The challenges facing CIOs and other tech leaders don’t disappear as their careers progress. they simply evolve. Late-career IT leaders often find their ability to learn new technologies and adapt to rapid change underestimated, or encounter age-related biases. When job displacement occurs due to restructuring, the situation is compounded by a shrinking market, age discrimination and competition from younger tech executives, making re-employment particularly difficult.
Several IT executives shared their experiences navigating these late-career challenges.
“Prepare 2-3 Years in Advance”: The Value of Proactive Planning
Bill Ballin, former CIO of Indiana University of Pennsylvania (IUP), spent 36 years in the IT industry full-time. He began at the U.S. Internal Revenue Service and then spent 35 years at IUP, progressing through IT management roles after an initial eight years as a systems analyst. He became IUP’s first CIO and served in that role for 18 years, concurrently holding a technology executive position within the Pennsylvania State System of Higher Education for the last 11 years.
After retiring from IUP in 2024, Ballin launched ‘Haven Hill Services,’ a part-time higher education IT consulting business, and has been steadily working in that capacity for the past year. “At 59, I wasn’t ready to leave the field. I wanted to continue working in the higher education IT executive space, but as a contractor, part-time, rather than an employee,” he explained. “I narrowed my focus to remote-centric engagements with predictable hours and contract durations.”
Finding that “sweet spot” proved challenging. Ballin quickly realized that joining a large consulting firm would require compromising on most of his preferences. “The opportunities were there, but I’d have to give up most of what I wanted. I did find the type of opportunity I was looking for, but I was also very lucky,” he said.
Becoming proficient in the mechanics of working as an independent consultant was another hurdle. He needed to learn how to gauge market rates, determine appropriate billing amounts, structure contracts, establish an LLC, and navigate tax implications – essentially mastering the “basics of running a business.” “It took a significant amount of time to get all those pieces in place,” Ballin noted.
A key first step in any late-career strategy is to begin planning for the transition 2-3 years before leaving a current position. “Knowing the timeframe and the income needed to fully retire allows you to determine how strict you can be with your work preferences,” Ballin explained.
Once he established a start and end point for the transition, Ballin focused on clarifying the specifics. This involved answering five key questions:
- How many hours per month are you willing to work?
- How much travel and on-site work are you willing to accept?
- Are you open to working outside of higher education?
- Will you work as an employee, or only as a contractor?
- In what areas of IT consulting can you deliver value?
“I’ve been using those answers to screen inquiries, and it’s worked well so far,” Ballin said.
“Experience is an Asset”: Sharing Wisdom
Steve Agnoli, who served as CIO for approximately 22 years at a global law firm and held senior positions in IT transformation and service organizations, has a track record of leading business and IT transformations, ensuring technology and process investment returns, and building multidisciplinary teams in a global environment. He is also a recipient of the CIO 100 Award.
Most recently, Agnoli served as CIO of Reed Smith, an international law firm, where he oversaw global IT strategy, enterprise system operations, process improvement, and the development of new technologies. Prior to Reed Smith, he was Global IT Transformation Leader at Milan Pharmaceuticals (now Viatris) and CIO at the large law firm K&L Gates.
In 2024, Agnoli left Reed Smith to establish ‘SWA Executive Consulting.’ His goal is to help clients improve performance by leveraging his executive and technology leadership experience. He provides fractional CIO services and conducts diagnostics of IT strategy, infrastructure, and cybersecurity approaches.
Describing himself as “semi-retired,” Agnoli is also a senior instructor at Carnegie Mellon University’s ‘CIDO Executive Program,’ which helps technology and business executives develop into effective leaders.
“I’m focused on leveraging the 40+ years of experience and lessons learned in the IT and business world to help organizations improve their digital and IT capabilities, make processes more flexible and agile, and ensure business value from technology investments,” Agnoli stated.
Mentoring the next generation of IT leaders through his role at CMU is also a key focus. “I find meaning in translating my experience into something that is truly useful for people building their careers now,” he added.
Agnoli’s advice to late-career CIOs is clear: assess what you’ve done, focus on your strengths, differentiators, value proposition, and what you enjoy most. “Structure it so that capability can be used to help someone, and be valuable to you,” he said, emphasizing that “time is short. Don’t spend it on things you don’t enjoy, focus on what is most valuable to others and most enjoyable to you.”
“There’s Always a Principle That Holds”: Navigating to an Advisory Role
Lisa Rogers is a senior executive with extensive experience in leadership, business transformation, and IT strategy development. She is currently Vice President and CIO of Modern Technology Solutions, an engineering services and technology company, and anticipates this will be her last full-time role. Previously, she served as CIO for Oteemo, a technology solutions firm, and Dewberry, a construction engineering company.
“This role is challenging enough to keep me learning and engaged for the next 3-4 years,” Rogers said. “Transitioning from full-time employment to full retirement requires a transition period. The key challenges during this transition are managing taxes, securing affordable healthcare, and, most importantly, ensuring income stability during the early retirement phase.”
During the career transition, Rogers plans to serve on corporate boards as an independent director and participate in advisory committees related to workforce development. “The challenge is similar to landing your first C-level role: securing a ‘first seat’ as a paid independent board member,” she said. “Typically, this involves quarterly in-person board meetings, preceded by weeks of document review, preparation, and leadership/mentorship questions at the board level.”
Rogers believes that serving on 1-2 boards could provide financial stability without the demands of a full-time job. Like other late-career CIOs, she experienced age bias. “There was a clear age bias among some of the major universities when I started looking at the consulting world in a semi-retired state,” Rogers said. Potential employers questioned whether someone of her age could still contribute new and innovative ideas. Rogers emphasized that for late-career CIOs seeking new opportunities, the key selling point is not years of IT management experience, but demonstrated leadership, strategic planning, and vision.
Consistently exceeding expectations and achieving goals helped demonstrate competence and build trust. Understanding how the organization functions and aligning with key stakeholders was also crucial. Consistent networking contributed to strengthening professional connections, gaining insights, and opening new opportunities.
The most important principle is “treating people well.” Rogers said, “People and opportunities are drawn to those who are positive and kind. You will fall down, and when you do, someone will be there to help you up. They will be a shield when you need it.”
Technology and the workplace have changed rapidly, but core principles remain constant. “These principles have always been valid and have helped me stay competitive and achieve results in a constantly changing industry. By continuing to adapt and apply these principles, I’ve been able to grow and find fulfillment throughout various stages of my career,” Rogers stated. She advises those seeking board positions to not delay until retirement. “There’s a concept of the ‘72-year-old rule’ still prevalent – the expectation that board members will retire at 72. The optimal time to start looking for board roles is in your late 50s.” She also recommends investing in preparation, citing the National Association of Corporate Directors (NACD) as a resource for comprehensive education programs to prepare individuals for board service.
Taking the ‘Interim’ CIO Route
Another path for late-career CIOs is to take on ‘interim’ technology leadership roles. Bruce Tagert chose this strategy, taking a break to travel after about 26 years as a CIO before returning to work as a ‘replacement’ technology executive at Oregon State University and Juniata College.
Tagert currently serves as Interim Vice President and CIO at Worcester State University and also chairs the board of directors for the Pennsylvania Research and Education Network (KeystoneREN). Before becoming an interim CIO, Tagert spent approximately 20 years as a technology leader at Lehigh University, serving as Vice President of Library and Technology Services. He had overall responsibility for campus libraries, faculty development, academic and research information technology, administrative enterprise systems, and graduate remote education programs. Prior to Lehigh, he held an IT executive position at Portland State University.
Tagert believes the role of CIO has evolved during his career from a “technical expert” to a “strategic leader and planner.” He explained, “The key to growth and development is not the latest technology, but organizational development, IT workforce management, connecting with university leadership and the university’s strategic plan, and reading where higher education is going.”
He also experienced age bias. “When I came back from semi-retirement and started looking at the higher education CIO consulting world, there was a definite age bias among some of the major universities,” Tagert said. Potential employers questioned whether someone of his age could still make new and innovative contributions. Tagert advises late-career CIOs seeking new opportunities to emphasize leadership, strategic planning, and vision-setting abilities, rather than years of IT management experience.
