Category: IT Leadership

Pendo Admin Power Checklist: 4 Proven Practices to Drive Adoption, Clarity, and Trust

Overseeing complex platforms like Pendo is where product leadership comes to life. I rely on four disciplined practices to keep our instrumentation clean, our in-app experiences on-brand, and our analytics credible enough to guide high-stakes decisions. If you’re setting up or tuning your instance, this checklist will help you build trust with stakeholders and accelerate product-led growth.

Learn best practices that every Pendo admin should know.

1) Standardize tagging and taxonomy. I start by defining a clear naming convention for feature tags, page tags, and track events (for example, feat:[area]:[action]). This taxonomy lives in a shared document, aligns to our product roadmapping and sprint planning, and includes ownership, definitions, and “do/don’t” examples. In practice, this reduces duplicates, improves segment reliability, and makes funnels, paths, and retention analysis far more actionable. I also schedule quarterly hygiene to retire stale tags and revalidate critical measures tied to OKRs.

2) Segment deliberately and manage access with intention. Meaningful segments—role, lifecycle stage, plan tier, and account health—unlock precise targeting for in-app guides and stronger insights. On the admin side, I enforce least-privilege access with SSO/SCIM, audit changes to tags and guides, and keep visitor and account ID strategies consistent across environments. This combination strengthens data governance and privacy-by-design while reducing operational risk.

3) Operationalize a guide lifecycle. In-app guides are powerful, but only when they’re coherent and governed. I maintain a style system and reusable templates for tooltips, walkthroughs, onboarding checklists, and the Resource Center so the UX feels intentional, not noisy. Every guide goes through QA in staging, frequency capping, sunset dates, and an owner accountable for outcomes. I measure impact with clear success metrics—adoption lift, funnel completion, or onboarding time—to ensure guides serve the product strategy, not just add UI clutter.

4) Build an analytics cadence that leaders can trust. I treat Pendo as a decision system, not just a dashboard. That means SDK updates are part of our release checklist, known key events are smoke-tested after deployments, and weekly insight reviews turn funnels, paths, and retention analysis into clear actions. Where appropriate, I pair experiments with A/B testing guardrails and tie findings back to outcomes vs output OKRs. Finally, I publish a simple “what we learned” summary to keep stakeholders aligned and focused on the next best move.

Your 5‑minute checklist: confirm a shared tagging taxonomy; align segments to roles, lifecycle, and plans; apply least-privilege access and SSO/SCIM; standardize guide templates and QA; set metrics for every guide; and establish a recurring analytics review tied to OKRs. With these four practices in place, your Pendo instance becomes a flywheel for onboarding, product adoption, and continuous discovery—without sacrificing governance or customer trust.

If you’re scaling quickly, start small: pick one product area, instrument it cleanly, launch a targeted in-app guide, and run a focused funnel review the following week. Momentum builds when teams see crisp insights and customers feel helpful guidance at just the right moment.

Inspired by this post on Pendo – Best Practices.

October 25, 2025
SXM vs. the Rest: My High-Impact Playbook for Today’s Software Experience Tools and PLG

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.

Inspired by this post on Pendo – Best Practices.

October 25, 2025
The 5 Stages of Software Experience Maturity: What to Fix First to Unlock Growth

I’ve led product teams through chaotic launches, painful plateaus, and breakout growth, and one truth keeps showing up: software wins when the experience is intentionally designed, measured, and continuously improved. To make that work repeatable, I rely on a simple maturity framework that aligns our product strategy, analytics, and in-app experience work across the organization. Find out where you stand—and what to fix first—with this maturity framework. Why “software experience” and not just “features”? Because activation, adoption, and retention depend on how clearly users understand value in their first sessions, how seamlessly they complete key workflows, and how consistently they succeed over time. That’s where empowered product teams, product-led growth, and outcomes vs output OKRs come together to create durable results. Stage 1 — Ad Hoc: At this level, teams ship features without a clear sense of who benefits, how success is measured, or how UX writing and onboarding shape outcomes. If this is you, fix this first: define your activation events, instrument the core funnel, and write concise, in-product copy that reduces friction. Even a lightweight retention analysis will reveal where value drops off. Stage 2 — Instrumented Awareness: You’ve added basic analytics and can see signups, activations, and drop-offs, often via tools like Amplitude analytics or a unified analytics platform. What to fix first: translate raw metrics into hypotheses and prioritize a small set of A/B testing experiments. Use a minimum detectable effect (MDE) to size tests, and start tracking leading indicators tied to adoption—not vanity metrics. Stage 3 — Guided Journeys: Onboarding, in-app guides, product tours, and contextual tooltips now clarify value and reduce time-to-first-value. What to fix first: build a guided path to activation for your top two personas, then test microcopy and sequencing. Pair qualitative insights from user feedback with cohort-based retention analysis to ensure your guides create durable behavior change, not just clicks. Stage 4 — Outcome-Driven Execution: Teams set outcomes vs output OKRs, run disciplined experiments, and connect learnings to roadmap decisions. What to fix first: standardize an experimentation playbook with clear guardrails for MDE, sample sizing, and stop rules. Align quarterly bets with a value proposition narrative that ties product discovery to measurable, customer-centric outcomes. Stage 5 — Predictive and Proactive: You anticipate user needs with tailored experiences, automate nudges at the right moments, and systematize continuous discovery. What to fix first: unify data across product, support, and lifecycle channels to personalize experiences without eroding privacy-by-design. Invest in scalable governance so insights flow to product trios and forward deployed engineers quickly and safely. How to use this framework: honestly score your current stage across analytics, onboarding, guidance, experimentation, and decision-making. Then pick the single change that removes the biggest bottleneck to the next stage—often a measurement gap, not a feature gap. Make improvements visible through product roadmapping and sprint planning, and celebrate progress to reinforce empowered product teams. In practice, maturity is not a badge; it’s a habit. When we pair rigorous analytics with thoughtful in-app experiences and clear strategic outcomes, we compound learning and unlock growth. If you’re unsure where to begin, start small: instrument activation, improve one critical guide, and run one high-quality experiment. Momentum follows.

Inspired by this post on Pendo – Best Practices.

October 25, 2025
How I Scale Revenue with Pendo Predict: Cut Costs, Reduce Risk, and Drive Product Adoption

When my team and I set out to accelerate growth without ballooning costs, we leaned into Pendo Predict as a keystone of our product-led growth strategy. Predict gives us a practical, data-driven way to focus on the right users at the right moments, align teams around measurable outcomes, and turn product usage signals into revenue impact.

“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.” That statement maps exactly to how we operate: we use the platform to understand user behavior, guide users through high-value actions, and instrument the experience so we can learn, iterate, and scale with confidence.

To scale revenue, we identify high-intent segments based on product behaviors and run targeted in-app guides and product tours that shorten time-to-value and boost conversion. Predict helps us surface which features correlate with expansion and retention, so our onboarding flows nudge users into those paths. This approach compounds: better activation drives stronger engagement, which fuels a healthier pipeline for cross-sell and upsell.

On the cost side, we reduce support load with contextual guidance—tooltips, checklists, and just-in-time education—so customers self-serve through common friction points. We consolidate insights in a unified analytics platform, enabling product, success, and go-to-market teams to work from the same source of truth. The result is fewer reactive escalations, tighter prioritization, and more engineering time invested in features that move retention and revenue.

Risk reduction comes from visibility and control. With predictive signals and retention analysis, we spot churn risk early, intervene with timely in-app messaging, and de-risk launches by rolling out features to targeted cohorts while monitoring adoption and engagement. We pair this with disciplined experimentation and A/B testing to validate changes before scaling broadly.

If you’re considering a similar motion, a simple playbook works: define your adoption and engagement metrics, instrument key workflows, create predictive segments, ship focused in-app guides, and measure impact against outcomes—not just outputs. Over time, this turns your product into a durable growth engine that consistently improves user experience and business performance.

Inspired by this post on Pendo – Best Practices.

October 24, 2025
SaaS + AI Is Here: How Our Summer 2025 Release Builds an Intelligent Foundation to Win

Leading product at HighLevel, I’m watching the convergence of SaaS + AI reshape how we build, price, and scale software. The winners will combine a sharp AI Strategy with disciplined product management leadership to ship real outcomes, not just demos. That’s why my team and I have been focused on giving you pragmatic ways to move fast without breaking trust. Give your company an intelligent foundation for the SaaS + AI era with our Summer 2025 Release. When I set priorities for this release, I optimized for three things: speed with quality, responsible AI, and measurable business impact. Practically, that means enabling agentic AI and gen ai workflows where they actually create leverage, unifying analytics so teams can make decisions from a single source of truth, and hardwiring data governance and privacy-by-design into every layer. If you’re wondering how to keep up, here’s what’s working for us and our customers: tighten product roadmapping and sprint planning around clear outcomes, not outputs; align teams with simple, observable OKRs; and empower product trios to run lean product discovery loops. These practices reduce cycle time while raising confidence, especially when introducing AI into core experiences. On the go-to-market side, I’m doubling down on product-led growth—shipping value into the product with in-app guides, thoughtful product tours, and frictionless onboarding. Pair that with rigorous retention analysis and A/B testing, and you’ll see which AI-powered moments actually move activation, adoption, and expansion. Don’t overlook the fundamentals either: smart SaaS pricing (including consumption models where it fits) can unlock the economics that sustain AI investments. My goal is to give you a foundation that is both ambitious and accountable—a platform you can trust to scale responsibly while your teams iterate quickly. If you’re planning your 2H roadmap, this release is built to help you ship faster, de-risk AI, and create outsized customer value in the moments that matter most.

Inspired by this post on Pendo – Perspectives.

October 24, 2025
3 Powerful Ways AI Is Reshaping Cybersecurity—from Ruthless Attacks to Rapid Defense

Every week, I watch the cybersecurity landscape bend under the pressure of AI. The pace isn’t linear—it’s compounding. What worked for IT teams last quarter often needs a rethink today, and the difference between merely coping and truly competing lies in how quickly we adapt our strategy, tooling, and operating rhythms.

Learn the ways in which AI is transforming both cybersecurity offense and defense for IT teams.

From my vantage point leading product strategy, I see three shifts that matter most right now: AI is supercharging attackers, accelerating defenders, and reshaping governance. Together, they redefine how we prioritize investments, measure risk, and align product and security roadmaps.

First, AI has leveled up the offense. Large language models can industrialize social engineering—hyper-personalized spear-phishing at scale, deepfake voice notes that spoof executives, and highly convincing support chats that trick users into bypassing controls. Code-generation tools lower the barrier to crafting polymorphic malware and automating reconnaissance. The net effect is ruthless efficiency: more credible lures, faster campaigns, and broader reach with fewer human operators. I now assume adversaries have an AI co-pilot—and plan defenses accordingly.

Second, AI is accelerating the defense. Modern detection and response stacks are moving beyond rules to behavioral analytics—correlating identity signals, endpoint telemetry, and network events to spot subtle anomalies that signature-based tools miss. Copilot-style assistants are augmenting SecOps by summarizing incidents, explaining probable root cause, and proposing next steps. The aim isn’t blind automation; it’s decision acceleration—shrinking mean time to detect and respond while reducing analyst toil. On the build side, AI-assisted code scanning and dependency analysis help teams shift security left, catching vulnerabilities earlier and turning secure defaults into muscle memory.

Third, governance is being rewritten in real time. As AI models ingest sensitive data and generate code and content, data governance and privacy-by-design move from compliance checklists to active risk management. We’re formalizing AI risk management alongside traditional AppSec: model inventories, usage policies, red-teaming prompts, and guardrails against prompt injection and data leakage. Identity remains the control plane—zero trust principles, least privilege, and continuous verification become nonnegotiable. I’ve found that aligning security, product, and IT leadership on a single policy-as-code backbone prevents drift and keeps audits predictable.

Practically, I guide teams to start with a crown-jewel inventory: What data and systems would materially impact customers, revenue, or brand if compromised? Map data flows, instrument comprehensive telemetry, and prioritize detection coverage where it matters most. Choose AI to augment before you automate—prove the loop with humans in the middle, then graduate to higher autonomy levels with clear rollback paths and audit logs.

Culturally, this is a product problem as much as a security one. We bring empowered product teams and SecOps into the same room, set measurable objectives (signal-to-noise ratio, mean time to contain, escaped defect rate), and iterate with the same cadence we use for product features. When security outcomes are treated as customer outcomes, adoption soars and friction recedes.

The takeaway: AI has tilted the field, but not inevitably against defenders. With a clear AI strategy, disciplined data governance, and pragmatic automation, IT leaders can turn reactive security into a proactive advantage—meeting attackers’ speed with speed, and outlasting them with better judgment.

Inspired by this post on Pendo – Perspectives.

October 24, 2025
4 Hidden AI Risks Every CIO Must Tackle Now—and a Proven Playbook to Mitigate Them

Across enterprises, I’m watching AI sprint from lab experiments to business-critical workflows. That velocity is exciting—and it’s also where risk compounds. In my role partnering with CIOs and IT leadership, I’ve learned that winning with AI is as much about disciplined risk management as it is about breakthrough use cases.

Learn about the risks that AI poses to IT teams, and how they can mitigate them.

I frame the challenge as “4 AI risks for CIOs (and a guide to solve them)”: data governance and compliance, model reliability and bias, security and supply chain exposure, and operational cost/ROI drift. Below, I outline the risks I see most often and the concrete actions I take to de-risk them without slowing innovation.

Risk 1: Data governance and compliance. The fastest way to stall an AI Strategy is to overlook consent, lineage, and access controls. I establish privacy-by-design from day one: data minimization, clear retention policies, role-based access control, and auditable logs for training, inference, and feedback loops. I also insist on defensible vendor reviews (DPA, SOC2/ISO, regional data residency), PII classification, and internal model cards that document sources, sensitivities, and acceptable-use constraints. This makes IT leadership comfortable scaling from prototype to production.

Risk 2: Model reliability, hallucinations, and bias. AI that fabricates or skews output erodes trust and creates downstream risk. I operationalize quality with evaluation harnesses, golden datasets, human-in-the-loop review for high-impact actions, and red-teaming for safety. Retrieval-augmented generation with citations, content filters, and grounded prompts reduce error rates. To quantify progress, I define precision/recall targets and a minimum detectable effect (MDE) for experiments so we know when a change is truly better—not just different.

Risk 3: Security and AI supply chain. New surface area invites prompt injection, data exfiltration, and compromised dependencies. I apply zero-trust principles: strict allow/deny lists for tools and connectors, secrets isolation, egress controls, sandboxed environments for agents, and output validation before execution. Every model and plugin goes through threat modeling, dependency scanning, and vendor security reviews. For agentic AI patterns, I gate high-risk actions behind explicit approvals and granular scopes.

Risk 4: Operational cost and ROI drift. AI workloads can balloon with hidden inference costs, shadow IT, and duplicated platforms. I put governance around spend using consumption SaaS pricing guardrails, usage caps by environment, tagging by app/team, and a unified analytics platform to monitor latency, quality, and cost per transaction. This lets me reallocate budget toward the highest-impact use cases while sunsetting low-yield experiments.

Your 90-day playbook. Days 0–30: Inventory AI use cases, classify data sensitivity, choose one or two critical business workflows, and stand up core guardrails (access, audit, red-teaming). Days 31–60: Pilot with a cross-functional product trio (PM, design, engineering), define OKRs, instrument evaluations, and enable human-in-the-loop. Days 61–90: Productionize the winning flow, set usage and spend policies, enable observability dashboards, and roll out training for frontline teams with clear escalation paths.

The organizational layer matters as much as the technical one. I align stakeholders early, empower product trios to iterate quickly within boundaries, and deploy forward deployed engineers to embed with the business. This keeps trust high, reduces handoffs, and ensures that governance accelerates value rather than blocking it.

Done well, these practices turn AI risk into a competitive moat. By pairing disciplined governance with pragmatic experimentation, we capture the upside of gen ai while protecting customers, teams, and the business. That’s how I’ve helped enterprises move from scattered pilots to measurable, scalable impact—safely.

Inspired by this post on Pendo – Perspectives.

October 24, 2025
Our Pendo-Powered Playbook: Orchestrating a High-Impact Summer Release with Product-Led Growth

We set out to promote the Pendo Summer Release using the most authentic approach possible: we used Pendo to market Pendo. That decision anchored our strategy in product-led growth, letting us reach users in context, guide them through new capabilities, and measure impact in real time without adding friction or cost.

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.

Our objectives were clear: drive adoption of new features, accelerate onboarding for existing customers, and improve engagement across key workflows. We framed the work with outcomes vs output OKRs, clarified the value proposition for each persona, and aligned our product positioning to highlight points of parity and genuine differentiation.

Execution centered on in-app guides, product tours, and purposeful tooltip design. We segmented by role, lifecycle stage, and behavior to keep messages timely and relevant, then layered in A/B testing with a defined minimum detectable effect (MDE) so we could learn fast without overexposing users. Product trios partnered closely with design and forward-deployed engineers to iterate quickly on copy, UX writing, and guide placement.

On the measurement side, we instrumented clear goals and tracked conversions through the funnel, pairing event analytics with retention analysis to understand depth of usage, not just clicks. We captured qualitative signal through micro-surveys and in-context feedback, feeding insights back into product roadmapping and sprint planning to sharpen our next set of in-app experiments.

Governance mattered as much as growth. We applied privacy-by-design principles, ensured strong data governance, and kept stakeholder management tight so each guide had a clear owner, sunset plan, and success criteria. That discipline helped us sustain momentum without cluttering the experience.

The biggest lesson: when done thoughtfully, in-app education scales like a dedicated success team—at a fraction of the cost—while teaching you exactly where users find value. This Pendo-powered launch playbook now underpins our onboarding, cross-sell motions, and QBRs alike, giving us a repeatable way to promote releases, validate hypotheses, and deepen engagement with every iteration.

Inspired by this post on Pendo – Perspectives.

October 24, 2025
How Pendo Agent Analytics Protects Your Data—and Accelerates Adoption Without Compromise

Protecting customer data while driving product-led growth is the needle I move every day. When I evaluate analytics agents for enterprise software, I look for platforms that make it easy to learn from behavior without exposing sensitive information. That is the promise behind Pendo Agent Analytics: actionable insight with strong guardrails, so teams can move fast without breaking trust.

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.

In practical terms, “protecting your data” starts with privacy-by-design: data minimization, clear event taxonomies, and opinionated defaults that discourage collecting anything you don’t need. I require role-based access controls, transparent governance workflows, and a unified analytics platform that helps product, engineering, security, and legal speak the same language. Those foundations enable confident experimentation—A/B testing, onboarding optimizations, and in-app guides—without creating new risk.

My implementation playbook is straightforward. First, define a lightweight tracking schema aligned to outcomes (adoption, time-to-value, retention analysis), not vanity metrics. Second, keep payloads intentionally sparse and free of secrets—no tokens, no free-form text, no PII. Third, ship value quickly with curated product tours and tooltip design that guide users through high-intent moments. Finally, review events regularly with a cross-functional product trio to prune, consolidate, and govern.

Security and data governance are not just checkboxes; they are operating disciplines. I partner with IT leadership to verify access policies, audit usage patterns, and ensure consent and data retention practices meet internal standards. This creates the right tension between speed and safety, so teams can optimize onboarding and in-app experiences while reducing operational risk.

I also benchmark instrumentation approaches across tools—looking at Amplitude analytics, for example—to ensure our event taxonomy and governance model stays consistent across the stack. Consistency matters: it improves stakeholder management, accelerates product discovery, and keeps our outcomes vs output OKRs anchored to the same source of truth.

The result is a healthier product loop: cleaner data, clearer insights, and faster iterations that meaningfully improve engagement. With disciplined governance and thoughtful design, Pendo Agent Analytics can inform what to build next while respecting user privacy—giving teams the confidence to learn at speed, and customers the confidence to keep trusting us.

Inspired by this post on Pendo – Perspectives.

October 24, 2025
Why Winning Product Teams Obsess Over the First 5 Minutes to Drive Retention and Growth

The first five minutes a new user spends in a product set the trajectory for everything that follows. In my experience, that brief window determines activation, early retention, and ultimately whether product-led growth compounds—or stalls. That’s why I obsess over it, instrument it deeply, and treat it as the highest-leverage part of the product experience.

Learn how data-driven teams optimize the first 5 minutes of product experience to improve activation, retention, and growth—and how they do it with Amplitude.

Here’s the practical reason the first five minutes matter so much: users are deciding whether your value proposition translates into an immediate “aha moment.” If time-to-value is long or the path is confusing, activation rate drops, retention curves decay faster, and every subsequent dollar of acquisition becomes less efficient. When we design onboarding intentionally, we shorten the cognitive distance to that first success and build habits that sustain retention.

My playbook starts with measurement. I use Amplitude analytics as a unified analytics platform to instrument the first-run experience end to end, define a clear activation event, and track the user’s journey with funnels, cohorts, and retention analysis. That clarity lets me see where friction spikes, where users hesitate, and which paths correlate with long-term engagement. Without that visibility, changes to onboarding are guesses rather than decisions.

From there, I run disciplined A/B testing. We establish a minimum detectable effect (MDE) based on traffic and variance, and we prioritize experiments that reduce effort to reach the first outcome: simplifying sign-up, clarifying the primary CTA, or pre-seeding a workspace with smart defaults. When we can quantify impact on early activation and downstream retention cohorts, the team can make confident trade-offs and move faster.

Guidance within the product is just as important as the flow itself. Thoughtful UX writing, contextual tooltips, and concise in-app guides should highlight the one or two actions that create immediate value—not overwhelm with a product tour that tries to teach everything at once. The goal is a path to progress, not a lecture. When we pair minimal friction with timely cues, users self-propel to value.

I still remember watching session replays of new users pausing at a crowded first screen. That moment reshaped our approach: fewer choices, clearer hierarchy, and progressive disclosure. The result was a meaningful lift in activation and steadier retention curves. It reinforced a simple truth—when the first five minutes feel effortless, users stick around to explore everything else.

This is also an organizational discipline. Empowered product teams—PM, design, and engineering working as a product trio—align on outcomes vs output OKRs and treat the first five minutes as a shared responsibility. We close the loop with customer feedback, run rapid product discovery, and bring forward deployed engineers into research to shorten the distance between insight and iteration.

If you’re getting started, focus on five moves: instrument the first-run journey in Amplitude analytics; define and track a crisp activation event; analyze funnels and retention cohorts to locate friction; ship weekly A/B tests with a sensible MDE; and iterate your onboarding with lightweight product tours, tooltips, and in-app guides. Tie improvements to leading indicators of product-led growth so the impact is visible to stakeholders across go-to-market and product.

The obsession with the first five minutes isn’t dogma—it’s a commitment to user success. When we reduce friction, spotlight value, and measure what matters, activation climbs and retention compounds. And with the right analytics foundation, we can make those first few moments predictably great, not accidentally good.

Inspired by this post on Amplitude – Best Practices.

October 24, 2025
Why Retention Wins: The Ultimate Product Strategy to Shape Your Roadmap and Ignite Growth

I keep coming back to one simple truth in product management: Retention Is the Ultimate Product Strategy. When customers stay and expand, it signals that we are repeatedly solving real problems with a value proposition strong enough to withstand time, alternatives, and change.

Retention reveals if your product delivers lasting value. Learn how top product leaders use it to guide strategy, shape roadmaps, and drive growth.

At HighLevel, I treat retention as the clearest signal of product-market fit quality and the most reliable compass for product-led growth. I review retention weekly, cohort it by segment and plan, and tie it directly to value moments in onboarding and activation. If we can’t see where users succeed (or stall), we can’t shape a roadmap that consistently compounds value.

Here is how I put retention at the center of product strategy. When cohorts are strong, I double down on the experiences and workflows that create habit loops and advocacy. When cohorts drop, I stop chasing surface-level outputs and run focused product discovery to clarify the value proposition, reduce time-to-first-value, and reset outcomes vs output OKRs so teams are solving for the right problems.

I then translate retention insights into product roadmapping and sprint planning. Every roadmap theme must map to a retention driver: faster activation, deeper engagement, or expanded breadth of use. I use A/B testing to validate critical UX decisions, and I guard against false positives by aligning experiments to business outcomes tied to retention, not just clicks or vanity metrics.

Instrumentation matters. I rely on Amplitude analytics to trace the path from first touch to recurring value, measuring drop-offs, leading indicators of habit formation, and usage cliffs by persona. With clean event data, I can connect improvements in onboarding to cohort lift and quantify what features actually move long-term retention, not just short-term engagement.

Most retention gains come from the “boring but pivotal” basics: a frictionless onboarding flow, clear in-product guidance, and a crisp path to the first “aha” moment. I continually refine these with targeted improvements, then reinforce them with contextual education and lifecycle touchpoints that help customers unlock the next milestone of value.

I also segment retention to find hidden opportunities. Different plans, industries, and team sizes have distinct activation thresholds and success criteria. By tailoring experiences and success metrics per segment, we avoid one-size-fits-all decisions and build for real-world diversity while still maintaining a coherent roadmap.

Culturally, retention is how I keep product management leadership grounded. It forces ruthless prioritization, sharpens stakeholder conversations, and aligns teams on outcomes. When teams see their work reflected in month-over-month cohort lift, motivation rises—and so does our confidence in the strategy.

If you’re looking to operationalize this approach, start with a baseline retention analysis, define your key value moments, align a handful of outcomes vs output OKRs to activation and engagement, instrument the journey in Amplitude analytics, and prioritize one or two onboarding improvements that shorten time-to-first-value. Ship, measure, and iterate. Over time, this creates a roadmap that writes itself from the evidence of durable customer value.

Inspired by this post on Amplitude – Best Practices.

October 24, 2025
Build vs. Buy in Experimentation: Why Embracing Vendors Accelerates Real Innovation

For much of my career, I reflexively favored building experimentation tooling in-house. Over the last few years, I’ve changed my mind. The ecosystem has matured, the bar for statistical rigor has risen, and the opportunity cost of reinventing the wheel has become too high to ignore. Read why the industry has changed to more broadly embrace vendor solutions—and why that's a good thing for innovation.

The short version: buying core experimentation capabilities increasingly lets us learn faster, reduce risk, and focus scarce engineering cycles on true differentiation. I still believe in building when it creates competitive advantage, but I’ve seen too many teams burn time on “table stakes” infrastructure instead of delivering outcomes that matter.

When I evaluate build vs. buy, I start with two questions: Is this capability a point of parity or a source of competitive differentiation? And what is the real total cost of ownership over three years, including staffing, maintenance, on-call, compliance, roadmap drag, and delayed time-to-learning? Most experimentation platforms are now points of parity; the differentiation is how quickly and responsibly we learn, not whose statistics package we forked.

Modern experimentation isn’t just a split URL test. It demands identity resolution across devices, reliable bucketing, exposure logging at scale, edge delivery for flags, guardrail metrics, and rigorous methods like minimum detectable effect (MDE), CUPED, and sequential testing. Add privacy requirements, data governance, and auditability, and the platform burden grows beyond a “quick internal tool.” This is exactly where vendors have pulled ahead, baking in best practices we’d otherwise relearn the hard way.

There are still good reasons to build. If you operate under unique latency constraints (e.g., sub-20ms decisions at the edge), have non-negotiable regulatory boundaries, or your experimentation model is deeply coupled to proprietary ML systems, bespoke tooling can be justified. I’ve supported builds in those cases—but only with a clear plan for long-term ownership, documentation, and explicit trade-offs.

More often, buying is the sane default. Vendor solutions give us hardened SDKs, consistent flagging, proven stats engines, and integrations with analytics—freeing teams to spend their energy on high-quality hypotheses and better product discovery. Connecting experiment outcomes to a unified analytics platform (and tools like Amplitude analytics) helps us align on source-of-truth metrics, tighten feedback loops, and empower product trios to make confident, outcome-driven decisions.

A hybrid approach frequently wins: buy the platform core, then extend it. Build custom decisioning services where needed, enrich telemetry, and add domain-specific metrics on top. I’ve had success pairing vendor platforms with forward deployed engineers and thoughtful developer evangelism to create the best of both worlds—speed from the vendor, nuance from our domain.

If you’re considering a shift, here’s the adoption playbook I use: – Define success upfront: decision latency targets, MDE guidance, guardrail metrics, governance needs, and privacy constraints. – Run a time-boxed pilot with an A/A test and a handful of A/B testing use cases. Validate exposure logging, bucketing stability, and metric parity against your analytics stack. – Align on outcomes vs output OKRs, so “more experiments” is never the goal; better decisions are. – Establish data governance and metric definitions before full rollout. Treat metrics as a product, not a spreadsheet. – Invest in enablement: in-app guides, product tours, and training for PMs, engineers, and analysts. Proactive stakeholder management is what separates a successful rollout from shelfware.

AI is accelerating this shift. Gen AI for product prototyping and agentic AI assistants can help generate hypotheses, auto-suggest experiment designs, and flag risky rollouts in real time. Pairing AI with a robust experimentation backbone improves both velocity and quality—without asking teams to become statisticians overnight.

My bottom line: the industry’s embrace of vendor experimentation platforms is not a retreat from craftsmanship—it’s a strategic allocation of talent. By buying where the market is excellent and building where our differentiation truly lives, we learn faster, reduce risk, and compound innovation. If you haven’t revisited your build vs. buy calculus recently, now is the time. Your customers don’t reward you for owning a stats engine; they reward you for shipping better outcomes, sooner.

Inspired by this post on Amplitude – Perspectives.

October 24, 2025