I run a 1,000-person company, but it's not all that different from my first day as CEO — when I gave myself a title, rolled out of bed, and got to work

Ryan Holmes; Business InsiderRyan Holmes, CEO of Hootsuite.
  • Being CEO for a company of one and a CEO for a company with many employees requires similar skills.
  • Ryan Holmes, founder and CEO of Hootsuite, started a company called Invoke in 2000.
  • His first day he probably rolled out of bed and started building web tools. After a few months, he hired a few employees.
  • From Invoke, he branched out and created Hootsuite, which has since grown into a global company.
  • He says knowing how to be a jack of all trades and a master of some is crucial to leading a company, no matter the size. It’s also important to hire people smarter than you, and prioritise culture.

The great thing about the CEO title is that you can give it to yourself. At least, that’s what I did.

Back in 2000, the tech bubble had just burst and I was out of a job. So I founded my own web agency out of my apartment, consisting of one employee – me – called Invoke, and appointed myself CEO.

To be honest, I don’t remember my first day at Invoke very well. I probably rolled out of bed, turned on my computer and started building web tools. After a few months, there was enough work to hire my first employee. After several years, Invoke had 20-plus team members and we were doing everything from building tools to handle video campaigns to managing social media on clients’ behalf.

And thenHootsuiteentered the picture.

Logging in and out of different clients’ social networks was a headache, so my team created a tool to monitor multiple accounts on one dashboard. We quickly realised that lots of other businesses needed a tool like this, too. So in 2009, I made the decision to spin out Hootsuite as a separate company.

This time around, my first day as CEO was a bit more nerve wracking. On the outside, not a lot had changed. I was actually in the same office – we just tore down a wall to make some more room – and I’d taken seven employees with me from the original company, so there weren’t any unfamiliar faces.

But in another respect, I’d left all I’d built at Invoke behind, under the management of my partners. In addition, for the first time, I’d decided to secure financing. So I had investors and employees to think about, despite having no revenue coming in. The project had considerably higher upside, and considerably higher risk.

That first week was a whirlwind. There were lots of late nights and endless fires to put out. This was compounded by a back injury at the time which left me walking with a cane for a year. I had cobbled together a DIY stand-up desk from cardboard boxes and managed to soldier through with a lot anti-inflammitories.

Luckily, the employees around me were all self-starters. Everyone threw themselves into finding a way forward – even when that meant going beyond their usual job description. I think it’s critical to the success of any startup to have these kind of folks early on – adaptable, ego-less, and with no pretension or attitude.

Fast forward to today, and I’m now the CEO of a company of around 1,000 people. In some respects, everything has changed from the days of running a business out of my apartment. We now have more than a dozen offices around the world.

But I think it’s important to emphasise thatnot everythinghas changed. In fact, many of the skills I learned as the CEO of a company of one still serve me as CEO of a global company with more than 16 million users.

I had to gain basic competency in many areas, or the company would have died on the vine

The most critical lesson that I carry with me is the importance of being a jack of all trades and master of some.

As the CEO of a tiny company, this is a matter of necessity. To get off the ground, I had to learn – largely on the fly – about nearly every facet of running a business: product and engineering, sales and marketing, accounting and finance, customer service and client relations, human resources and more. The process of building a business, from the ground up, truly represented a mini MBA for me.

I’m not saying I was an expert coder or sales guru. But I learned enough to be dangerous. I understood enough product development to vet the developers I was hiring. I had learned enough about sales to hop on calls with key customers and drive a deal home. I learned how to make a compelling pitch to investors. Really, I had no choice. Either I gained a basic competency in these areas or the company died on the vine.

Hire people who can do the job better than you can

Eventually, though, I also learned an equally important lesson. As you move beyond the early startup stages, the quickest (really, the only) way to accelerate growth is to aggressively delegate and not try to do everything yourself. As soon as you’re able, in other words, hire people who can do specific jobs better than you can. Hootsuite had just a fledgling sales team, for instance, when I brought our first chief revenue officer into the picture. With plenty of past experience scaling global teams at major companies, he quickly grew our sales org and set us on course to target huge businesses.

These oppositional skills – knowing enough to be dangerousbutknowing when to delegate – continue to serve me as a leader today. The blend of general competence and humility isn’t always easy to get right. But, looking back, being CEO of a one-person company can be great training – whatever size company awaits you down the road.

Looking back, right from that first week, I think we managed to get a few things right that really helped in the long run as Hootsuite grew to dozens, and then hundreds of employees. One of the most important of was also our prioritisation of culture. We may have been small, but we took the time to go for a bike ride at lunch or share a barbecue on our rooftop after work.

In hindsight, that stuff isn’t fluff – it’s what makes a job something that people can believe in and get behind.

Ryan Holmes is the founder and CEO of Hootsuite. Follow him on Medium or Twitter.

NOW WATCH: Ideas videos

Business Insider Emails & Alerts

Site highlights each day to your inbox.

Follow Business Insider Australia on Facebook, Twitter, LinkedIn, and Instagram.