I’m on a forum run by one of our investors here at Gauntlet and someone recently asked a question I have thought a lot about:

How is being a Product Manager at a large company different from being a PM at a start-up?

I have worked at both a large companies (MSFT, Goldman Sachs) and small start-ups (when I joined Gigster I was the 9th employee and at Gauntlet was the 1st). Everyone should do both.

Big companies

Being a PM at a larger company is great in many ways. I think the main benefits are scale, support, and security.


I was the PM for a pretty obscure API in Windows and it had thousands of developers use it within the first few months of launch. Even if you are building the main API at an enterprise SaaS start-up, it might only have that sort of usage after years of development and sales. In general, working at large companies allows you to work on small things that leverage the scale of your large company to have an outsize impact. I remember talking to a PM for Excel who mentioned that one button she had added to the product created something like 5 million man-hours of user productivity because it was a button that got pressed a billion times a year.


When you PM at a large company, you can dedicate almost all of your time to core PM things like data analysis, roadmap planning, writing specs, working with user research etc. You have an army of people that help you focus. When I wanted to do a user research study at Microsoft, it was one 15-min meeting showing the researcher the feature and then a month later I walked into a purpose-built room with a one-sided mirror and watched as the user research team ran through the product with a group of people they had hand-selected to match Windows usage demographics. At a start-up, you are doing all of this yourself, and you aren’t doing nearly as good of a job. Do you want to grow the impact you have at a larger company? There is probably a novel’s worth of documentation on how to do this, a company-wide mentor program to connect you with people that can help, and your manager is probably dedicating 80% of her time on management. At a start-up, the opposite is often the case - maybe no one knows what you’d have to do to get promoted to Head of Product or Senior because it’s possible no one has done that yet. You might have to push management to define these things before you will be able to accomplish them, and your manager (the person who is supposed to help) is probably spending 80% of her time on her IC responsibilities and doesn’t have the time to help you figure this out.


Both job security and financial security are going to be better at a large company than a start-up. At start-ups, there is always a chance that the start-up will fail, pivot, or otherwise change in a way where your job is not longer extant or necessary. Cash compensation at large companies tends to be higher by quite a large margin than at start-ups as well. If you are starting a family, have a mortgage payment, or are otherwise unable to trade cash compensation for illiquid equity compensation (as you are asked to do at almost all start-ups), making the start-up life work can be quite a strain.


With that said, you might think that I am probably a MSFT lifer who has somehow grifted their way into this forum. However, I have worked at start-ups for the past 4 years and have no plans to work at a large company again in the near future. I strongly prefer working at start-ups to larger companies. I prefer working at start-ups because I think they are better for scope, opportunity, and motivation.


When you are the PM at a start-up (or even just one of a few PMs) you should have a considerable impact on everything from the overall direction of the company to the types of drinks in the fridge. If there is anything you don’t like, you can change it. If you find a process that works on your team, you can try to roll it out across the company. Also, even a relatively junior PM might be the sole owner of a product or large feature set. In general, at a smaller company you have so much more impact on the things you work on than at a large company. Now, those things impact a smaller number of people, but this can be a good way to get a lot done, bringing me to my next point.


Start-ups provide a tremendous opportunity for the people who work at them. When your start-up is growing really quickly, it is nigh impossible not to become a manager within a year or two. You also have the opportunity to bring something from zero to one, in Theil-speak. You get to build a new product and develop it into a successful one. This is just a better opportunity to put something on your resume that is truly impressive than you would get at a large company. Sure, at a large company you might be able to make a change that drives $2mm in incremental revenue (on a product with likely billions in total revenue). But what would make someone in the future want to hire you more? Doing that, or starting a product that had $1mm in revenue? There are better opportunities at start-ups to do something that shows to future employers how valuable you can be. Also, in the case that your company ever finds an exit, then you have the opportunity to make quite a bit more money than you would have at a large company.


I do my best work when I am motivated, just like most people. I feel more motivated at start-ups because everything you do matters, you have broader responsibility, and nothing can stop you from getting stuff done.

Everything you do matters

As the PM at a start-up, you are building products. Your performance is likely tied to revenue, something inherently valuable. If you fail, the company might fail. Some people might find that stressful, I find it motivating.


I mentioned a friend above at MSFT with her million man-hour button. Imagine you are that friend and your entire task for this month is to just spec a button. You schedule meetings with partner teams, get estimates from dev, etc. - but just for one button. I don’t find this particularly motivating - you are not doing anything valuable per se. Even if I was the best button-PM in the world, I still wouldn’t really know anything about building products, though I would know a ton about building buttons. The amount of specialization that you have to do is something I find inherently demotivating (to be clear - this gets much better as your career progresses). This matters a lot to me - as an entrepreneurial person who has considered founding a company, it’s hard to see being a PM at a large company as a path to doing so. At a start-up, it’s easy. If you are reading this and think that my reductive take on this button PM sounds a bit ego-driven, you might be right!

Getting things done

At a start-up you can move mountains to get stuff done. Imagine you want to release a new product that could really sell well, but your Customer Success team can’t make the changes to support this product, at least for a long time. At a very large company, that might doom your goal of releasing the product in six months let alone ever. At a start-up, processes and responsibilities are so much more flexible, you could conceivably still release quickly - smaller groups inherently can organize around value quicker. Anything you don’t like or you think could be improved, you can change.

There’s value in both

I emphasize above that everyone should work at both a small and a large company. I am extremely glad that I worked at a large company before working at a start-up. I just came in with so much knowledge of how things could be done - it was easy to make progress when faced with ambiguous paths forward since there was always a path to fall back on. Now, you won’t be able to apply your big company playbook at a start-up mindlessly - you will have a bad time - but it is a good place to start. Also, by working at both, I now have a pretty good idea of what works best for me.

One final caveat regarding start-ups - if your start-up is not going well, it can be extremely difficult to realize any of the advantages I mention here. Not surprisingly, start-ups carry quite a bit of risk. I don’t think the expected return on working at a start-up is higher than at a large company, all other things being equal. In fact I think the expected value at a large company is probably slightly higher. However for me, as someone who is risk tolerant, entrepreneurial, and inherently more motivated by 0-1 opportunities than 1-10 opportunities, start-ups are the right choice. You need to work at both to know what the right choice is for you.