Here’s Why You Should NOT Work at a Small Company / Startup.

Posted on the 22 September 2015 by Rwilner


I recently wrote about why you should work at a very small company.  Now I’m going to write about why you shouldn’t.


Everyone wants to work at a startup or a very small company, Or everyone thinks or feels they should want to.


Working at a tiny company can be rewarding.  Life changing. It can allow you to impact the lives of millions.

Guess what?

1) Those things are not guaranteed.  In fact, its almost a guarantee that none of them will happen.

2) You can absolutely make those same things happen at a medium or big company, or any company.

So…if you’re embarrassed because:

  • You’re working at a small company but (secretly) want to leave it for a bigger one or
  • you think you want to work at a small company because that is what you think you’re supposed to want, or
  • you don’t want to work at a small company but you’re e!embarrassed to tell people that…

why? Why are you embarrassed?

You shouldn’t be. Here’s a story from my experience to prove it.


I got a new job at a big company. I would be doing at a global level what I had been doing previously at a local level. (This also known as a promotion)

The job was to manage the global portfolio of projects.

What does manage mean? I’m not sure, but here are some other words that mean the same thing, in this context: understand, measure, communicate, characterize, analyze.

Actually, that sums it up: my new job was to measure, characterize, understand, analyze, and communicate the global portfolio of projects.

My new job was to answer this question: we are investing many millions in projects. What are we doing? How are we doing?

I thought, surely at this big company, there are robust and established things to do this. I will inherit a system, processes, tools, etc…and administer them. Improve them. Refine them.

When I actually started the job, I discovered something. This thing I discovered has been discovered by countless people before me.

None of that stuff was in place. I was starting from the ground.


Because this complex, profitable, effective company I was fortunate to be a part of… It wasn’t built to do “portfolio management.” It was built to make things and ship them. (And it was pretty good at that)

So I had to build it. Actually, first I had to define “it” in the first place. What is “it”?

And I didn’t have a big staff, or a budget, or a manual to tell me how.

I just had to make it happen. And I had to do it fast.

Boy. Sure sounds like a startup, doesn’t it?


My boss gave me the autonomy and freedom to develop my path forward and execute it. She trusted me to deliver. That’s why she hired me.

So I decided to approach my job like a startup. Or at least, like I was starting something up.

But there was one major difference between what I was doing and what I would be doing at a startup: I had the support and resources of an at-scale business. And that support gave me the ability to build and launch in ways that would have been otherwise impossible, or at least, much, much harder.

Here’s what we accomplished in about 9 months:

We built a network of like-minded colleagues. Suddenly…instantly…I had a team.  My team was not there because I was paying their salaries.  They were there because they wanted to help define the mission and vision for this new thing. And they committed to help realize it.

We developed and deployed standards. Sounds trivial. But capturing and reporting data on hundreds of projects across multiple locations, geographies, and sub-cultures is hard. A standard was the best (only?) way to understand what’s going on.

We developed out first quantifiable performance measures. These are also known as KPIs or metrics. This is so important.  Why?  Because it let us figure out where we, as a team of like minded individuals, needed to focus to improve our work.

Think about it this way: with our measurement framework, we were no longer carpenters fixing desks to make them sturdier, or more functional. We became carpenters that were learning to become better carpenters, so that every desk we make will be better, forever.

We built the first customized reporting package for the business. This is not some generic consultant’s reporting package based on “generic large businesses like you best practice magic quadrant tribal knowledge buzzword!”.


We built the reporting package using lean startup techniques…shipping our reports, iterating, and shipping again. And once enough people saw them…

We built a platform where executives reviewed these reports, every month.

So to recap:

When we started: goose egg.

9 months later: data-driven custom reports based on a global data standard, reviewed monthly by executives, driven by a team of like-minded professionals, with a plan to constantly improve the process, data, reports, and ultimately impact the business and worldwide customer base.  We were solving problems.

Would you be excited for the next 9 months?


Big companies have massive liabilities. We all know about them. We complain about them to our friends, spouses, co workers. They’re documented and studied in business schools. There is an entire consulting industry built to (alledgely) fix them.

What about big companies’ assets? No one talks about those.

I will. Here are a few. (Are there more?)

  1. Instant access to a customer base. Startups are about building a customer base. Large companies have that already. So instead of building it, you can go straight to delivering to it. (Or build a second, or third one, I’d you want)
  2. Instant access to many types of customers. Internal. External. Vendors. Contractors. Consumers. Executives. Pick who you want and make what they need.
  3. Resources. This one is obvious.  Money, people, time. Build your business case and get what you need to do what the business needs.
  4. Opportunity. A big company needs lots of different functions to achieve its business strategy. Sales, marketing, research, manufacturing.  Dozens, maybe hundreds more. Work in all of them. Or work in one for a really long time and learn to dominate it. Just had kids? Take something low key. No kids yet? Travel 25 weeks a year.
  5. Opportunity part 2. So many problems! Every problem is an opportunity. Every fix ultimately impacts your global customer base. Pick the one you want to fix. Build your business case and go fix it. Then pick the next one. Then the next one. This is fun!
  6. Mentors. Big companies have awesome people in them. 10k people in your company? 100 of them are geniuses. That’s just statistics. Do you know who they are? Find them and work for them, work with them, work near them, around them.  Remember: you are the average of the 5 people you spend the most time with.
  7. Skills. Ideas take hold through leadership. Leadership happens through influence, not reporting structure. Large organizations are an ideal place to develop and use this ability to…again…deliver for a global customer base.

That’s 7. Can you think of any more?


A final thought: what is a theme in the things I identified above?

Customer base.

When you choose the company to work for, what you’re really choosing is a customer base. (This is true even at a startup, but the difference is a startup has a potential customer base, whereas a big company has ACTUAL CUSTOMERS)

Are you curing a disease? Transforming a consumer experience? Delivering a new technology to the world?  Are you passionate about your customer base? 

After you choose your company, you need to choose what to do. Can you link what you’re doing to your company’s strategy? To the customer base?

One thing is true: it’s human nature to want instant gratification. (It is mine, for sure)

I don’t want to wait for the customers. I want to make it better for customers, and I want to do it now.

I can do that at a big company. You can too.


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