Year 1 at a Startup

Looking back on my first year with a startup in year 1

Jacob Pitcher
4 min readJun 2, 2017

Startup.

Up until late 2015, the word didn’t mean much to me. Growing up in St. John’s, Newfoundland doesn’t really give anyone much exposure to the likes of companies sprouting up in Silicon Valley seemingly overnight.

Fast forward to 2017. I’ve had a year and a half in the trenches with HeyOrca (a startup focused on fostering better agency-client experiences through collaboration). Startup isn’t just a word describing some new company in “the Valley” with cool perks anymore. It’s a state of mind. It’s the ongoing pursuit of growth. It’s finding answers to questions you’re not even asking yet. And I’m loving it.

Here are a couple of things that have stood out to me about my first experience with a startup:

You don’t know what you don’t know — and that’s FINE!

The beauty of a startup is that it’s a blank canvas. Nobody has all the answers and nobody EXPECTS anyone to have all the answers. That’s half the fun!

This also makes for a sink or swim sort of environment. Can’t swim? You learn. And you learn some more. And then you go ahead and learn some more on top of that. Because that’s how you start and that’s how you grow.

A major contributor to my growth as a professional, and as an individual, was the “learning by committee” mindset in the early days of HeyOrca. Nobody has the answers or even knows all the right questions to ask, but somebody has to find them. Once somebody finds an answer, or a question that needs answering, it’s paramount to share that with the team.

What defines great teams isn’t just the ability to find all the answers, but choosing the right questions to ask in the first place.

Everyone is (or should be) appreciative of the fact that everyone else there is learning. You’re all in this together. You don’t know what you don’t know until you know it. And that’s fine.

Job Scope = Undefined

For a fairly long time after joining as Orca #4, there was no such thing as defined responsibilities at HeyOrca (even though the job posting I applied for said otherwise).

In phase 1 of a startup, the bottom line is to achieve growth — and growth is a shared responsibility.

What does that mean? It means forget about job titles and a list of predefined tasks. It means doing the next most important thing that needs to get done. Customer not happy? Make them happy. Big deal come into the funnel? Make the sale. Bugs in your app? Fix the bugs (or grab some coffee for whoever’s capable of fixing those bugs).

It’s chaotic. It’s messy. It’s stressful. And it’s a rush!

At this stage of a business, you get exposed to every conceivable function. You’re doing sales, you’re doing marketing, you’re doing customer success, and you’re building a product. The ability to dabble in, and learn skills in, all those different areas is invaluable.

High Highs and Low Lows

A startup environment is an absolute emotional rollercoaster.

If you join a startup early enough, it’s very difficult to not get personally invested in the successes and the failures of the team. That’s not a bad thing! It’s just a thing.

At HeyOrca, every small win was (and still is to this day) a big win. Progress is addictive. Growth is bliss.

When the bottom line of the business is so visible, and individual efforts visibly affect that bottom line, motivation comes easy. On the flip side, small failures can feel like big failures (and very easily turn into big failures) if you’re not careful.

You can almost feel the heartbeat of the company. Morale is critical and it can be volatile. The key is having a solid support mechanism for your teammates and righting the ship before it capsizes.

The Journey

The last thing that became really clear after my first year with HeyOrca has to do with the journey.

It’s not about the end goal. It’s not about hitting $1 Million in Annual Recurring Revenue. And it’s not about eventually getting acquired or going public (although that’d be super nice). It’s about how you got there.

When I think back on 2016, I spend very little time thinking about hitting our target and securing $2 Million in funding. I think about all the challenges we overcame to get there. I think about all the laughs, the smiles, the stress, and the obscene amount of information I stuffed in my brain. And finally, I think about all the great friends I made along the way.

The best part is that I’m lucky enough for the journey not to be over yet. I’m even luckier to be on that journey with the most amazing team.

Without HeyOrca, the word startup still wouldn’t mean all that much to me.

Thanks so much for reading! If you liked this story, feel free to show it some love by clicking the 👏 button or leaving a comment.

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Jacob Pitcher

Reader, thinker, dreamer | Jacob of all trades, master of none.