Ryan Holmes of HootSuite on How to Recruit, Retain, and Manage a Growing Startup Team

In launching matchFWD, a social recruiting platform that connects job creators and job seekers, and gives connectors something to do, our goal is to use social media to help professionals find the right fit in the most enjoyable and rewarding way.

In light of HootSuite’s success, I ask Ryan Holmes, CEO of HootSuite and founder of Invoke Digital Agency, on his vision in hiring and keeping team players.

PHIL: How is HootSuite doing?

RYAN: Last year was busy. We’ve experienced crazy growth going from 25 employees to more than 100, from zero revenue to a $10 million run rate, and to a usage of sending 150 million messages per day.

This year we want to increase our product on a number of fronts. We launched our developer App Directory, which helps developers build applications for HootSuite. We’ve had good uptake with 26 apps now added and many more in the works.

We want to build team functionalities so we can help coordinate social business as people are looking to get more of the rest of their team into the social, more than just the marketing team. Social touches every department in the organization so we’re helping give tools that help the organization lead more effective teams throughout the whole enterprise.

PHIL: What makes you stand out from other employers?

RYAN: We’ve had a blessing of having a fun, exciting story. Amazing talent has come our way on all fronts: engineering, sales, and marketing. The key to our success has been to attract great talent.

We are on track this year to go from 100 employees to 250. We market on social media when we are at a hiring fair. We realize how critical social media has been to our success. For many people on the team, they are getting an opportunity to work on a product that is shaping how people communicate and revolutionizing social communications. They are able to see behind the scenes in a way that not many people could in their career.

In our engineering team, we have over 60 Amazon EC2 instances running and scaling in real time. From an engineering perspective, this is a very interesting problem. The experience that our team is getting in working on that is invaluable. There are very few companies on the planet that are doing something like this.

We look at doing things in a revolutionary way in human resources, sales, and marketing.


Ryan celebrates cracking number one on the Techvibes Startup Index in 2011.


PHIL: When your team grows, what do you find is the most important thing to manage?

RYAN: When you’re a seven-person team, it’s easy to instinctively reach across the table and know what each person is working on. With a 20-, 50-, 100-person organization, the challenges increase. We are trying to anticipate issues in order to be in a good position to deal with them.

At 70 people, we realized that communication is going to become a bigger and bigger issue so we started organizing town halls to talk with the team about where we’re at, what successes we’ve seen, and where we’re going. This helped a lot in aligning us on where our product is going and where our sales strategy is headed.

It’s funny, as we welcomed our 100th employee, a lot of people were asking for our values, mission statement, core principles, and this was an exercise that I hadn’t sat down and done because I assumed that everybody just gets it. As your organization gets bigger, people don’t just “get it” because they are walking into a living, breathing thing and it takes a while to feel what the culture feels like.

The more aligned you can get people throughout the whole process the more efficient you will be.

PHIL: I am guessing you are very involved in hiring.

RYAN: My human resources person sits right across from me and we speak daily on new hires coming in. As a startup CEO, you have to be involved in all aspects of the business, ensuring that the right organizational structure is in place, and helping your management team execute on this structure.

I always try to create roles around people and their skill set. I’ll often re-write roles to fit a person rather than hire a person who is not suitable or passionate for a role. I’ve had certain people come back four times to interview for different roles because we love the person so much and think they’re great for our culture, but we didn’t have at that time a role for them. We ultimately found and created one for them because we wanted to have them working with us.

You sometimes have to wait for a while until you find the right person. When you do, you feel it really quickly.

PHIL: How do you keep talented team members?

RYAN: Until you can sell your vision to the technical side, you won’t be able to attract talent. At one point one, of my lead engineers told me that he had been presented with a job offer that he was considering. So I had a conversation with him about our vision, where we’re going, why we were building something huge and why he is critical to the team. He was an absolute key employee at that point. If I hadn’t been able to sell him on that, I don’t know if we’d be close to where we are today.

Edited for length and clarity.

Photo: Bob Kronbauer