The CTO Journey: Ryan Donovan of Hootsuite

When did you first fall in love with tech? And how did you get into tech as a career?

I fell in love with technology before I started elementary school. My father was in a math-based career that required a lot of computational horsepower - he always had the latest and greatest technology. Then, as a family, we got the original Macintosh and I was hooked. I chose technology as a career sometime between middle school and high school. I realized that (given eyesight) I was not going to become an airline pilot so my love of computers just made sense.

Transitioning to a Manager Role

Some people in our community are thinking about making the transition from a developer to a tech lead / engineering manager / CTO. But many are unsure if they should really make the switch to a more managerial role. Do you have any tips on how to answer the “is this right for me” question?

You have to have a passion for people and business outcomes that exceeds your passion for technology. In the earlier stages of your managerial career, if you aren’t willing to spend as much or more time focused on people and leadership than technology, then this is not the right track.

As you rise through the ranks you have to start to care about business outcomes and deliver on those equally as much.

What was it that you had to learn, back then when you made the transition to a manager?

I found my way as a people leader. If I had it to do over again, I would have prioritized courses and reading on leadership a lot more and much earlier than I did.

What do you consider the most challenging aspects of your role today?

Without a doubt hiring and retaining talent. The demand for technology roles far exceeds supply. So within the constraints of your organization, making it an employer of choice requires relentless laser focus.

Should a CTO Still Code?

Sometimes, there’s a debate about whether a CTO / Tech Lead should still actively develop code. What’s your take on this? Must or can a CTO still reserve some time to code?

I am going to answer this question a bit differently with some advice from a very sage manager from very early in my Microsoft career. He said that as a technology leader, you have to be a super-user of your product/technology. If this is a developer-centric product, then coding as a super-user is a must.

I have found this advice has carried me well throughout my career. That said, I still tinker relentlessly with technology.

On the other hand, of course, not every developer wants to transition into a management role! For those that want to keep developing software: is there any piece of advice you find yourself giving often to the developers on your team?

Work with your leaders to find opportunities to take on more and more challenging technical projects and tasks. There is no reason why in most mature organizations as an individual contributor developer you should not be able to reach the same level as a Senior Director or Vice President. But you will have to work with your leadership to create this path. It won’t happen automatically so you need to be in the drivers seat.

Non-technical Skills Required

Producing code is only one part of the craft of software development. What non-technical skills should a software engineer develop?

Excellent communication skills. Being able to explain complex concepts, requirements, and ideas in an articulate fashion to both technical peers as well as non-technical colleagues is critical.

It’s not a secret that developing software is a team sport. What traits, skills, and habits should an engineering team focus on to become a world class team - and not just a bunch of talented individuals?

I would say invest some time on how you work together as a team. Have clear roles/responsibilities. Invest some time in process and tools.

Think about onboarding and how to get a new colleague up and running quickly.

Being the new kid on a team can be quite intimidating, especially in the face of large code bases and complex processes. How do you help a new developer in your team get up to speed quickly?

At Hootsuite, we always assign an on-boarding buddy to help get you up to speed. And in some cases where we have more complexities, we have developed our own specialized on-boarding programs. This is in addition to corporate and general development onboarding.

Exciting New Technologies

Today’s tech world is brimming with new technologies. Is there any technology or recent development that you’re particularly excited about? Why?

Two things standout for me. At the front-end, the power of today’s mobile handsets is quite remarkable and the ability to create new types of experiences; the sky is literally the limit. To power it on the back-end, serverless lambdas are quite of interest as this gives one a new and modern way to build applications that can scale to massive levels without some of the challenges and complexities of traditional distributed systems architectures.

About Ryan Donovan

Ryan Donovan is the CTO at Hootsuite where he leads our product management, user experience, software development, production operations, program management, customer support, user education, and security teams. He sets the course for defining the underlying product and technology strategies that constitute Hootsuite’s dynamic product portfolio and ensures that customers have a quality experience end-to-end when using Hootsuite’s products.

Ryan is a seasoned product management and engineering executive with a track record of consistently incubating and/or growing successful software businesses with a focus in the B2B, enterprise, and marketing technology spaces. He has established a pedigree of delivering products that successfully service non-technical business personae as well as building extensible, flexible application platforms for developers and IT professionals.

Ryan has over 20 years of experience having held several regional and global leadership roles in Canada and the US. Prior to his role at Hootsuite, Ryan was CTO of Sitecore in a global role. Ryan also headed up commerceserver.net as President and CTO, Ascentium Corporation (now SMITH) as Co-President and CTO, headed up all engineering, product operations at Cactus Commerce in Ottawa and spent over 8 years at Microsoft.

You can follow Ryan on LinkedIn, Twitter, Instagram, and read his Blog.

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