My Journey From A Fortune Five Giant To A Startup, One Year Later

A year ago this week, I left my job at Microsoft, currently one of the five largest companies by market capitalization, to join a start up, Ampush. Lots of people decide to leave big companies for small ones. For some, it doesn’t work out, as Dan Lyons describes of his “hellish” experience at HubSpot.

Sandi MacPherson, editor-in-chief of Quibb, asked me to comment on Lyons’ story. My response: it appears as if he and HubSpot were a cultural mismatch. He writes condescendingly about the company’s “change the world” mentality, efforts to inject youthful fun into the workplace, and its unshakeable belief in the power of inbound marketing.

Having navigated my own transition from one of the world’s biggest companies to a much smaller and younger one, I can’t think of any factor more important to making it work than cultural alignment.

While I don’t claim to have figured it all out, here are some of things that were different – and a few that weren’t so different – about going to work for a startup, compared to being at a big company. Not all are unique to Ampush, though all of them are the sorts of things a job seeker should consider carefully before making the leap.

Millennial co-workers

I had to learn how to connect with and manage young Millennials, who represent a majority of our workforce. Though the generation is unique, getting to know them does not require a manual. If you want to relate to them (or anyone else), you have to come to understand where they come from, what motivates them, and what’s going on in their lives outside of work. Just ask the right questions and learn to respect your differences.

Someone more than 10 years my junior manages me, and that also represents a first in my career. This person doesn’t have as many years of experience as I do, but the types of experiences he does have are very different. That means we have a lot to learn from one another, and that has laid the foundation for a productive relationship.

Longer hours

I’m out the door by 7:35a most mornings and arrive earlier than most of my younger teammates. To get home before 8p, I leave the office at 6:30p; most others check out later than that. It took me some time to get over the uneasy feeling that I wasn’t among the last to leave, even though I’m now on and available for 12+ hours every day.

Once or twice a month, Ampush holds office dinners or happy hours that I stick around for. I get home 90 minutes or so later than usual on those nights, which means missing time with my wife and daughters, but nothing has helped me get to know my colleagues more. My wife and I talked about these intrusions into our home life before I accepted the job. That helped avert any unpleasant conversations after I started.

Company candor

One of Ampush’s values is “Tell it like it is – nicely.” I see it as a manifestation of the company’s Midwestern DNA. This has required one of the bigger adjustments on my part. At my larger former employers, I was much more mindful of controlling the message. That doesn’t fly at Ampush. We’re far from perfect, but for the most part, people feel more comfortable asking tough questions and getting and giving feedback.

Techy perks

The company subsidizes our lunches. It provides bagels and cream cheese and in-office catering once a week. We have a ping pong table, video game consoles, a pantry stocked with snacks, and even a kegerator. They help keep energy levels up. I’ve never seen anyone abuse these perks. I’m grateful that I don’t have to spend as much of my own money on food.

Some parts about being at a startup have felt very familiar. At Nokia, I had to learn to work with less and less each year as we cut back on expenses. That led to occasional long hours and finding inexpensive resources to help me complete projects. I came to expect fluidity in my role. All these things helped prepare me for life at a startup.

My advice to anyone considering a startup is to look beyond how well your resume matches the job description. Ask the company about things it does to build and grow its culture, then see if you can attend one of them.

Learn what the company is like in these moments and you’ll figure out whether you can see yourself fitting in.