I've worked in both environments, close enough together that the contrast is still sharp. The skills that made me effective in one context actively hurt me in the other, and it took longer than I'd like to admit to figure out why.
The surface difference is obvious: startups have fewer stakeholders, faster feedback loops, less process. Enterprise has more stakeholders, slower decisions, more documentation. But that framing misses what actually makes each environment hard.
3 decision-makers. CEO uses the product on Wednesday, you're redesigning it by Thursday. Speed is the advantage and the trap.
Payments, logistics, and merchant platform teams all have different release cycles, technical constraints, and definitions of done. Alignment is the actual work.
What makes startups hard
At a startup, the real challenge isn't the speed - it's that the decision-making authority is concentrated and informal. Three people can move the roadmap, and two of them are in the same room as you. That sounds great until you realize it means you're constantly managing founder intuition against user data, and founder intuition often wins.
The feedback loop is fast but noisy. You ship something on Tuesday, the CEO uses it on Wednesday, and by Thursday you're having a conversation about why the button is in the wrong place. That's useful signal sometimes. Other times it's one person's preference dressed up as product direction. Learning to tell the difference is most of the job.
The technical decisions also move fast in ways that create debt. At a startup I worked at before Uzum, we made an architectural choice to store user preferences in a single JSON column because it was fast to implement. Six months later, when we needed to query across those preferences for a segmentation feature, we were doing full table scans on a 2 million row table because you can't index inside a JSON blob efficiently. The PM who pushed for speed over structure (me, in that case) didn't fully understand what that choice would cost later. At a startup, you often don't have time to understand - you just move.
What makes enterprise hard
Enterprise isn't slow because people are incompetent. It's slow because coordinating large numbers of people with different incentives and different information is genuinely hard, and the process overhead exists to manage that coordination.
At Uzum, a decision that touches payments, logistics, and the merchant platform involves teams with different technical constraints, different release cycles, and different definitions of "done." The payments team deploys with a full regression suite and a 48-hour soak period because a bug in payment processing at our scale means real money lost for real people. The logistics team has different constraints. Getting these teams aligned on a shared feature isn't bureaucracy for its own sake - it's the actual work of building something that works across a distributed system.
The mistake I see PMs from startup backgrounds make is reading the slower pace as dysfunction and trying to work around it. They make decisions in hallway conversations and tell people later. They ship things without proper alignment and then wonder why the other team's service broke. In a microservices architecture, you can't just ship a change to your service without understanding what downstream services depend on your API contract. The "move fast" instinct that worked at a startup will cause production incidents at enterprise scale.
The reverse failure is also real. Enterprise PMs who move to startups want sign-off before every decision. They want a framework for everything. They write detailed specs for features that will change three times before they ship. The startup doesn't have time for that, and the founders will lose patience fast.
What actually transfers
The core skill is the same in both contexts: understand what people actually want, not just what they're asking for.
A founder saying "we need to move faster" is usually saying "I'm scared we're going to miss the market window." A VP of engineering saying "we need to refactor this service before we add features" is usually saying "the current architecture has a bottleneck that will cause incidents at 10x our current load, and I need you to understand that before you commit to a roadmap." A head of sales saying "we need this feature for a deal" is usually saying "I'm being measured on this quarter's numbers and I need help."
When you engage with the underlying concern instead of the surface request, the conversation changes. This is true whether you're in a 20-person startup or a 2,000-person company.
What doesn't transfer is the playbook. The tactics that work in a startup - moving fast, making decisions informally, shipping and iterating - can get you in serious trouble in enterprise. You need documentation. You need alignment. You need to bring people along, not just move and tell them later. Not because enterprise is bureaucratic for its own sake, but because the cost of misalignment at scale is much higher than the cost of the extra meeting.
Reading the environment
The best PMs I've worked with can read the environment and adjust. They know when to push and when to wait, when to document and when to just decide, when the process is serving coordination and when it's just friction.
That's harder than it sounds because it requires you to be honest about which situation you're actually in. It's easy to tell yourself the process is dysfunction when really you just don't want to do the alignment work. It's also easy to tell yourself you need more process when really you're just uncomfortable with ambiguity.
The tell is usually the outcome. If your decisions keep getting reversed because you didn't bring the right people along, you need more process. If your team keeps missing windows because decisions take too long, you need less. The environment tells you what it needs - you just have to be willing to hear it.