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February 13, 2018


How to grow from a 5 person company to a 500 person company.

“Once you build out your executive team you’ll have so much time on your hands you won’t know what to do with yourself!” said one of our investors. We’d just raised our $20M series B for Bigcommerce in 2012 and upon hearing that, both Eddie and I thought “Ha, yeah right! I don’t have time to do anything but work and that won’t change!”.

Back then our “executive team” was me, Eddie and Rob — our current CFO and COO. We were a force to be reckoned with, but we were just 3 people.
Between 2012 and 2014 we worked hard to build a great leadership team at Bigcommerce. We agreed on the positions we wanted to fill first — starting with the roles that would help us continue our growth. Engineering was first. Then product, sales, support, marketing, business development, communications and most recently, corporate development.

We worked with some great executive search firms, leveraged our network (specifically via our investors including Larry Bohn, Steve Case, Kal Raman and Lorrie Norrington, the former president of eBay International), ramped up our PR, doubled-down on our company culture and started to win a lot of the “best places to work” awards.

The buzz we were able to create no-doubt helped in our recruiting efforts, considering just a few years earlier there were 12 of us working out of a small office in Sydney, Australia. If you lived in San Francisco in 2014 I’m sure you remember our #GetPoached campaign.

It was ballsy, but wow did it work.

From 2012–2014 we built a great leadership team with amazingly talented people from companies like Google, Salesforce, Paypal and Twitter (hi guys+gals if you’re reading!). There were a few bumps along the way, but as each executive started to ramp and really own their strategy, we felt comfortable handing off the important decisions.

I remember hearing Jack Dorsey’s now-famous quote that great CEOs are “editors”, not “writers”. And if you start to “write” more than you “edit”, you’ve hired the wrong person.

Your job as an executive is to edit, not write. It’s OK to write once in a while but if you do it often there’s a fundamental problem with the team. Every time you do something ask if you’re writing or editing and get in the mode of editing.

Simple translation — if you start to do the work of your executive team, you’ve hired the wrong people. They should share their decisions and strategy with you, but you shouldn’t be creating it for them.

As we started to “hand over” the reigns to our new executives, I kept hearing that quote about being less busy in my head. And funnily enough, our investor was right. As you scale your company and hire people who are much smarter than you, it’s scary at first but eventually, it becomes liberating. You definitely spend less time “in” the business and start to work more “on” the business, which means a lot more time on strategy and helping to reel in the “big fish” for important roles, key partners, etc.

You’re still amazingly busy but in a very different kind of way.

When I stepped away from Bigcommerce early last year to build my new performance management platform, PeopleSpark (check it out if you’re a CEO and want to create a great culture), I spent some time reflecting on the 6 years I spent at the company and finally understood what our investor meant when he said we’d be less busy.

Good CEOs are busy working “in” the business for the first few years. That’s just how it is. You wear 7 different hats. One day you’re answering a support ticket, the next day you’re interviewing a VP of Marketing. I’m back in that position now at PeopleSpark and it’s exciting, but the almost-hourly context switching is very different than being the CEO of a 500-person company.

As you start to grow from a tiny startup into something that resembles a more mature company, your #1 priority becomes surrounding yourself with incredible leaders who can do their jobs better than you ever did.

You start to nod in agreement more, trust your team and think to yourself “wow, this is one hell of a team we’ve been able to build!”. You delegate more, question less and start to see the big picture.

And that’s how you become less busy working “in” the business. But you'll always be working “on” the business. That’s why you’re the CEO.

Are you a leader at a fast-growing company? One of the best ways to spend less time “in” the business and more time working “on” it is to give your employees a way to regularly tell you what’s going well, what’s not and how to improve. PeopleSpark can help. Try it free for 30 days. You’ll love it.

This article originally appearedhere. Follow@mitchellharper for more articles like this.”. Featured image via Flickr.

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