts and more. I don’t need to design the full system upfront; I evolve it as needs emerge. Skills I built: when to move from Projects to CustomGPTs, how to define actions, and how to evolve LLM tools incrementally.
Explore how the Just Now Possible podcast turns real AI product work into practical guidance. This overview invites PMs, designers, and engineers to share decisions, showcase features, strengthen employer brand, and gain recruiting assets.
Researcher: If you’ve tried using LLMs as an expert researcher at home, the returns at work are even better. Here are two recent examples.
11) Choosing a new blogging/newsletter platform. After 14 years on WordPress, my site started breaking—plugin auto-updates caused critical errors, Google flagged 500s and performance issues, and I was over managing plugins. I’d also switched from Mailchimp to Kit and wasn’t thrilled. I considered Substack but had mixed feelings. I laid out constraints and goals in ChatGPT, compared options, and landed on Ghost. Before committing, I used ChatGPT to dive deep: theme customization, memberships, API documentation, and migration tasks. On a free trial, ChatGPT walked me through exporting from WordPress and importing into Ghost; Claude Code helped with theme tweaks. By the end of two weeks, I had imported data, customized the site, validated fit, and built confidence. We officially migrated in August 2025. Skills I built: tackling big projects with an AI guide on call, running structured vendor comparisons, and piloting major tech decisions with AI-assisted validation.
A draft episode description in dark mode outlines a talk on creating an AI Teacher Assistant for K–5 schools—covering post‑COVID pressures, why a chatbot interface failed, building a first RAG system, and lessons from real teacher use.
12) Academic research. I draw heavily from research on decision-making, problem-solving, and learning science, but I’m not an academic and can’t spend hours in journals. ChatGPT’s Deep Research changed that. Quarterly, I generate a report on topics like decision-making with parameters such as date ranges, peer-reviewed sources, and clear citations. I automated the pipeline so reports land in my Readwise inbox alongside other articles. I also seeded a course design Project in ChatGPT with Deep Research reports on scaffolding, modeling, and learning styles, so my course design support is evidence-based by default. Skills I built: running Deep Research on-demand and automating it so staying current is effortless.
Learning to use AI as a thought partner has been the biggest unlock for me. It’s hard to describe, so I’ll show you with detailed examples. I’ll start with how I write with AI—headline generation and copy editing—and quickly get to more advanced workflows. You’ll see how I set up subagents to review my writing from different perspectives, where I let LLMs draft versus where I insist on drafting myself, and why I now write in VS Code with Claude Code following along.
See how Ghost uses Handlebars to render posts and customize themes quickly. The screenshot highlights template helpers and a straightforward flow: download a theme, edit locally, upload in Ghost Admin, then activate.
These workflows helped me produce more, higher-quality content, and—unexpectedly—brought the joy back to writing.
I’ll also share how I use LLMs to help me code: how ChatGPT taught me to set up and use a Python Jupyter Notebook for eval data analysis, how I pair program with Claude Code, how I get Claude Code to generate high-quality unit and integration tests, and how I leveled up error handling with both Claude Code and ChatGPT. I have a light coding background; I couldn’t have done this without LLMs. Even if you don’t code today, there’s a lot here you can apply.
Evidence-backed scaffolding methods at a glance—gradual release, cognitive apprenticeship, task simplification, mentoring, and communities of practice—show how to teach AI skills, build confidence, and accelerate adoption at work.
As a reminder, those last two sections—my Writing Partner and Coding Partner playbooks—are for paid subscribers. I’ll also use comments to dig into your workflows. I hope you’ll join us.
I was initially reluctant to use LLMs as a writing partner. I’m not trying to outsource my thinking; writing is how I think. But staring at a blank page is real. I write, delete, and write again. The breakthrough was realizing the model doesn’t have to think for me—it can help me think more clearly. It can tell me when a draft is weak, offer structured feedback, and help me brainstorm ways to get unstuck. That’s how I began using LLMs as a true thought partner.
Go hard early is more than a mantra—it’s a product strategy. When I study the most durable enterprise companies, I see the same pattern: you win by shipping fast, obsessing over the customer’s day-to-day pains, and delivering consumer-quality experiences to business buyers. That lens is exactly why Serval’s recent momentum caught my attention and why the lessons behind it matter for every product and IT leader building in AI.
Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical.
From my vantage point, the most counterintuitive lesson here is the power of building “in existing categories.” Rather than inventing a new market, the better move can be to redefine expectations inside a known one—where buyers, budgets, and success criteria already exist. That’s how you compress sales cycles, build trust rapidly, and create a wedge for product-led growth without boiling the ocean.
Another playbook thread I admire: turning “hard mode” into a moat. The teams that lean into gnarly integrations, real workflow depth, and enterprise-grade reliability end up compounding an advantage that’s very hard for fast followers to copy. That mindset shows up in Serval’s platform strategy and, more importantly, in how they translate complex IT work into something that feels intuitive on day one and powerful on day 100.
Customer intimacy sits at the center of that strategy. The customer interview question that unlocked the IT buyer’s hidden pain points is the kind of move I try to operationalize across product trios and forward-deployed teams. When you ask not just, “What do you do?” but, “What do you do when everything breaks?” you surface the real constraints: shadow runbooks, brittle scripts, brittle processes, and the political friction that slows down response times. That’s where durable value—and competitive differentiation—lives.
How Serval’s automation builder uses AI to generate code-based workflows is a particularly smart architectural choice. Code-first doesn’t mean hard-to-use; it means source-controlled, interoperable, and shareable across teams—exactly what IT leaders want when automation moves from side project to system of record. Tie that to agentic orchestration and you get reliable automations with clear observability, safety rails, and the ability to scale without collapsing under edge cases.
I’m also a believer in redefining engineering and PM roles with forward-deployed engineers. When engineers partner directly with customers, discovery accelerates, prioritization sharpens, and product bet quality improves. You avoid ping-ponging requirements through layers, and you raise the hiring bar for true product creators who can think in outcomes, not just output.
Keeping the hiring bar high in an AI-native startup isn’t optional—it’s existential. The best teams screen for candidates who can reason from first principles, ship quickly with taste, and articulate the value proposition in plain language. The ultimate hiring litmus test is whether someone can improve the product on day one by clarifying a user journey, simplifying a workflow, or tightening a metric that actually matters.
There’s also Why there’s a “land grab” moment right now in enterprise AI. Incumbents are strong on breadth but often slow to re-architect for AI-native workflows. New entrants that show up with opinionated defaults, pragmatic security, and crisp buyer narratives can establish points of parity quickly while extending into true points of differentiation. That’s the window to seize—especially when building for mid-market and enterprise.
Here are the core themes I took away and how I translate them into practice across product roadmapping and sprint planning, product discovery, and go-to-market strategy.
Why building “in existing categories” can be more powerful than creating new ones. Use the market’s mental models, measure against known alternatives, and win by delivering a meaningfully better experience—not by forcing buyers to invent new procurement paths.
The lessons from Verkada that shaped Serval’s platform strategy. Treat UX polish as a strategic asset, make setup effortless, and let power users go deep without friction. Consumer-grade quality is not a veneer; it’s a trust accelerator in enterprise.
The customer interview question that unlocked the IT buyer’s hidden pain points. Go beyond happy-path discovery. Ask about the 3 a.m. moments, the panic buttons, and the messy handoffs—then design for those first.
How Serval’s automation builder uses AI to generate code-based workflows. Pair AI generation with reviewability, versioning, and safe rollbacks. Make it easy to see, test, and share what the agent is doing under the hood.
Redefining engineering and PM roles with forward-deployed engineers. Collapse feedback loops by putting builders where the problems are. It’s the fastest path to product-market fit lessons and real-world reliability.
Keeping the hiring bar high in an AI-native startup. Look for taste, speed, and ownership. Optimize for people who can both prototype with gen ai and ship production-hardened systems.
Why there’s a “land grab” moment right now in enterprise AI. Move quickly, but anchor on outcomes. Land with a wedge use case, expand with measurable value, and maintain clear points of parity while you deepen differentiation.
If you want to follow or explore the companies and leaders referenced, these links are a useful starting point.
This podcast on all platforms: https://review.firstround.com/podcast
References:
Alex McLeod: https://www.linkedin.com/in/alexmcleodio/
Clay: https://www.clay.com
Cloudflare: https://www.cloudflare.com
Cursor: https://cursor.sh
Filip Kaliszan: https://www.linkedin.com/in/kaliszan/
Hans Robertson: https://www.linkedin.com/in/hansrobertson
Linear: https://linear.app
Okta: https://www.okta.com
Rippling: https://www.rippling.com
Serval: https://www.serval.com/
ServiceNow: https://www.servicenow.com
Verkada: https://www.verkada.com
Workday: https://www.workday.com
Timestamps and topic highlights for easy navigation and deeper study:
(02:25) Lessons from holding different product roles
(07:29) Turning “hard mode” into a moat
(10:49) The early days of Serval
(12:59) Scratching the founder itch
(14:57) Unconventional interview techniques
(17:47) Solving core interview challenges
(21:10) Planning the early product roadmap
(23:03) The surprising power of patience
(26:12) Serval’s impressive technical advantage
(27:35) Disrupting legacy incumbents
(31:13) Building for mid-market and enterprise
(33:35) Serval’s enduring roadmap
(36:08) How to sell to an existing market
(39:16) The evolving role software plays
(43:55) Building for AI that didn’t exist yet
(49:49) Serval’s forward-deployed engineers
(58:31) The hybrid PM-GM
(1:00:27) “You can over-prioritize”
(1:02:48) The unexpected value of panic buttons
(1:04:50) What Serval looks for in new talent
(1:07:01) The ultimate hiring litmus test
(1:13:59) Building out Serval’s go-to-market function
(1:16:31) The evolving IT market in 2025
My bottom line: build where budgets already live, ship with uncompromising UX, embed engineers with customers, and hold the line on talent. Do that, and you won’t just keep up with the enterprise AI “land grab”—you’ll define the standard others have to meet.
Building AI agents looks deceptively simple right now. After leading multiple agentic AI initiatives, I’ve learned that the difference between a demo and a dependable product comes down to disciplined product discovery, ruthless scoping, and a clear AI Strategy that aligns with business outcomes. Here are four common misconceptions I correct early with stakeholders—and the practices I use to avoid expensive detours.
Misconception 1: “An LLM plus a few prompts is a production-ready agent.” In reality, production-grade agents require orchestration and rigor: tool-use and retrieval, memory design, state management, deterministic fallbacks, and continuous evaluation. I instrument Agent Analytics from day one to trace tool calls, latency, error codes, and cost per task; then I use A/B testing with a clear minimum detectable effect (MDE) to validate improvements before broad rollout. This is where product roadmapping and sprint planning matter—sequencing capabilities so we avoid building speculative features that don’t move outcomes.
Misconception 2: “More autonomy is always better.” The right autonomy level is contextual and risk-adjusted. For high-stakes workflows, I design for human-in-the-loop and role-based guardrails, grounded in privacy-by-design and data governance. Policies like least-privilege access, audit logs, and reversible actions reduce operational risk while still delivering leverage. In practice, this hybrid approach also controls cost: narrower scopes, clearer prompts, and bounded tool access reduce hallucination surface area and improve reliability—key to AI risk management.
Misconception 3: “If we build it, users will adopt it.” Adoption is earned with thoughtful onboarding and in-app guidance, not promised by a feature launch. I pair agent launches with targeted product tours, contextual tooltips, and progressive disclosure to drive user activation and product-led growth. 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. Whether you use Pendo or a comparable solution, the principle stands: instrument the experience, run experiments, and iterate quickly based on evidence, not intuition.
Misconception 4: “Security, compliance, and governance can wait.” Deferring controls is a false economy. I embed AI risk management from day zero: prompt injection defenses, PII redaction, DLP, grounding and citation strategies, and threat detection and response. Clear data retention policies, vendor diligence, and model evaluation standards keep leadership, security, and legal aligned. This is the crux of building trust—and it’s far easier to design up front than to retrofit under pressure.
How I execute in practice: start with a tightly framed use case tied to a measurable outcome; define outcomes vs output OKRs; build a slim vertical slice to validate feasibility; instrument Agent Analytics from the first commit; ship behind feature flags; and operationalize learning loops across support, success, and GTM. The result is a durable path to product-market fit for agentic AI—one that compounds learning while minimizing blast radius.
The leaders who win with AI agents won’t be the ones who move fastest in a demo. They’ll be the ones who manage risk transparently, learn in public with their users, and turn continuous insight into competitive differentiation. If you’re planning your next agent milestone, align the roadmap to outcomes, treat governance as a feature, and make adoption your North Star.
I spend a lot of time reviewing how customers move through our product and where their momentum stalls or accelerates. The tools you use to build and optimize software experiences are evolving. That simple truth reshapes our strategy every quarter, from the analytics we trust to the in-app touchpoints we design and the experiments we run to improve product-led growth.
When I say SXM, I’m talking about a comprehensive software experience management approach that unifies analytics, experimentation, in-app guides, messaging, and feedback loops. SXM vs. the rest is the real-world choice between an integrated platform and a patchwork of point solutions. I’m not married to one path; I’m obsessed with outcomes—speed to learning, lower friction for teams, and compounding retention gains.
The foundation is a unified analytics platform and a clean, consistent event schema. From there, I pair behavior analytics with in-app orchestration: tools like Amplitude analytics for deep behavioral insights and Pendo for targeted in-app guides, product tours, and contextual nudges. I instrument rigorous A/B testing with a clearly defined minimum detectable effect (MDE) and follow through with retention analysis to validate whether an uplift sticks beyond vanity metrics. Great UX writing and thoughtful tooltip design often make the difference between a nudge that converts and a prompt that gets ignored.
I choose between best-of-breed and platform consolidation using first principles decision making. If a point solution unlocks a capability that meaningfully advances our product discovery or activation work, I adopt it. If multiple tools converge on the same points of parity, I consolidate to streamline governance, reduce integration overhead, and accelerate delivery. The goal is not more software; it’s faster, clearer learning that informs product positioning and drives customer value.
AI now sits at the center of this stack. I apply gen ai and agentic AI to accelerate hypothesis generation, automate cohort detection, draft UX microcopy, and suggest next-best actions inside the product. That said, AI risk management, privacy-by-design, and data governance are non-negotiable. I won’t trade trust for tempo; we can have both by putting guardrails around training data, access controls, and evaluation criteria.
Operating rhythm matters as much as tooling. Product trios set outcomes vs output OKRs, then test and iterate—starting with onboarding, activation, and the moments that trigger value realization. We build in measurable in-app guides, run A/B testing with tight feedback cycles, and keep our go-to-market strategy aligned so every nudge, message, and feature release supports product-led growth.
My playbook is simple: clarify the outcomes, instrument the journey end-to-end, choose the smallest toolset that can answer the biggest questions, and learn faster than the market. Map critical paths, standardize taxonomy, and make experimentation a habit—not a project. Then double down where signal is strongest and retire anything that adds minimal lift to retention or expansion.
SXM isn’t a buzzword; it’s a disciplined way to build software that feels intuitive, responsive, and valuable from the first click. With the right blend of analytics, in-app guidance, experimentation, and AI—grounded in strong product management leadership—we can turn insights into momentum and momentum into durable growth.
AI has fundamentally changed how I lead design and testing, not by replacing craft, but by compounding it. When my teams pair generative models with time‑tested product management practices, we move faster, learn sooner, and ship with more confidence—without compromising privacy-by-design or quality. The result is a tighter loop from product discovery to product-market fit lessons.
Learn how Pendo’s product design team is using genAI and traditional tools to speed up design and development.
That single line captures my own operating model: blend genAI with established toolchains to accelerate, not shortcut. In practice, I treat AI as a force multiplier for product trios—PM, design, and engineering—so empowered product teams can explore broader solution spaces while staying anchored to outcomes vs output OKRs.
In discovery, genAI helps me synthesize qualitative inputs at scale—interviews, support threads, and in-app behaviors—into testable opportunity statements. I triangulate those insights with a unified analytics platform and Amplitude analytics to spot friction, then use in-app guides and product tours to target learning, recruit the right cohorts, and validate problems before we overbuild.
For prototyping, gen ai for product prototyping is a game-changer. I generate multiple UX writing variants, microcopy, and flows in minutes, then narrow the set using heuristics and stakeholder feedback. Before any A/B testing, we precompute the minimum detectable effect (MDE) and sample size, making sure our experiments are powered to detect meaningful differences, not noise.
In testing, I combine classic A/B testing with AI-assisted analysis to surface patterns faster. GenAI drafts experiment summaries, flags anomalous segments, and proposes follow-up tests, while my team makes the final calls. We deploy targeted in-app guides to onboard users into trials, monitor adoption via event telemetry, and iterate quickly until the value proposition is unmistakable.
Execution depends on rigor and guardrails. We codify AI risk management and data governance policies, keep humans-in-the-loop for critical judgments, and log model prompts and outputs for auditability. This lets us move with speed and integrity, aligning stakeholder management, product roadmapping and sprint planning, and go-to-market strategy around measurable outcomes.
The payoff is material: shorter cycle times, clearer value narratives, and stronger product-led growth curves. By fusing genAI with traditional practices, we preserve the craft of design while scaling our capacity to learn. That’s how we differentiate—through faster insight generation, smarter testing, and experiences that feel unmistakably intuitive.
I’m gearing up for INDUSTRY 2025: The Product Conference in Cleveland, Ohio, and I can already feel the energy that comes when the brightest product minds gather. As someone who lives at the intersection of product management leadership, execution discipline, and customer-centric innovation, this event is where I refine my craft and pressure-test my roadmap against the best.
Join Pendo at INDUSTRY in Cleveland, Ohio.
Reason 1: Elevate strategy from outputs to outcomes. I’m looking forward to sharpening how we align outcomes vs output OKRs with product roadmapping and sprint planning. INDUSTRY consistently surfaces practical frameworks to translate vision into measurable value—exactly what empowered product teams need to prioritize with confidence and communicate trade-offs to stakeholders.
Reason 2: Deepen discovery with data that actually drives decisions. I plan to compare notes on product discovery techniques that blend qual and quant—pairing interviews with a unified analytics platform, retention analysis, and a clear minimum detectable effect (MDE) to validate signal. The bar keeps rising on evidence-based decisions, and I’m eager to bring back new ways to reduce bias while accelerating learning.
Reason 3: Double down on product-led growth. From onboarding to activation, I’m focused on refining in-app guides and product tours that meet users at the moment of need. INDUSTRY is a great place to trade patterns for scalable, context-aware experiences that convert, retain, and expand without adding friction—fueling a durable product-led growth motion.
Reason 4: Build a responsible, practical AI Strategy. The conversations around gen ai for product prototyping, agentic AI, data governance, and privacy-by-design are evolving fast. I’m excited to learn how teams are balancing speed with AI risk management—turning experimentation into real features while protecting customers and preserving trust.
Reason 5: Level up leadership and influence. Product management leadership is as much about people as it is about prioritization. I’m excited to trade tactics on stakeholder management, strengthening product trios, and growing ICs through the IC to manager transition. These are the muscles that turn strategy into momentum.
Between keynotes, hallway conversations, and hands-on sessions, I plan to leave Cleveland with fresh approaches to discovery, clearer OKR alignment, and new ideas to operationalize PLG at scale. If you’re passionate about building products that customers love—and businesses rely on—let’s connect and compare notes on what’s working now.
I’ll share my takeaways after the conference, including actionable frameworks, templates, and experiments to run with your teams the very next sprint. If you see me in a session on analytics, onboarding, or AI, say hello—I’m always up for a quick debrief and a few what-would-it-take questions.
Implementing Agentforce isn’t a feature rollout—it’s a strategic shift. In my role building AI-driven products, I treat Agentforce as its own product with clear outcomes, rigorous governance, and disciplined iteration. The objective is to create durable operational leverage inside Salesforce without compromising trust, data integrity, or customer experience.
Learn the ways in which Pendo helps companies design and iterate on their agentic strategy for Salesforce.
I start with product discovery. That means selecting the right use cases, defining the target user, and aligning on measurable outcomes rather than outputs. In practice, I prioritize use cases across sales, service, and marketing using an impact–effort–risk lens, then set crisp success metrics—response time, deflection rate, case resolution, win rate lift, and user adoption. This keeps everyone focused on value creation, not just model novelty.
Next, I design the agentic system with guardrails. I specify agent roles, tools, and policies; define when to escalate to humans; and embed privacy-by-design and data governance from day one. I also build an evaluation harness with offline tests and live A/B testing, ensuring we have a minimum detectable effect that’s meaningful for the business. The goal is to measure outcomes reliably and course-correct quickly.
When building the first slice, I scope narrow and ship fast. For example, start with a constrained service workflow—classify the case, propose a response, and take a safe action—with clear affordances in Salesforce so users understand what the agent did and why. I instrument the experience end-to-end and use Pendo for in-app guides, surveys, and behavioral analytics to reduce onboarding friction and capture real-time feedback at scale.
Iteration is where value compounds. I run weekly reviews of conversations, error taxonomies, and edge cases; adjust prompts and tool access; and maintain a steady experiment cadence. We track outcomes vs output to avoid vanity metrics, and we document learnings to de-risk the next use case. This steady drumbeat builds credibility with stakeholders and confidence with frontline users.
Change management is non-negotiable. I align leaders early, set expectations on what the agent can and cannot do, and define SLAs for humans-in-the-loop. I use product tours to teach new behavior, highlight quick wins, and establish transparent feedback channels. This combination of enablement and accountability accelerates adoption and creates a culture that embraces agentic AI responsibly.
Finally, I scale thoughtfully. Once the first use case demonstrates value, I standardize patterns, unify analytics, and evolve governance as usage grows. I review risk regularly, align OKRs with the roadmap, and keep a tight feedback loop between product, ops, and go-to-market teams. Treating Agentforce as an evolving product—not a one-off project—maximizes impact while protecting the customer experience.
Traditional website chatbots promised instant answers but rarely delivered the depth, context, and actionability modern buyers expect. After seeing patterns of high drop-off and shallow engagement, I stepped back and reframed the problem: We did not need another scripted bot—we needed an AI Agent capable of understanding intent, personalizing responses, and taking meaningful actions in the flow of discovery.
That is why Pendo replaced the website chatbot with an AI Agent. From a product management lens, the decision hinged on three criteria: accelerate time-to-value for visitors, reduce operational overhead through automation, and improve the quality of demand captured at the top of the funnel. An agentic AI approach met all three.
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.
This statement crystallizes the business case. An AI Agent can translate product intent into measurable outcomes by connecting to knowledge sources, analytics, and workflows. Instead of handing off a prospect to a form or a static knowledge article, the agent can surface relevant guidance, qualify interest, book meetings, and even trigger product tours—closing the loop between marketing, product, and customer success.
We anchored the implementation in data governance and privacy-by-design. That meant carefully curating training corpora, instituting role-based access controls, applying guardrails for sensitive topics, and designing graceful human-in-the-loop fallbacks. The result was not just a smarter front door, but a safer one—critical for regulated buyers and enterprise stakeholders.
To validate impact, we ran disciplined A/B testing with a clearly defined minimum detectable effect across conversion, engagement depth, and time-to-response. We also monitored secondary signals such as escalation rate to human support, session quality, and downstream product adoption. Early signals showed more qualified conversations, fewer dead ends, and faster paths to value—exactly the outcomes a product-led growth motion requires.
The experience uplift did not stop at the website. By aligning the agent with in-app guides and product tours, we created continuity from pre-signup exploration to onboarding and activation. Visitors received consistent, contextual help before and after they became users, which strengthened our product positioning and reduced friction across the journey.
Operationally, the shift lowered the marginal cost of each high-quality interaction while improving reliability. Agent handoffs to sales or support became intentional rather than reactive, and insights from conversations fed directly into product discovery. That closed feedback loop informed roadmap decisions and sharpened our go-to-market strategy.
If you are considering a similar move, start with a clear AI Strategy tied to measurable outcomes, a robust governance model, and a pragmatic rollout plan. Focus the agent on high-intent moments first, surround it with analytics and experimentation, and let the data guide expansion. The goal is not to replace humans—it is to elevate them by letting the AI Agent handle the repetitive, high-volume work so your teams can focus on complex, high-value interactions.
Every week I meet teams eager to unleash AI-driven personalization across their products—and I share the same excitement. The promise is magnetic: experiences that feel tailor‑made, delivered at scale, and continuously optimized. Yet sustainable differentiation doesn’t come from turning every dial to eleven; it comes from clarity of intent, responsible design, and disciplined execution.
AI has us on the verge of a new age of ultra-personalized digital product experiences. But don't swing too big too early.
When I think about “how far is too far,” I anchor on user trust, explainability, and measurable value. If a personalization can’t be explained in a sentence, verified through A/B testing, or opted out of without friction, it’s a risk to both brand and product-market fit. The goal isn’t maximal personalization—it’s meaningful personalization that compounds retention and strengthens the value proposition.
I start with product discovery basics: who are the core segments, what jobs-to-be-done matter most, and where does personalization remove friction or accelerate time-to-value? That focus informs pragmatic AI Strategy. Instead of boiling the ocean, I’ll select one high-traffic, high-intent flow and define the precise outcome we want to move. Then I set outcomes vs output OKRs and instrument the path so I can track lift, variance, and trade-offs in real time.
Data governance is non-negotiable. Consent, transparency, and data minimization create the foundation for scalability. I document what signals power personalization, how long they persist, and who can access them. Strong governance isn’t a brake; it’s an enabler, letting us expand confidently without rework or reputational drag.
From there, I validate with A/B testing and clear minimum detectable effect (MDE) thresholds. Holdouts, guardrail metrics, and cohort analyses keep me honest. I’ll use Amplitude analytics to examine funnel impacts, retention analysis, and segment-level effects—especially to ensure we’re not improving conversion while harming long‑term engagement or fairness for smaller segments.
Early wins often come from onboarding and in-app guides. Personalizing the first five minutes—recommended next steps, contextual tooltips, or a tailored product tour—can deliver a step-change in activation with minimal risk. This is where product-led growth shines: relevant, timely nudges that shorten the path to the “aha” moment without feeling intrusive.
As we scale, gen ai and agentic AI open new frontiers. I’ve had success with assistants that proactively summarize account health, suggest next actions, or auto-draft content using the customer’s tone. But I always ship with transparency (“Why am I seeing this?”), controls (easy snooze or opt-out), and fallbacks (graceful degradation if signals are sparse). The human is still the hero; AI should play the role of a reliable, explainable copilot.
My implementation roadmap follows a crawl‑walk‑run arc. Crawl: rules‑based personalization in one journey; clear metrics and opt‑out. Walk: contextual recommendations using embeddings and feedback loops; continuous A/B testing. Run: agentic workflows that take multi‑step actions with approval gates and audit trails. Each phase is gated by evidence, not enthusiasm.
Finally, I treat personalization as a living system. I review dashboards weekly, continuously prune features that add complexity without durable lift, and socialize learning across product trios and empowered product teams. When personalization stays grounded in outcomes, ethics, and craftsmanship, it stops feeling “creepy” and starts feeling inevitable.
Personalization is not a stunt; it’s a capability. Build it with intention, measure with rigor, and earn the right to go deeper over time.
Inspired by this post on Amplitude – Perspectives.
I’ve learned the hard way that experiments stall when they’re treated like items to check off a backlog. Real impact shows up when experimentation becomes the way we think, plan, and decide—every day, across the entire product organization.
Successful experimentation isn't just about adopting new tools or running more tests. It’s about changing company culture.
At HighLevel, I anchor experimentation in outcomes, not output. We form product trios and empower product teams to own the problem, link work to outcomes vs output OKRs, and commit to fast learning loops. This isn’t about more activity; it’s about better decisions, tighter focus, and measurable customer value.
Our teams write crisp hypotheses, define decision rules up front, and set a minimum detectable effect (MDE) before any A/B testing begins. That small discipline prevents “result fishing,” speeds up decisions, and aligns everyone on what will constitute a real signal versus noise.
Tooling helps, but only when it serves the culture. We instrument experiences end-to-end, lean on Amplitude analytics within a unified analytics platform, and run retention analysis alongside acquisition metrics so we don’t celebrate shallow wins. The goal isn’t dashboards; it’s actionable insight that improves product-market fit lessons and informs the next iteration.
Rituals make the culture durable. We review experiments weekly, tie learnings back to OKRs during QBRs, and celebrate invalidated hypotheses as progress. That psychological safety turns “being wrong” into momentum, reinforcing product management leadership behaviors we want to scale.
We also invest in decision hygiene: clear problem statements, pre-registered success criteria, and simple templates that make it easy to do the right thing quickly. Over time, this reduces debate theater and increases the surface area for discovery—more time with customers, more signals, and more conviction in our bets.
If you’re starting from scratch, begin small: pick one critical journey, articulate a hypothesis, choose a primary metric and MDE, run a lean A/B test, decide ahead of time how you’ll act on outcomes, and close the loop publicly. Repeat that cadence until it becomes muscle memory. That’s how experiments stop being one-off projects and start compounding into product-led growth.
When experimentation is a culture, not a task, teams move faster, leaders make clearer tradeoffs, and customers feel the difference. That is the habit I continue to build—one hypothesis, one decision rule, and one learning loop at a time.
Inspired by this post on Amplitude – Perspectives.
