CTO Sessions: Ryan Donovan, Hootsuite

Which emerging technology are you most excited about the prospect of? “We’re starting to see cross platform UI frameworks really mature so you’re getting closer to the ability to write once and deploy everywhere across all devices and form factors.”


Name: Ryan Donovan

Company: Hootsuite

Job title: Chief Technology Officer

Date started current role: February 2019

Location: Seattle, Washington + Vancouver, Canada

Ryan Donovan is the CTO at Hootsuite where he leads the product management, user experience, software development, production operations, program management, user education, IT 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. Donovan has over 25 years of experience having held several regional and global leadership roles in Canada and the US.

What was your first job? I started my first job at 12 years old fixing Apple 2C’s and Apple 2E’s for my middle school after school. It was a great opportunity to learn software and hardware and get paid to do it. It was also a nice way to help the school because I was certainly a lot cheaper than an authorised Apple repair facility person.

Did you always want to work in IT? I originally wanted to be an airline pilot but then discovered my eyesight wasn’t well suited for that career. Technology was my next love and I fell into that pretty early on. I knew by the time I was fixing those Apple 2Cs and 2Es that’s what I wanted to do.

What was your education? Do you hold any certifications? What are they? In school, I was drawn to math and science and anything to do with computers. In university, I started out majoring in computer science but then realised that it was still the early days for computers. The University of Washington didn’t have a well-regarded computer science program at the time. The benchmark was: could you get an interview with Microsoft? In my case, the answer was no, so I switched to major in business. Then timing being everything, Bill Gates donated $55 million dollars to fix the computer science program a year later.

In 1998, I had the opportunity to work with a lot of the senior leadership working on the launch of Windows 2000. It was incredibly valuable because I was able to learn from the people that made Microsoft what it was. Looking back, it was one of the most enjoyable things I have ever done. Post Microsoft, I worked for smaller and medium sized companies and had to be a lot more resourceful, which led to me finding my passion for reading. I am a voracious reader and read dozens of industry blogs every day. I’m always reading a new book on best practices in business or software engineering.

Explain your career path. Did you take any detours? If so, discuss. When I was in college, I started my own consulting business to help clients get on the web. I thought that was what I was going to do forever but then I learned a harsh lesson - one of my clients went bankrupt and I wasn’t paid for several months of work. So, I decided the corporate life would be better and went to work for a web agency that eventually became part of Sapient Publicis. One of the projects they hired me for was building the first online investment portal for Royal Bank of Canada, the Dain Rauscher division. It was one of the first big projects on Microsoft technology that was high profile. That was how I ended up getting to know the people working on Windows at Microsoft and was recruited by Microsoft after the project was complete.

After almost 9 years at Microsoft, I moved to Ottawa, Canada and worked at Cactus Commerce where I was responsible for running all of the operating divisions. After being acquired by Ascentium, while I was the global CTO, I also had to also wear the hat of co-president because the CEO and COO had both departed the company. I found myself reporting directly to the VC who had a big stake in the business.

One of the projects at Cactus Commerce was focused on outsourcing the development arm for Microsoft’s eCommerce portfolio. I had followed that product line all the way through from my time working at Microsoft - minus a year running commercial web hosting.

In 2011, Microsoft decided to stop having SharePoint focus on internet facing sites, and of course, Commerce Server was wedded to SharePoint, which meant Microsoft was getting out of that business. As part of the wind up of the contract, Ascentium was able to get a license of the IP. Ascentium’s VC directed me to make it into a company and sell it - so we did. Eventually, we sold the software business to Sitecore. I ran R&D at Sitecore for a few years and saw it all the way through to a successful private equity exit with EQT. I ended up staying around for the next few chapters with the new owners, but I found myself looking for a new adventure. That’s when Hootsuite came knocking and that was an opportunity I couldn’t turn down.

What type of CTO are you? There are multiple flavours of CTOs. So, you have the CIO in disguise, the chief architect, the traditional head of engineering, the chief evangelist, and the product general manager.  I’m definitely in the latter category but have quite a responsibility for our IT since it’s woven into our SaaS platform.

A more accurate job title for me would be Chief Product and Technology Officer, since I spend just as much time on product strategy as I do on things like architecture and engineering best practices. It’s one of the most fun and cool jobs in the world. 

I’ve been running engineering and product disciplines my entire career. Having empathy for the team has been very important. It helps keep us united and going in the right direction because I can appreciate the perspective of a product person just as much as I can the engineer. Oftentimes, what's important to each of them can be in diametric opposition to one another, so having that perspective helps me make the right decisions and foster a more cohesive team.  

Which emerging technology are you most excited about the prospect of? We’re starting to see cross platform UI frameworks really mature so you’re getting closer to the ability to write once and deploy everywhere across all devices and form factors. This eliminates the need for multiple disparate codebases across different device form factors.

Are there any technologies which you think are overhyped? Why? I think VR/AR are not quite there yet. There are a lot of pioneering efforts but they haven't gone mainstream. I haven't seen any killer use cases that make me say “I have to have it” but it’s coming and it will get there.

What is one unique initiative that you’ve employed over the last 12 months that you’re really proud of? Starting Hootsuite’s focus on digital enablement. If you think about how a brand differentiates itself, it can be based on innovation, price, or customer intimacy. At Hootsuite, we’ve put an emphasis on the customer intimacy piece. And now we have to deliver upon that value proposition. 

One of the unique things about Hootsuite is we have the largest customer base of solopreneurs to Fortune 50 businesses doing social media in any one place across all of the networks. Being able to harness the power of that customer base in a digital first fashion helps people become more effective social practitioners. It also allows us to harness the power of data in unique and novel ways and differentiate our customer service in a way I don’t see others doing. Any social discipline, whether that be social marketing, social selling, social-based customer care - are relatively new so most companies need guidance on how to implement these tools across the organisation. We have to educate them on the art of the possible and help them realise that it's a unique and critical opportunity. 

Are you leading a digital transformation? If so, does it emphasise customer experience and revenue growth or operational efficiency? If both, how do you balance the two? If done right, I think one leads to the other. Delivering the best customer experience will drive revenue growth because people will want more of it. For Hootsuite, from a digital transformation perspective, going down this journey has caused us to build muscle mass around data analytics and data science. It’s a very exciting time for us and a huge opportunity to build this muscle up. We’re early on in our journey and it’s absolutely the right bet. We’re sitting on a dataset that’s second to none other in the world. 

The art of product management is to always ruthlessly prioritise the most important things and be as focused as possible. So, if we really think about our product roadmap overall, there are four key priorities. We have our four key use cases, including social marketing, social selling, employee advocacy, and social customer care, and then data under the hood and that manifests itself in terms of digital enablement.

What is the biggest issue that you’re helping customers with at the moment? I would say getting our customers started on social media. From there, once our customers are up and going, it’s about helping them get more active and engaged, helping them mature, and then helping them branch out to the more advanced capabilities so they become that much more of an expert practitioner. And if they start to fall back, we’ll be there to catch them.

How do you align your technology use to meet business goals? I like to dabble in all the major platforms because our customers use different technologies and I want to make sure I’m walking in their shoes as much as possible. Even though macOS, for example, is my primary operating system, I still use Windows. That’s why I have an Android phone in addition to my iPhone. And a Chromebook. Obviously, I want to work within the realm of the technology that we officially support from an IT and security/compliance perspective. If there is a gap in something I need to use, I work with the IT team to find a point solution to fill that gap that still plays nicely with the rest of our technology from a security perspective. 

Do you have any trouble matching product/service strategy with tech strategy? Product/service strategy and tech strategy are oftentimes inherently at odds with each other. It's a constant ongoing challenge. I try to arbitrate the differences and find synergy. If I want to build a certain piece of functionality in a certain area, I use that as an opportunity to retire a piece of technical debt while the proverbial hood is open. Trying to do that match-making is the best way to manage it, but it’s an ongoing juggling act. It requires a solid understanding of the feature set and the underlying architecture to match the business work streams with the technology work streams.

What makes an effective tech strategy? It has to be fully in support of the business goals. There can’t be large amounts of work that doesn't contribute to business objectives. And, you have to remember what business you’re in. That is something a lot of companies struggle with is they will end up building tech for the sake of building tech. 

What predictions do you have for the role of the CTO in the future? I think you’ll see more roles like mine, whether it’s called CTO, CPO or CPTO, where you’re making sure you have a seamless fusion between your product teams and your technology teams. It’ll become more common than it is today. A lot of CEOs are struggling right now with the convergence between the two. To do it right, it’s a full-time job and a lot of companies are starting to wake up to that fact. 

Whatever flavor of CTO, there is going to be a lot more work to be done to realise the value and opportunities afforded by the changes that are happening right now. It’s also about making sure, no matter what industry you’re in, that you’re thinking about those impacts and what they can bring to the table.

What has been your greatest career achievement? My legacy at Sitecore. It went from being a single product company to a multi-product company. It went from being on premise to cloud and set up a portfolio that covered the entire spectrum from content creation, all the way to delivering it on an eCommerce storefront and everything in between. Then differentiating it with market leading analytics and personalisation - it was a novel thing to have that integrated into what’s now known as a DXP. Sitecore was a first mover there. This all happened within a four-year timeframe with the help of my great team and visionary and supportive set of co-founders. 

At Hootsuite, I am most proud of our UX refresh in 2020 along with the ongoing success of Amplify as a social selling and employee advocacy platform, and now the acquisition of Sparkcentral. 

Looking back with 20:20 hindsight, what would you have done differently? One lesson I’ve learned along the way is to understand the types of environments you really need to be in to be successful. That is not only from corporate strategy to growth strategy but it’s also about culture and people. I’ve learned what works for me and what doesn’t and had I known previously what I know now, I would’ve made moves at different points in my career instead of waiting things out.

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