Is it ever too late to reinvent your career?
In this episode of Tech Paired, Michael Phair is joined by Gerry Thomas, an experienced IT leader whose career journey proves that where you start does not have to define where you end up.
After spending 15 years in retail management, Gerry made the decision to return to education, retrain in technology, and build a career that would eventually see him leading enterprise-scale IT teams, managing major technology services, and supporting more than 20,000 users globally.
This is a conversation about career reinvention, resilience, leadership, enterprise technology, Microsoft governance, AI adoption, and the value of transferable skills.
Gerry shares how his early career in retail gave him the foundations that would later become critical in technology leadership: customer service, operational discipline, people management, commercial awareness, and the ability to work under pressure.
He explains why those 15 years were not wasted, but became the foundation for his success in IT.
We talk about the decision to go back to education later in life, what it felt like to sit in a classroom as a mature student, and how Gerry balanced family life, finances, self-doubt, and the challenge of starting again.
A major theme of the episode is mindset. Gerry explains why age became an advantage rather than a barrier, how maturity helped him approach learning differently, and why his first helpdesk role became more than just a starting point it became an opportunity to understand business systems, users, and the wider role of IT inside an organisation.
We also explore Gerry’s progression from first-line support into leadership, including the importance of taking ownership, volunteering for difficult work, asking for opportunities, and solving bigger business problems rather than just bigger technical problems.
From there, the conversation moves into the reality of enterprise-scale IT. Gerry shares what it is really like to support technology services for tens of thousands of users, why assumptions can be dangerous during incidents, and why facts, governance, communication, and impact awareness are critical at scale.
We also dig into Microsoft licensing, Copilot, AI governance, and automation. Gerry explains where organisations commonly waste money, why SharePoint storage and consumption-based charging can quickly get out of control, and why AI without proper governance can become expensive risk.
He shares a practical view of Copilot adoption, including the importance of data governance, permissions hygiene, sensitivity labels, user education, adoption metrics, and clear controls before scaling AI across an organisation.
Finally, Gerry gives honest advice to anyone wondering whether it is too late to change career. His message is clear: do not wait for someone to hand you the opportunity. Take ownership, keep learning, manage your risk, and use the experience you already have as an advantage.
This is a practical, honest, and inspiring conversation for anyone thinking about changing career, moving into technology, leading IT teams, scaling enterprise systems, or understanding how AI and governance are reshaping modern organisations.
In this episode, we cover:
• Reinventing your career later in life
• Moving from retail into technology
• Why transferable skills matter
• Going back to education as a mature student
• Starting again in a first-line helpdesk role
• Building confidence in a new industry
• Career progression through ownership and persistence
• Moving from technician to IT leader
• Managing technology services for 20,000+ users
• Enterprise IT pressure, incidents, and impact
• Why facts matter more than assumptions
• Microsoft licensing waste and optimisation
• SharePoint storage and consumption-based charging
• Copilot rollout reality versus hype
• AI governance, data controls, and permissions hygiene
• Why “AI without governance is expensive risk”
• Automating joiners, movers, and leavers
• Advice for anyone wondering if it is too late to change career
Tech Paired is the podcast from Tech Pair, exploring the people, careers, teams, and technology shaping the future of work.