CIO Spotlight: Thomas Donnelly, BetterCloud

Does the conventional CIO role include responsibilities it should not hold? “CIOs are turning into COOs. You need to have a higher understanding of the business goals so you can be a force multiplier for every department using technology.”

Headshot of Thomas Donnelly, CIO at BetterCloud

Name: Thomas Donnelly

Company: BetterCloud

Job title: CIO

Date started current role: September 2020

Location: Atlanta, GA

Tommy Donnelly serves as the Chief Information Officer, where he is responsible for the company’s Information Technology, Enterprise Applications, Customer Support, Security and Compliance functions. Donnelly brings two decades of experience in IT, security, infrastructure, privacy, compliance and technical strategy across SaaS environments. He joins BetterCloud from Bullhorn, a global leader in software for the staffing industry, where he served as the SVP of Global Security and Information Productivity with global ownership over Security, Compliance, Privacy, Information Technology, Enterprise Applications, Data Science and Technical Project Management

What was your first job? I was a QA Tester for a startup time & attendance company, Peoplenet, which was acquired by Bullhorn. This Internet thing was fairly new at the time, and we were an early pioneer of SaaS before it was called SaaS. Part of my job was managing a bank of modems so customers could dial in if they didn’t have an Internet connection yet!

Did you always want to work in IT? I grew up wanting to be an architect–of buildings, not software. Once I got into technology, I loved the pace of change and how there was just an endless amount of things to learn. I love how you can use your creativity. There are so many building blocks of technology you can pull together to transform the business.

What was your education? Do you hold any certifications? What are they? I went to school for business and then went on to earn an MBA. I don’t think it is super important to get a technology-related degree. Things change so quickly, the most important thing is that you have to be willing to continually learn and continually question the status quo. My college calculus teacher told me the most successful people “continually fight the ghosts of mediocrity.” That really stuck with me.

Explain your career path. Did you take any detours? If so, discuss. No detours. I bounced around in many different departments before taking over all of IT, Security, SRE & Business Systems. Looking back there are really two things that really stick out as helping me be successful in technology. 

First, I started out as a jack of all trades (QA, IT, Networking, DBA, SRE, Business Systems, Development). Having that broad experience helped me build a deeper understanding of how technology works and that really helped me throughout my career.

Second, working for a small company with very limited resources forced me to be extremely creative in how I solve problems and leverage technology.

What business or technology initiatives will be most significant in driving IT investments in your organisation in the coming year? We are pushing the limits of zero-touch IT using our own product, BetterCloud. This not only makes us more efficient and creates an amazing employee experience but it is a powerful message back to all BetterClouders on how powerful our platform can be. It really gets our employees excited to be working at BetterCloud.

What are the CEO's top priorities for you in the coming year? How do you plan to support the business with IT? Building a high performance culture. If you do that, everything else seems to fall into place. We strive to understand what the business departments need to achieve, and keep up with – and anticipate –  their requirements. 

Does the conventional CIO role include responsibilities it should not hold? Should the role have additional responsibilities it does not currently include? CIOs are turning into COOs.  You need to have a higher understanding of the business goals so you can be a force multiplier for every department using technology.

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? For us, revenue growth is paramount. Luckily, we provide tools for IT so there is a high value on demonstrating how we can transform the business with our own product. I guess you could say it is somewhat more balanced than most companies.

Describe the maturity of your digital business. For example, do you have KPIs to quantify the value of IT? At BetterCloud, we have a Tech Scorecard for each department. It measures how they are using automation, leveraging data and grades the department’s tech stack. We use these scorecards to help build a roadmap to mature each department's technical capability.

What does good culture fit look like in your organisation? How do you cultivate it? It’s part of the employee experience during their entire time at BetterCloud. We implement a values interview process. It is part of the bi-annual review process. We have a Slack channel where people post when teammates demonstrate the key cultural values and put them into action. At the end of the month, the ELT selects people who most effectively demonstrated our cultural values with Crushing IT awards presented in our all-hands meeting. 

What roles or skills are you finding (or anticipate to be) the most difficult to fill? Application Security people and compliance. It’s not just difficult to find the right skill level, it’s also costing crazy amounts of money. Most important is that every role needs an ability to automate. Just about every job has some aspect of automation - which means everyone will need at least light coding ability. That greatly increases their ability to execute. Marketing people need to automate. Every person on our security team can write code. Everyone needs both domain knowledge and the technical knowledge to take it to the next level. Those are the people I want to hire, and they are hard to find these days. 

What's the best career advice you ever received? The CEO of Peoplenet, the first company I worked for, often reminded me to do two things. Listen more, and talk less. He also encouraged me to take an empathetic approach before making decisions, especially when coming in as a new leader.

Do you have a succession plan? If so, discuss the importance of and challenges with training up high-performing staff. It’s harder to talk about succession in a smaller company, where resources are more constrained, and so much is about getting the right leaders in place. As CIO, I really encourage my leaders to operate without me. They should be able to do that, to handle execution, and I should be somewhat external and visionary. 

What advice would you give to aspiring IT leaders? Understand the business, and have specific business goals, not just IT goals. Tie your work back to business results. Also, very important, IT leaders need to build the relationships to execute cross functionally. 

What has been your greatest career achievement? At Peoplenet, our infrastructure ran at just 3% of revenue with 99.99% uptime. At other companies, that would be 10% or even 20%, with much poorer uptime.  Our business worked because we were really good at running infrastructure, responsible for paying billions in payroll. To achieve that, we used very cutting edge technology. I like to push the limits at the bleeding edge. Actually, the CEO once asked me, “Do your hands always have to be bleeding? Why are you always handling cutting edge tech?” 

Looking back with 20:20 hindsight, what would you have done differently? I would have focused early in my career on becoming a better communicator. That would have made me more successful in certain areas. It’s possible to get far ahead in technology, but to bridge the gap with where we currently are, leaders need to share a vision of where it’s going. 

What are you reading now? I’m reading a biography on Beethoven.

Most people don't know that I… love art. Modern art in particular.

In my spare time, I like to…First off, playing with my kids; I have 7-year old twins. I recently got back into skateboarding. For athletics, I play a lot of soccer, and for an executive sport, I do play golf. And yes, I am honest about my handicap.

Ask me to do anything but… be disloyal. I am highly loyal – to a fault.