CIO Spotlight: Deb Gildersleeve, Quickbase

Does the conventional CIO role include responsibilities it should not hold? “One thing I think successful CIOs embrace is business skills like partnering with different line of business users.”


Name: Deb Gildersleeve

Company: Quickbase

Job title: CIO

Date started current role: June 2020

Location: Boston, MA

Deb Gildersleeve is Chief Information Officer of Quickbase, which provides a business application development platform that helps businesses achieve operational agility, freeing enterprises to flex and evolve by safely connecting people, information and ideas everywhere.

What was your first job? My first job was working in technical support for an ERP/ supply chain software company.

Did you always want to work in IT? Yes and no. Growing up, my favorite subjects were science and math. I wasn’t quite sure what that translated to in terms of a career until I started my first co-op in college in an IT department. From that point, it was clear that my career would be in IT.  

What was your education? Do you hold any certifications? What are they? I received a Bachelor’s degree in Applied Mathematics from RIT. I then went on to receive my Masters in Information Systems from Northeastern here in Boston

Explain your career path. Did you take any detours? If so, discuss. I started my career in consulting and did that for about 9 years. That allowed me to work with many people and in many IT departments. Consulting has been a great jumping point for my career and allowed me to build leadership, IT and business skills across a number of different teams and organisations. I then worked in IT leadership at Gartner for nearly 12 years, which really set the foundation for where I’m at now. I did take the opportunity to work for a small startup, which was a really great learning experience and ultimately led me to my role now at Quickbase.

What business or technology initiatives will be most significant in driving IT investments in your organisation in the coming year?  Like most IT leaders, my big initiatives over the last year and in the coming year are focused on helping teams work efficiently amidst this wide scale disruption we’ve experienced. Whether it’s finding ways to continue driving digital transformation, maintaining business continuity, embracing a hybrid work model, and overall making sure the organisation has the tech tools they need to do their jobs effectively and safely. 

What are the CEO's top priorities for you in the coming year? How do you plan to support the business with IT? As a growing, private company, one of our main priorities is growth. I come into this by making sure our teams have the tools and systems in place to do their jobs efficiently. Another area is continually working to improve the access to data across the organisation and using it to drive actionable insights for our business.

Does the conventional CIO role include responsibilities it should not hold? Should the role have additional responsibilities it does not currently include? One thing I think successful CIOs embrace is business skills like partnering with different line of business users. Especially in my role, that is so important and is something CIOs should do even if it’s not in the “job description.” Overall, it will make you better at your job and will help your organisation cross-functionally

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? Both are at play. Working for a company that’s dedicated to helping organisations achieve operational efficiency and agility, I’m in an interesting situation. We’re of course trying to drive revenue growth and our customers are at the heart of what we do, but we also practice what we preach. It’s very twofold and both are so important for organisations to truly focus on digital transformation. At Quickbase, one thing we really focus on is the notion of a dual-track approach, where you’re focusing on the large-scale transformation AND rapid-cycle innovation (i.e the quick wins and ability to pivot quickly) - it’s not either or, but how to do them both, together.

Describe the maturity of your digital business. For example, do you have KPIs to quantify the value of IT? Quickbase is mature and robust as they have been serving customers for more than twenty years - we’ve helped more than 6,000 companies empower their business users to solve their problems and create digital solutions. We’re constantly looking to grow and not only reach more customers but help organisations we currently work with expand their use cases. The beauty of no-code / low-code tools is that the possibilities are truly endless, so we’re all about working with organisations to help them unlock the potential of their business users.   

What does good culture fit look like in your organisation? How do you cultivate it? One of the big things within our organisation is empowering employees and business users. As an IT leader, that means giving everyone the tools and systems they need to do their jobs and providing the governance and oversight to do so. It’s also about fostering a culture of collaboration, and especially as we live in a remote world now, finding tech and tools like Zoom, Slack, Sharepoint, Trello, etc. to help encourage collaboration and engagement when we may have previously been working at a whiteboard over lunch in a conference room.

What roles or skills are you finding (or anticipate to be) the most difficult to fill? The IT backlog is well documented - IT and security roles are difficult to fill and will continue to be. It’s interesting because in my role as an IT leader, I’m also working to help other IT teams empower users outside of IT to solve their problems because of this huge IT backlog, and quite frankly, not every single application or system needs to be built by IT. While their oversight is 100% necessary and that’s part of their role, there are ways to use tools, like the ones the organisation I work for create, to fill the gap where roles are hard to fill.

What's the best career advice you ever received? Work with the business to help solve their problems. Technology is best used to solve or get ahead of problems for the business. As much as we technologists love to learn and work with the latest and greatest technology out there, it is rarely successful if it isn’t solving a business need or bringing the business forward in some way.

Do you have a succession plan? If so, discuss the importance of and challenges with training up high-performing staff. That is something I’m always working on. One of the most difficult aspects I’ve often seen is around letting go of the day to day in the technology. It is so important for technology leaders to multiply their reach by working with their teams not only on the technology but also on learning the business, problem solving and leading others.  

What advice would you give to aspiring IT leaders? Learn new areas whenever possible. Opportunities to learn different areas of technology or the business give you different perspectives that make you a more well-rounded IT leader.

What has been your greatest career achievement? I think the greatest achievement for any leader is to see people you’ve managed and mentored throughout your career grow into leaders themselves and even become peers within an organisation.

Looking back with 20:20 hindsight, what would you have done differently? 2020, while was challenging in many ways, professionally was a good year for me - I started as CIO at Quickbase. Since we weren’t in an office when I started, I could have done more informal meetings, and there are some people I should have met sooner, but overall there isn’t a lot I would change.

What are you reading now? I just started reading Ask for More: 10 Questions to Negotiate Anything by Alexandra Carter.

Most people don't know that I… Dropped my first programming class as a freshman in college! It wasn’t until my first co-op later that I really started diving more into IT.

In my spare time, I like to…Explore new areas with my dog. I’m a New England native, but I recently moved back to Boston, so I’m always looking to explore new areas. I’m also a big sports fan (baseball and football), and am hoping we can get back to some live events this year. I, like many, also can’t wait until we can safely travel again.

Ask me to do anything but… Cook anything with more than 5 ingredients.