
What you learn working with 1,000-person companies
Yesterday I had a Google Meet conversation with somebody who asked me, “Have you ever worked at a startup before?” and the involuntary laughter burst out of me like a xenomorph as I confirmed, “Yes!”
Over my career, I’ve been employee #6, employee #50, employee #250. I’ve worked almost exclusively with startups, one seat on the rocket ship after another.
Once I made the mistake of working on a project for free under the promise of equity, just to get ghosted by the charismatic founder who went on to exploit even more unassuming builders before striking undeniable, celebrated success with his next idea.
I’ve also been a failed founder, somebody who sold a vision and got people together around a mission just to drop the ball. I couldn’t figure out how to make the money work.
What I haven’t done yet is work on anything like a FAANG.
Until recently, I had never worked with any post-IPO company with more than 1,000 employees. Not unless you count the couple of months when I was still at Pardot after the ExactTarget / Salesforce acquisitions.
Even in college, none of my jobs or internships were big corporate. I worked at small PR companies and independent newspapers. I slung coffee at the local chain—not the drive-thru behemoth where making a latte was reduced to pushing a single button.
As I’m working inside a huge publicly traded company for the first time, I’m surprised at what’s the same and what’s different.
The Big Company experience is a challenge. I’m grateful for the detour into this unfamiliar territory because I’m learning a ton that will change the way I approach work in the future.
A few observations so far…
What’s different at big companies
Deadlines are real
In a small startup, there are fewer events with truly hard deadlines that cannot be moved. Maybe an engineer thought they could knock out their intern project in a quarter but it takes them a full year to build. Maybe you need more time to edit a video promo, so you call an audible and push the marketing launch out a week.
It’s not great and you lose trust every time you get the timeline wrong, but the scope of people affected is relatively small and it’s usually possible to recover.
In the 1,000-person company, it’s the opposite. Most tasks—big and small—have hard deadlines that cannot move. Because there’s always somebody waiting on your work to pick it up and run the next leg of the race. If you miss that one hour window when they’re free to receive the baton, the whole relay falls apart.
Estimating tasks, checking out-of-office schedules, and communicating handoffs in advance takes a lot of work but it’s the bulk of the job. Everybody has to be an excellent project manager in addition to whatever skill area they own. Which brings me to…
Snap lines matter
Who’s got the ball? When you’re in a tiny startup, everybody wears multiple hats and job responsibilities can be pretty fluid. Bias toward action is rewarded, and it’s better to move fast than to worry about stepping on toes.
In a big company, roles are extremely specialized and it’s not cool to overreach. Before you take any action, you need to stop. Pause. Look around and check whether somebody else is responsible for doing the job. In a lot of cases, even if you could hypothetically knock out a task yourself, you might not have the role-based access control to DIY, so learning to ask for help and depend on others is key.
Internal artifacts are products
As much as I personally love tools and internal documentation, the reality is a lot of internal artifacts like product messaging architecture, journey maps, playbooks, and brand guidelines become digital clutter inside a startup organization. Or, processes change so quickly your docs get stale overnight and it’s nonsensical to devote too many hours to cleaning them up. As a best practice, it’s generally better to ship something customer-facing than to maintain the internal reference material.
In a big company, the internal artifacts you create actually get used. They’re like products you need to maintain where your co-workers are the end-users. It’s weird to run what’s essentially an internal marketing launch for a spreadsheet…but it’s super cool to watch how those tools enable people to do great work. I can imagine how these artifacts save people from needing to send a 1:1 DM or go down a rabbit hole to get unblocked.
What’s the same
Between startups and big companies, these things are mostly true:
- The companies that put customers first will win
- Change is constant
- You can never have too much alignment
- Be kind—people are quietly carrying grief
- Shared values hold teams together when stakes are high, and
- People will get annoyed if you make too much noise in Slack
Every startup dreams of being a big company when it grows up. Even if you build to exit early, it’s likely you’ll work in the bigger enterprise for a bit before you can bail out and start back at square one.
What matters isn’t the size of the org but the scale of your impact.
It’s always fun to work on big things.