On this episode of The Smart IT Podcast, I welcomed Jared Webb to the show for an discussion on the future of IT operating models. We reflected on how different companies, even those of similar size and industry, approached IT strategy in unique ways, shaped by leadership style, risk appetite, and business goals.

We explored how many IT teams had shifted from building large in-house teams to adopting more agile, partner-driven models as technology cycles accelerated. Jared emphasized that IT leaders needed to first understand the business, balance risk, and work closely with stakeholders to identify efficiencies and create value.

We discussed the importance of trust between IT and business leaders, noting that far too many organizations struggled because executives made technology decisions without IT’s full input. IT should proactively bring forward improvement ideas, using clear storytelling to secure buy-in. He highlighted how strategic thinking was often undermined by the expectation for IT leaders to remain deeply tactical.

The conversation also explored vendor management and the critical role of value-added resellers and partners. Jared stressed the need for diligence, warning that outsourcing without oversight could lead to poor service. He described how trusted sales relationships often outweighed technology features in purchasing decisions.

We turned to development strategies, weighing in-house versus outsourced approaches. Jared noted that advances in AI had made small, skilled teams far more capable, shifting the balance toward building internally where possible. Still, he cautioned that businesses often undervalued experienced IT staff, leading to risks from “brain drain” and over-reliance on junior talent or quick fixes.

Finally, we examined broader cultural challenges: short-termism in business, the risk of ignoring institutional knowledge, and the need for IT to demonstrate value in long-term competitiveness. We agreed that trust, communication, and relationship-building were the cornerstones of effective IT leadership. IT leaders must pair technical expertise with strong human skills, preparing for a future where they may oversee both people and automated systems.

A much needed conversations in these uncertain times for everyone to review their operating model and adapt it as needed to maintain pace with their organizations growing needs.

Production: Brilliant Beam Media | Syya Yasotornrat

#SmartIT #IT #technology #operatingmodel #businessstrategy #vendorrelationships #riskmanagement #leadership

Show notes:

Link to episode: https://youtu.be/9uO8ceIWeOo

🔹Link to this episode: https://youtu.be/9uO8ceIWeOo

🔹Jared on LinkedIn: https://www.linkedin.com/in/jaredlwebb/

🔹The Smart IT Podcast YouTube Channel: https://www.youtube.com/@thesmartitpodcast

🔹Captivate Website for all episodes: https://the-smart-it-podcast.captivate.fm/