My journey from sales-led to product-led entrepreneurship
... and what I wish I had known before transitioning
I've spent years building companies, navigating the intricate dance of sales, fundraising, and building. My second venture, DataFleets, was born from grit, countless rejections (100 VCs said no!), and a relentless focus on closing deals, ultimately leading to a 9-figure acquisition. That journey was deeply rooted in a sales-led motion. We painted visions, showcased roadmaps, built relationships through compelling narratives and relentless hustle. And we built a ton of differentiated software too. Ultimately, it worked. But the truth is, even though we delivered software to our customers -- the product experience wasn't delightful. I wanted the challenge of creating something users truly love.
Now, I'm building Memex, the "Everything Builder for your Computer," inspired by Vannevar Bush's vision but aimed at augmenting human's ability to engineer systems, not just extend memory. With Memex, we're embracing a product-led growth (PLG) strategy.
The shift has been… humbling.
The Ego Check
One of the starkest transitions from sales-led to product-led entrepreneurship is the confrontation with your own ego.
In a sales-led world, especially early on, you are a significant part of the product. Your story, your conviction, the slick deck, the social proof – they can smooth over rough edges in the actual software. You're selling trust, a partnership, a roadmap. You can emphasize the groundbreaking tech (like the privacy-enhancing technologies we built at DataFleets) and the brilliant team behind it. Buyers are often signing up for a longer-term engagement, betting on your ability to deliver eventually. The more great names you have behind you, the more other great names want to join in.
Product-led? Forget it. Your pitch is the product. Right here, right now. Does it work? Does it solve the user's immediate pain? Does it deliver value today? Vision counts for maybe 1%. Social proof helps get a first look, but retention hinges purely on the utility derived.
If the product stumbles, if the UX is confusing, if it doesn't deliver on the core promise quickly, users churn. There's no smooth talk to save you. The product speaks for itself, brutally and honestly. It forces a level of humility, a stripping away of the founder ego, that sales-led motions can sometimes shield you from. You can't hide behind future promises; the present reality of the user experience is all that matters.
The Complicated Art of the Minimum Valuable Product
This leads directly to the second major shift: the ruthless focus on distilling value.
Sales-led allows, even encourages, showcasing a broad vision and an ambitious roadmap. You can sell the "platform," the grand architecture, the future integrations. Because the sales cycle is longer and the commitment deeper, the roadmap carries weight.
Product-led flips this entirely. Users are often evaluating multiple tools simultaneously with near-zero switching costs, especially in the AI-native tool space Memex occupies. They aren't signing a six-figure contract; they're trying your tool this afternoon.
This demands an almost fanatical obsession with the Minimum Viable Product (MVP) – or perhaps more accurately, the Minimum Valuable Product. What is the absolute smallest set of features that delivers a core piece of value, elegantly and immediately? How quickly can we ship that as fast as possible?
At Memex, we're helping users learn and build 10x faster. Developers, researchers, product managers, analysts, entrepreneurs – people who need to get stuff done and are only interested in a tool if it truly amplifies their productivity. They don't care about our five-year plan; they care if Memex can help them create that custom OCR workflow for their research project today, build that internal tool tomorrow, or finally get that side-project idea off the ground this weekend.
This forces incredibly stringent prioritization. You have to say "no" constantly, not just to bad ideas, but to good ideas that don't serve the immediate core value proposition. It's about depth and polish in a narrow scope, rather than breadth and ambition. It requires intense focus and a willingness to kill your darlings if they distract from the core user journey to value.
Great products are built on relationships: whether sales-led or product-led
Going into Memex, I carried a common misconception: "Sales-led is relationship-driven, but product-led is more about the numbers... funnel optimization, conversion rates, analytics."
I couldn't have been more wrong.
Yes, analytics are crucial. You live and die by activation rates, retention cohorts, and feature adoption metrics. But the foundation of a great product, especially an early-stage one navigating the messy path to product-market fit, is built on relationships. Just a different kind.
Instead of wining and dining prospects, you're deeply engaged with your user community. They aren't just data points in your funnel; they are your co-builders, your sharpest critics, your most valuable source of insight.
The key to a product-led strategy is a great product. And you can't do that without having great users that partner with you early on to help you fix the bugs, improve the UX, and prioritize the features that drive true value. Those partners ultimately become close knit relationships.
This quote, which I shared recently, captures my perspective. Building Memex has reinforced this daily. Our early users aren't passive consumers. They are active participants. They report bugs with precision, suggest UX improvements with passion, and champion the features that genuinely solve their problems. These interactions forge deep, collaborative relationships built on mutual respect and a shared goal: making the product better. The work is hard, but when our users recognize the effort, it means the world to us.
The Long Game
This transition isn't easy. It requires a different mindset, a different operating rhythm, and a constant check on the ego. But building Memex this way feels right. Minutes spent debugging issues for a user or deciphering their pain points to improve the product feel much more productive than the time spent perfecting a pitch deck to close a single account. It forces a clarity of purpose and a relentless focus on user value that is both challenging and deeply rewarding.
The journey from sales-led to product-led is less a change in destination and more a change in the vehicle and the terrain. The goal remains the same – building something impactful – but the path demands a different kind of resilience, humility, and a deep, abiding focus on the product as the ultimate expression of the vision. And perhaps surprisingly, it deepens, rather than diminishes, the human connection at the heart of building something new.