Exit strategies: Late-career IT leaders forge post-CIO paths

CIOs and other technology leaders are accustomed to facing difficult challenges. Many of them have been doing so for most of their careers. And the hurdles don’t go away as these executives enter the late stages of their careers. They just change.

Late-career IT leaders face challenges such as an underestimation of their ability to learn about new technologies and keep up with rapid technological changes, general age-related biases, and others. For those who have been laid off, finding a new position can be especially daunting due to a tight market, ageism, and competition from younger technology executives.

Here’s how four IT executives have handled their late-career challenges.

[ See also: IT’s silent career killer: Age discrimination ]

The value of planning ahead

Bill Balint, former CIO at the Indiana University of Pa. (IUP), spent 36 years working full time in the IT industry. His first year was with the Internal Revenue Service; the final 35 were with IUP.

For his initial eight years at IUP, Balint was a systems analyst. From there he worked his way through various levels of IT management, before becoming the university’s first-ever CIO, a position he held for 18 years at IUP while concurrently serving as a technical executive for the Pennsylvania State System of Higher Education for the final 11 years.

Following his retirement from IUP in 2024, Balint founded a part-time higher-education IT consulting practice called Haven Hill Services, and has been working successfully in that space for the past year.

“I was not ready to leave the industry at age 59, even though I received a full state pension,” Balint says. “My goal was to continue working in the higher-education IT executive-level space, only on a part-time basis as a contractor as opposed to an employee. Upon further consideration, I narrowed my choices to contracts that were mainly remote and those with some predictability in terms of time commitment and contract length.”

The biggest challenge in making this work was having to “thread the needle” due to those preferences, Balint says.

“I quickly learned I would have to surrender most of these if I attached myself to a large-scale firm, where most of the opportunities exist,” he adds. “Opportunities that fulfilled my preferences found their way to me, but I was admittedly very fortunate that this happened.”

Another challenge was learning how to operate as an independent consultant, including gauging market conditions and figuring out how much to charge clients, what contract stipulations to include, how to create an LLC, what the tax implications would be, and so on. “A lot of time was needed to get these pieces in place,” Balint says.

As a first step in planning a late-career strategy, Balint recommends that technology chiefs create a transition plan two to three years before retiring from their existing position. “Knowing how long I needed to transition and how much revenue I needed until I fully retired dictated how strict I could be in adhering to my work preferences,” he says.

From there, Balint set his transition beginning and end dates and focused on what the specifics would look like. This came down to answering five key questions:

• How many hours would he be willing to work per month?
• How much travel and onsite work would he be willing to do?
• Would he be willing to work in industries other than higher education?
• Would he be willing to work as an employee or only as a contractor?
• What areas of IT consulting did he think he could be successful in performing?

“Each time I receive an inquiry for my services, I see how it aligns to those answers and it has been successful so far,” Balint says.

Share the wisdom

Over some 22 years as CIO at global law firms and holding senior positions in IT transformation and services organizations, CIO 100 Award winner Steve Agnoli successfully led business and IT transformation initiatives, ensured returns on technology and process investments, and built multi-disciplinary teams in global environments.

Most recently, Agnoli served as the CIO at the international law firm Reed Smith, leading global IT strategy, firmwide systems operations, process improvement, and new technologies development. Prior to joining Reed Smith, he was head of global IT transformation for Mylan Pharmaceutical (currently known as Viatris), and prior to that served as

CIO at K&L Gates, one of the world’s largest legal firms.

In 2024, Agnoli left his post at Reed Smith to form a consulting firm, SWA Executive Consulting, where he leverages his executive and technology leadership experiences to help client organizations improve their performance through effective technology and processes. This includes providing fractional CIO services and conducting assessments of IT strategy, infrastructure, and cybersecurity approaches.

In addition, Agnoli — who considers himself semiretired — is the lead instructor at Carnegie Mellon University’s (CMU) Chief Information and Digital Officer Executive Program, which prepares technology and business executives to be effective leaders.

“In this phase of my career, I am focused on using the skills, experiences, and lessons I’ve learned over more than 40 years in IT and business fields to help organizations build better digital and IT capabilities, be more adaptable and agile in their processes, [and] ensure business value from technology investments,” Agnoli says.

Through his role as an instructor at CMU, Agnoli is teaching and mentoring the next generation of IT leaders. “Overall I look to take my experiences and turn them into something useful for those who are building their careers in business and technology fields,” he says.

Agnoli’s advice for late-career CIOs: Evaluate what you have done with your career and focus on the areas of greatest skill, differentiation, value add and enjoyment. 

“Then build a way to bring those capabilities into use for someone else’s benefit,” he says. “Time is short; don’t waste time on things you don’t enjoy but rather focus on the things that are of most value to others and of most enjoyment to you.”

Get on board

Over her career, Lisa Roger has proven to be an accomplished senior executive with extensive experience in leadership, business transformation, and IT strategy development. She considers her current role as vice president and CIO at Modern Technology Solutions — an engineering services and technology company — to be her final full-time position.

Prior to this Roger served as CIO at technology solutions provider Oteemo and construction engineering firm Dewberry.

“My current role offers sufficient challenges to keep me engaged and continually learning for the next three to four years,” she says, adding that shifting from full-time work to full-time retirement will involve a transitional period. “The primary challenges associated with this transition include tax management, obtaining affordable healthcare, and ensuring revenue stability, which is particularly crucial during the initial years of retirement.”

During the transitional phase, Roger plans to serve as an independent director on corporate boards and join advisory boards related to workforce development.

“The challenge I face is similar to when I first entered the C-suite: securing that initial board position as a compensated independent board member,” Roger says. “This role typically requires quarterly in-person attendance at meetings, along with several weeks of preparation involving content review, content curation, and formulating leadership and mentoring questions to effectively influence at the board level.”

Serving on one or two boards can adequately address Roger’s financial needs without the demands of a 40-hour workweek, she says.

Like other late-career CIOs, Roger has had to deal with ageism. “I’ve faced challenges related to age and staying relevant,” she says. “As a woman who started in the tech field back in 1989, I’ve shown I can handle it by delivering great results, understanding the workplace dynamics, networking well, and being kind. These strategies work just as well today as they did 40 years ago.”

For example, consistently exceeding expectations and hitting targets helped Roger prove her skills and gain trust from colleagues and bosses. “Understanding the workplace dynamics meant knowing how things work in the organization and aligning my goals with key stakeholders,” she says.

Networking diligently helped Roger build strong professional connections, get valuable insights, and open new opportunities.

Most important, Roger says, is treating others well. “People and therefore opportunities are attracted to people who are positive and nice,” she says. “When you do fall down, which you will, you will have an ‘army of the willing’ to pick you up. It provides an effective shield to protect you when you need it.”

Over the years, Roger has seen huge changes in technology and workplaces. “Yet, these core strategies have always been reliable, helping me stay relevant and make an impact in a constantly changing industry,” she says. “By continually adapting and applying these principles, I’ve managed to navigate through different stages of my career — from entry-level roles to leadership positions — while maintaining growth and personal fulfillment.”

Roger’s advice to any executives approaching the late-career stage and seeking board positions is to avoid waiting until retirement to begin searching for paid board roles.

“The concept of the ‘rule of 72’ remains prevalent; it suggests that board members are expected to retire at age 72,” Roger says. “Therefore, seeking board assignments in your late 50s is optimal timing. Additionally, investing in preparation is crucial. I recommend exploring resources like the National Association of Corporate Boards, which offers comprehensive training programs tailored to meet individuals where they are and prepare them for board service.”

Go the interim route

One option for late-career CIOs is to serve as technology leaders on an interim basis. That’s the strategy Bruce Taggart has taken. After serving as a CIO for about 26 years, he took some time off to travel. Following that, he went back to work as a fill-in technology executive at Oregon Institute of Technology and Juniata College.

Taggart is currently balancing his time between being the interim assistant vice president and CIO at Worcester State University and serving as board chair for the Pennsylvania Research and Education Network (KeystoneREN).

Before working as an interim CIO, Taggard was a technology leader at Lehigh University for about 20 years, holding the title of vice provost of library and technology services. He was responsible for the overall strategic direction, planning, and management of the campus libraries, faculty development, academic and research information technologies, administrative enterprise systems, and graduate-level distance education programs.

Taggard had held an executive IT position at Portland State University prior to moving to Lehigh.

During his time as a CIO, Taggard saw the role shift from technical expert to more of a strategic leader and planner, responsible for the direction and growth of the IT organization. “Key growth and development responsibilities are not the latest technologies, but organizational development and IT staffing, connection with the campus leadership and strategic plan of the university, and knowing where the higher-education landscape is going,” Taggard says.

Like other senior-level executives, Taggard has faced the challenge of ageism. “In my situation, having been semiretired and [deciding] after three years to get back in the higher-education CIO consulting world, there was and is an age bias among the top colleges and universities,” he says.

Prospective employers have questioned Taggart about what he can bring

that’s new or innovative at “this stage” of his career, he says.

For late-career CIOs looking for new opportunities, Taggart suggests it will not be years of IT management that makes them attractive. Rather, it will be demonstrated skills in leadership, strategic planning, and visionary thinking, among others.