Last month, Tommy Donnelly joined BetterCloud as the first chief information officer in company history. He joined the organization after 17 years with Bullhorn (formerly PeopleNet), where he began his career as a QA tester and rapidly climbed the ranks. Most recently, he served as the SVP of Global Security and Information Productivity at Bullhorn, where he managed several teams and a staff of 48 employees.
We recently sat down with Donnelly for an informal chat to get to know him better. Read on to learn more about his career, his leadership strategy, and his vision for BetterCloud over the coming years.
I’m sure you’re tired of doing this after interviewing, but can you give me just a brief summary of your career and how you got to where you are today?
So I started at a company called PeopleNet as a QA tester for our flagship product, which was a time clock. This was really kind of at the dawn of the internet, where everything was done over dial-up. The founder of the company had the foresight to say that, “Hey, we really should have a central portal, and it should live on the internet.” At the time, a lot of companies didn’t even have an internet connection.
We had a website application that people would dial into, either with the modem, directly to us, or they would get on the internet if they had a connection. There was really no one in the company to manage the application website, so I became the person that was maintaining this bank of modems, our servers, and the website. In the early days, there were always a lot of challenges with new technology, so I kind of developed a passion for creatively leveraging new technology and solving these types of problems.
That’s pretty wild to think about how all that was born off of the back of dial-up modems, and especially now that PeopleNet has been acquired by Bullhorn. Speaking of, you were there for most, if not all of your career up until now?
Yeah, I was. I kind of went through the entire ranks at PeopleNet, from QA tester & Support to CIO. I think my greatest strengths were managing the infrastructure and security. We were doing some pretty innovative things with collapsed core networking, security, and virtualization in the early days that provided a very high service level with low operational costs. We had tight margins so we really relied on new technology to reduce costs and make our business model work. I realized that we should apply a similar technology enablement methodology to the rest of the business (not just infrastructure) which really propelled me to the CIO role.
After climbing the ranks at PeopleNet and Bullhorn, what about BetterCloud stood out to you?
The thing that I love about BetterCloud is that it’s a tool for technologists like myself. Being in a role in which I could contribute to the product roadmap in a deeper capacity for a tool I actually use really appealed to me.
BetterCloud and Bullhorn’s products serve vastly different audiences. Do you think your approach to the CIO role will change in any ways? And what aspects of being a CIO just carry over regardless of the company or its market?
If anybody tells you that the role is the same at any company, they’re wrong. It’s always situational, and you need to understand the needs of the company and customers when you’re the CIO. There are always lessons learned and best practices that you can lean on, but it’s really important to have the flexibility to adapt to your environment.
So what are some of the unique needs at BetterCloud that might shape your approach to leadership here?
I think that this is going to be a little bit more of an external facing position with more outward thought leadership. We really need to educate the community about the capabilities of BetterCloud and some of the problems that our technology uniquely solves. I also anticipate interfacing with the sales and marketing teams frequently to fine tune the messaging of our product, to be able to speak the same language of a CIO or other executive technologist.
One thing that BetterCloud and Bullhorn have in common is that they both manage and secure a lot of customer data. Are there any lessons you learned at Bullhorn that you think will pay dividends in your role as you take over the reins at BetterCloud?
Philosophically, you’re doing the same things, but there’s just a lot of differences in that BetterCloud is a 100% cloud native application. Some things that were very difficult at Bullhorn are very simple here and vice versa. There are always trade-offs depending on your infrastructure and every environment has its challenges.
Let’s talk about your philosophies around people management. What was your leadership style before COVID hit, and has it evolved in the months since?
I’m going to go and push a lot of transformation in the organization, as well as some different philosophies around security and technology. So in my orgs, it’s really important to have leaders that can create a vision, foster key relationships and gain cross-functional consensus.
When we go to do transformative projects, sometimes it’s not going to go perfectly the first go around. You have to then iterate to mature and capture the full value of the new technology. Those strong relationships go a long way with getting full adoption across the org. So that’s definitely something that I look for.
It’s super important during this time of COVID, because organizations are having to rapidly change the way they do work. I want people to feel comfortable with bringing challenges that they’re having with the current work environment. We really try to make IT technology problem solvers; we can help solve those problems with technology to try to soften the blow of not being able to sit in the same room with people and use a whiteboard.
When you’re looking at building a team, how do you get top candidates excited to work for you—especially in times like these when the talent pool might be a little more saturated than usual?
Obviously, the skillset is important, but I look for people that can make connections that others don’t see. This type of creativity is key to solving problems with technology. I look for people that want and are willing to learn. The tech skills you need today will be different tomorrow. Finally, I look for people that buy into my philosophies and mission. If you can find people that truly believe in what we’re doing, everything else seems to fall into place.
On a completely unrelated note, I threw this on there as sort of a fun question. Are there any misconceptions about IT people that you just can’t stand and wish would go away forever?
There’s definitely a lot of IT stereotypes that you run across: IT practitioners not being very sociable, that we feel like we’re smarter than everyone else. I would say the one that irks me is the idea that IT is not strategic and our purpose is really there just to keep the lights on. Our goal is to change the paradigm. Our team should absolutely have a seat at the strategic table, we’re technology enablers and if you bring us to that strategic table, we will help everyone to achieve their goals.
We asked Chris Jones this when we interviewed him last year: Where do you see BetterCloud at this time next year? How about five years from now? And do you have any initial thoughts on how the IT org at BetterCloud is going to play a role in that?
I think that we’re kind of at a tipping point where we don’t have to educate people about the value of our product anymore so I think that we could have some explosive growth in the coming years.
The market is kind of coming to us. We have the best product and a strong leadership team so I would hope in five years, BetterCloud will be just like any other tech provider that everyone has heard of and knows what we do, but minimally just knows the name and the space.
I think SaaSOps will be a known practice industry-wide. And as a result, I think most people will recognize BetterCloud—and more importantly, that most technology professionals will know what we do.
I just have one more question for you, which I stole from Rachel’s SaaSOps stories series. What’s the thing you’re looking forward to doing again when we’re through the pandemic?
Travel. I want to go somewhere different and experience their culture and their food. In between Bullhorn and BetterCloud, I rented an RV and traveled around to all the national parks in the United States, which was amazing. But I’m looking forward to being able to travel somewhere and get into the culture of that location. Before this all happened, I was planning a trip to Portugal, so I’m really looking to go there in the near future.