Roshan Gupta

One of the sneakiest product blind spots I help fix as a fractional CPO: the hidden cost of poor prioritization. On the surface, “let’s just build a few more features” feels harmless. In reality, it quietly drains teams in four ways: - Opportunity cost: every “yes” to a low-ROI idea delays the high-impact work - Context switching: teams lose momentum and velocity when priorities keep changing - Tech debt: rushed features become future rework that eats runway - Morale: shipping things users ignore is one of the fastest ways to demotivate a team I’ve seen companies burn 3–6 months (and a lot of cash) simply by chasing the wrong things. A simple antidote that works: RICE scoring + a quarterly roadmap lock-in (with a clear “change control” rule). Founders / product leads: What’s the biggest opportunity cost you’re paying right now because priorities are scattered? Reply here, or DM me if you want to talk through your situation. I’m open to a few fractional CPO engagements for 2026. #ProductManagement #Prioritization #FractionalCPO #Startups #Growth #Leadership

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Product Marketing friends! Could your launch comms use a tune up? Read on. Adam O'Brien is the host and creator of the brand new, excellent Product Marketing for You podcast (I'll be on it soon!). He's looking for people to submit product launch emails for him and one of his guests to dissect on the pod, with the goal of giving you actionable feedback to improve your launches. And I promise they'll do it kindly. This is a great opportunity to get out of launch tunnel vision and get an outsider's perspective. I think this would be especially useful for solo PMMs who may not have someone to bounce ideas off and has gotten into a 'rinse and repeat' rut. Feedback is a gift, even if it's sometimes uncomfortable. More details in Adam's post below 👇

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There Are Two Kinds of Product People in This World, My Friend: Those with Evidence, and Those Who Complain In professional product communities, certain stories are inevitable. They unfold the same way: the market is broken, hiring is absurd, feedback is misdirected, tools are clumsy, and everything conspires against the author. Often—though not always—these tales rely on sweeping generalizations: “all of Europe,” “any fintech,” “every corporation,” “the whole of crypto.” Both threads—the lament and the overgeneralization—quietly erode professional credibility. Together, they reveal not wisdom or experience, but a simpler truth: the speaker lacks the skills that distinguish a competent product manager from a merely frustrated one. At its core, the work of a product manager and their team comes down to two responsibilities. First: observe how a specific slice of reality actually functions. Second: propose a solution to a particular problem within that slice. Both depend on an unglamorous rhythm: we tried, it failed; we tried again. Over and over. A product manager must be psychologically prepared for failure as the default, not the exception—this is the soft-skills side of the role. They must also structure research and solution-building so that each failure yields insight rather than despair—this is the hard-skills side. The boundary between the two is blurry, but the pattern is clear. Complaints about life, the market, or “how things are these days” usually signal a soft-skills gap. False generalizations, by contrast, point to a hard-skills deficiency. When outcomes falter, a competent product manager asks what the research or design process failed to capture, rather than shifting responsibility onto external forces. This mindset matters not only during iteration cycles and stakeholder conversations, but also in how one recounts the story afterward, especially in professional settings. False generalization is hardly an advanced intellectual flaw; it is the sort of error covered in an introductory logic class. When a product manager casually deploys such claims publicly, they signal that they do not fully grasp how information, evidence, and data analysis actually operate. There is, tellingly, a reliable inverse test. Every genuinely strong product manager I know begins by carefully defining the exact segment of reality under consideration. Only then do they narrate their story—plainly, almost modestly: this is what we tried; this worked; this didn’t; here’s what we know; here’s what we still don’t. It is a less cathartic way of speaking than complaining. But it is also how good products—and good product managers—are made.

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Prediction: Over the year we’re going to see the “Solo Vengeance Founder” story arc play out. Casualties of mass lay offs, who walked out the door with... - your company secrets - good ideas that stalled under bureaucracy - your weak spots, and internal failures - access to the same insane builder tool set you cut them for - and a motivation that's bigger than money The companies who are cutting, are creating hero (or villain) origin stories. They are going to carve you apart slowly, and have a motivation bigger than any equity package. #Startups #AI #Entrepreneurship #FutureOfWork

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Any product leaders looking at the crazy per-seat costs of Productboard, Aha, etc. and thinking "this feels like something Claude could build on Jira" rather than renewing for an 8% uplift?

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Being the most affordable option in your category is a positioning nightmare. People hear "affordable" and think "limited." Last week Ben Labay from Speero published a benchmark of 22 A/B testing tools. Built on frameworks from Dunford, Wynter, Raskin, and 500+ B2B positioning audits. His finding: the A/B testing category has a differentiation crisis. 86% of tools score 2 or below on Differentiation. 95% score 2 or below on Competitive Distinctness. And I think I know why. Who are you for? What do you replace? Why are you different? We decided to answer those questions publicly. We name competitors. We show pricing. We publish comparison tables. Because buyers are comparison-shopping anyway. Why pretend they're not? That's apparently why Varify scored 28/40. Highest in the set. The only tool to hit 3 on Competitive Distinctness. As being responsible for our GTM - I can tell you: being different sounds great in theory. In practice, it's one of the hardest things to execute. People who saw Varify two years ago still carry that old picture. Prospects hear "affordable" and assume "limited." Being different means constantly educating, constantly proving, constantly pushing against a perception you didn't choose. When we relaunched our homepage last December, that was the moment where it clicked. Everyone in this category is moving toward enterprise packages, hiding pricing behind "talk to sales" buttons, and charging based on monthly tracked users. We went the other way. Listen to our partners and customers. Explain the story. Show what we are doing different. When your tool charges per MTU, what do most companies do? They buy less quota or pay more for the tool. Less quota means fewer learnings. Higher costs means more pressure on the team. And when your testing tool tracks a different than your single source of truth you get discrepancies. Discrepancies lead to one thing: lack of trust in results. I see this constantly. Teams don't stop testing because the tool is bad. They stop because they can't trust the numbers anymore and setting up tests is to dev heavy. Skipping own a/b testing tool tracking removes that entire chain. You scale your experimentation program. Your data stays consistent with your real sources of truth. We are building sth. that's ready for what's coming next. Because when AI-driven experimentation becomes the standard (it is already). The tools that win will be the ones with the best integrations, APIs and the easiest workflows to set up experiments. That's the bet we made. P. S. What made me even happier were the comments under Ben's post: Bas: "Sharp strategy, strong execution — well deserved." Joost: "We've been using them for pretty much all of our clients." Sahil: "Big fan of Varify here." I'm deeply grateful for partners and users like these. ❤️ Here is the link: https://lnkd.in/duu7MaxX 𝗣.𝗣.𝗦. I'll be at OMR next week, if you want to compare setups over a coffee just DM me

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Look at the most successful projects, they have 3 things in common. Product, Narrative, and Timing. And the most important part is finding the right alignment. Product -> Proof Of Value Early stage products need to prove a point. The goal is to prove that your idea has traction and potential. Think about Farcaster. It didn’t try to compete with Twitter on day one It just proved that on-chain identity could work. That single proof unlocked everything else: builders, integrations, capital, and narrative momentum. Solve one real problem → create proof of belief → earn the right to scale. That's the easiest way to build a successful product here.

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I’ve learned the hard way: hustle doesn’t beat ambiguity—systems do. When I’m shipping in high-ambiguity environments (new product, shifting requirements, multiple stakeholders), I’ve found that “working harder” rarely fixes the chaos. What does help is treating delivery as three lightweight systems that reinforce each other: 1) Scope system (make the outcome explicit) A short PRD that answers: what problem are we solving, for whom, and how will we know it worked? If the success metric isn’t written down, you end up debating opinions instead of iterating on evidence. 2) Execution system (make progress cheap) A single source of truth backlog with epics → small tickets → clear acceptance criteria. My rule: if it isn’t in the backlog with an owner and a date/sprint, it doesn’t exist. That’s how you avoid “verbal tasks” and quiet drops across parallel workstreams. 3) Quality system (make “done” real) “Done” isn’t “merged.” It’s: acceptance criteria met, edge cases considered, observability in place, and a clear path for rollback/triage if something goes sideways. Quality gates don’t slow teams down—lack of them does, because rework and production thrash are the real velocity killers. None of these systems are heavy. But together, they turn ambiguity into a repeatable loop: define → ship → observe → learn. Curious: what’s the simplest system you’ve seen that keeps teams shipping without losing quality?

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Your AI research tool is the most agreeable colleague you've ever had. That's exactly the problem. LLMs are trained for agreeability and coherence, not accuracy. According to Saul Wyner in UX Magazine, they'll build you a convincing research case for literally anything — including a mashed potato cannon startup called "SpudGun," complete with personas like "The Comfort Craver" and fully synthesized user interviews. The output looked professional. It was structurally perfect. And it was completely meaningless. Here's the problem: AI doesn't challenge your assumptions. It reinforces them. It optimizes for responses you'll agree with, not responses that are true. A polished path of poor reasoning is more dangerous than an obviously bad idea. Because you'll act on it. This is why we're building Seena differently — using AI to augment real user research, not to generate comfortable fictions that look like insights. The future of research isn't AI replacing researchers. It's AI making real human insights faster and more actionable. Join the waitlist at SeenaLabs.io Have you caught AI telling you what you wanted to hear instead of what you needed to hear? #AI #UserResearch #ProductManagement #UXResearch #ConfirmationBias

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Great article from my friend Eva exploring the magic behind product-market fit—especially loved the take on balancing bold ideas with deep customer understanding. It’s a reminder that success isn’t just about building a great product, but about building the right product for the right people. What do you think is the most underrated factor in achieving product-market fit? #ProductMarketFit #Startups #Leadership

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When you buy Rillet, you’re not just buying the product as it is today, you’re buying velocity. We release new features everyday. Here’s the highlights from this week: Aura Flow Scheduling — Build a workflow once, set your cadence, and Rillet runs it automatically. Recurring analyses and reports, no manual effort. I cannot tell you how much this would have saved me as a controller. Export Bank Transactions & Vendor Data — A few clicks to get your data out, whether you're reconciling externally or sharing with your team. Semi-Annual Billing on Contracts — One more billing cadence, more flexibility for how your customers pay. Hybrid Contracts — Usage-based and fixed line items on the same contract. No more splitting deals to make them work. Aura AI: Faster + Bigger Files — Noticeably snappier responses and large Excel file support. File size is no longer a blocker. What should we ship next?

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Looking to land your first Product role? Here are five things you can do this week to get a leg up on the competition. 1️⃣ Pick one of the vibe coding prototype tools and teach yourself how to use it. Doesn’t need to be amazing, and you can just pick your favorite website or app and try to replicate it as closely as possible. I go with Bolt for my own projects and for the cost of an oat milk latte, you’ll have enough credits to get a decent prototype.  2️⃣ Reach out to five second degree connections and ask to have an open-ended chat with them. Brag about yourself and tell them what THEY can learn from you. Not everyone will say yes …. But you’ll find someone that has a little free time and is curious to learn. Reverse mentoring is a thing - don’t assume you don’t have something you can teach. 3️⃣ Reach out to colleagues in other departments and ask them if you can shadow a meeting or help out on one of their projects. I probably learned more about Product by watching OTHER teams work than watching my own team work. Figure out where you can fit in and how you can improve the way different teams work with each other. 4️⃣ Get away from your computer but bring your phone or a small notepad. The shower principle is true. When you turn off your brain, you get your best ideas. So go for a walk, take a yoga class, bring a book to a coffee shop. But jot down your great ideas when they come to you. 5️⃣ Pick a book or a podcast to dive into. Highly recommend Upstream (https://lnkd.in/ekufQJq6) to read and then either Lenny's Newsletter, The Media Copilot, The Product Manager, or Decoder to listen to. Any tips I'm forgetting? Drop em below

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When I joined a city, there was no shared product roadmap for one of the departments I support. Six months later, we have one that aligns the whole department. Here’s how I did it: (I’ll tell you this in 2 minutes) Step 1: Create a list of potential projects to consider The key was making the list visible and collaborative from day one. Here are 3 quick tips to help you master this step: • Let everyone know the list exists. Review it openly with teams and stakeholders. • Gather input, update the list, and keep it in a shared public place. • Understand the department’s annual goals — but resist the urge to edit or prioritize the list too soon. Keep these in mind as you get started. Step 2: Create a rough draft prioritization and share it with stakeholder groups Once I implemented this step with our digital services team and city department, I noticed: • Better alignment across teams • More productive conversations around specific projects and timing • The door stayed open for projects that had been overlooked Sharing early made collaboration much easier later. Step 3: Refine the quarterly roadmap based on timing and team availability. For this step, I dialed in what I was doing in Steps 1 and 2 to improve our confidence in the quarterly roadmap and ensure we were focused on the right things. This is how I built a product roadmap for a city department within 6 months of joining. And how you can too.

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For years, our focus has been on speed — building, shipping, and solving customer problems fast. It’s a great strategy for building a moat around your core business. Moving quickly to support every phase of home construction is how Buildertrend became the #1 construction management platform. But as our platform has grown, UX integrity has also become critical. The consistency, predictability, and quality of our user experience have a direct impact on customer satisfaction and retention. For that reason, our design system can’t just be a set of reusable parts — it has to be the framework that helps hundreds of product people build coherent workflows that instill customer confidence and trust. This shift hasn’t been easy. We've learned that consistency can sometimes feel like constraint — and governance can feel like slowdown. A few reframes that have helped: ❌ Instead of saying: “We need to follow the design system to keep things consistent.” 👉 Say: “We’re protecting UX integrity — a core part of how we deliver customer value at scale.” ❌ Instead of saying: “Engineering needs to use the approved components.” 👉 Say: “Our customers shouldn’t have to learn a new interface pattern every time they use a different feature.” There’s still work to do to make the design system feel inviting to everyone involved. But that’s the journey — UX integrity is how we scale quality, and building it together is what will transform structure into strength.

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When we started OZi, it wasn’t just about solving a market gap, it was about solving something I was living every day as a mom. Like so many parents, I was constantly juggling work, home and the endless decisions that come with raising a toddler. There were plenty of choices, but very little time or clarity. Every purchase meant multiple tabs, second guesses, and far too much effort. OZi was born from that chaos! We set out to build one place where parents could find everything they need, quickly, confidently and without the overwhelm. Because sometimes, convenience isn’t a luxury, it’s essential. Today, OZi brings together 15,000+ thoughtfully curated products across kids fashion, toys, essentials, baby gear, and school supplies. And because we’ve been there, features like ‘Try & Buy’ and ‘At Home Demos’ are designed to make those bigger decisions easier, without stepping out of home. I’m incredibly grateful to share that OZi has raised $6.2M in Series A funding led by RTP Global, with participation from Blume Ventures, Huddle Ventures, Zeropearl VC, and a group of angels and operators who believe in our vision. To the team that builds with empathy and intention every day, thank you! And to the parents who trust OZi, especially the ones navigating the beautiful chaos of early parenthood, thank you for choosing us. We are learning and improving everyday. OZi Amit Sah Also if you’d like to join us on our journey: Apply here - https://binary.so/WgGth3v

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One of the most common patterns I see with founders is moving fast before the direction is clear. They jump straight to solutions. Features. Roadmaps. Shipping is good. It’s how you learn. But it works best when you’re clear on the bet you’re making. A founder I advise today didn’t come from product. So we focused on getting aligned on a few things before stepping on the gas: What do we believe is true? What signals do we have so far? What’s the fastest way to test it? We used small experiments. Clear hypotheses. Real user feedback. The goal wasn’t to slow down. It was to reduce wasted motion. Good products are rarely built by instinct alone. They’re built by fast teams who learn on purpose. If you’re building something new and want help pressure testing your direction, I’m happy to talk. The link to book is in the first comment.

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