CIO Spotlight: Darlene Williams, Rocket Software

What's the best career advice you ever received? “Be a learn-it-all instead of a know-it-all.”

Headshot of Darlene Williams, Senior VP & CIO at Rocket Software
Rocket Software

Name: Darlene Williams

Company: Rocket Software

Job title: Senior Vice President and Chief Information Officer

Date started current role: April 2022

Location: Waltham, Massachusetts

As Chief Information Officer, Darlene Williams is responsible for developing and executing digital innovation transformation strategies essential to Rocket Software’s success. Williams has more than 20 years of experience in IT strategising and delivering large-scale business and technology transformations across multiple industries. She first joined Rocket Software in December 2021 as interim Chief Information Officer. Prior, Williams held technology leadership roles at Arisma Solutions LLC, serving large private equity firms.

What was your first job?  My first job was working for my dad at his food truck selling hot dogs, chips, and soda.

Did you always want to work in IT? My first job out of college was with Xerox, a technology company. I find technology interesting. All of my jobs – across a variety of industries - have entailed a technology component.

What was your education? Do you hold any certifications? What are they? I received my bachelor’s degree in business from Florida State University and an MBA in business administration from Nova Southeastern University. I hold a number of certifications, including:

  • Prosci Methodology Application Program certification
  • Certified SAFe 5 Agilist
  • MIT Sloan Executive Education - Leading Through Financial Excellence certification
  • Columbia Business School’s Building and Leading Effective Teams certification

Explain your career path. Did you take any detours? If so, discuss. Yes. Because of my growth mindset, I’m naturally curious and enjoy learning and applying my skills to achieve organisational success. For that reason, my career journey has been an interesting one that has spanned multiple verticals, from management consulting to home building to utilities to technology companies.  

What business or technology initiatives will be most significant in driving IT investments in your organisation in the coming year? Initiatives that increase automation and streamline business processes to improve employee and customer experience will take priority.

What are the CEO's top priorities for you in the coming year? How do you plan to support the business with IT? Its priority is to align with Rocket Software’s overall strategic direction and to enable our internal team of experts to develop and deliver modern solutions that help our customers solve their complex technology challenges simply and without disruption.

Does the conventional CIO role include responsibilities it should not hold? Should the role have additional responsibilities it does not currently include? I believe every CIO should hold the responsibility of playing an active role in improving their company's culture. Just as CIOs drive innovation in digital transformation strategies, they should also drive originality and inclusion in their company’s culture.

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? I am leading a transformation of IT to allow Rocket Software to scale our business for organic and inorganic growth. In order to do so, we continuously improve operational efficiencies that ultimately help our customers.

Describe the maturity of your digital business. For example, do you have KPIs to quantify the value of IT? Yes – we measure key performance indicators of IT operations including service desk metrics, project delivery ROI, employee net promoter scores, to ensure we are delivering against business requirements and success outcomes for the organisation.

What does good culture fit look like in your organisation? How do you cultivate it? Rocket Software truly prioritises building a culture of inclusion and creating an environment where team members have the opportunity for career advancement and long-term career success. One of the reasons why I came to Rocket is to build upon their efforts to cultivate a work environment where employees feel excited and valued, and where leaders are actively and purposefully engaged in their respective departments.

What roles or skills are you finding (or anticipate being) the most difficult to fill? We are doing well finding talent in this tight market. I believe our success is attributable to our strong company culture and core values of humanity, trust, empathy, and love.

What's the best career advice you ever received? Be a learn-it-all instead of a know-it-all.

Do you have a succession plan? If so, discuss the importance of and challenges with training up high-performing staff. Yes - I believe succession planning is core to developing our people. Identifying who wants to move up and across the organisation, upskilling them and giving them opportunities to lead initiatives are good ways to develop and inspire the next generation of leaders.

What advice would you give to aspiring IT leaders? Actively listen to people at all levels of the organisation to seek understanding. Be a learn-it-all instead of a know-it-all.

What has been your greatest career achievement? My greatest career achievement is having the courage to say “Yes” to different career opportunities where I have had the privilege to work alongside so many talented and passionate people.

Looking back with 20:20 hindsight, what would you have done differently? I have no regrets about my career decisions. I’ve learned and grown through every experience.

What are you reading now? The Four Agreements by Don Miguel Ruiz.

Most people don't know that I… like to bake.

In my spare time, I like to…read and spend time with my family.

Ask me to do anything but… pick up frogs.