Today’s guest is Greg Caplan, Co-Founder of Dovetail, the IT managed service provider trusted by leading agencies including Uncommon, Quiet Storm and Isobel.

Greg brings a rare perspective on how technology is quietly reshaping the agency business model from the inside out. With a background in post-production and years spent supporting creative companies, he explains why IT is no longer a back-office function but a strategic driver of growth, resilience and client trust.

The conversation explores how agencies are navigating an increasingly complex landscape of cyber security, compliance requirements and distributed freelance teams. Greg also unpacks the rising importance of technology in new-business, where issues such as data governance and information security are now central to winning major pitches.

AI inevitably also features. Greg shares a pragmatic view of how agencies should approach it, from identifying ‘shadow AI’ inside organisations to building leadership-level understanding of the tools reshaping client relationships.

HIGHLIGHTS:

[04:29] The technology behind agencies

[06:19] AI strategy

[09:10] Automation powering freelancers

[12:28] Smart cyber strategy planning

[15:47] Confidentiality, integrity and accessibility

[20:04] Rooting out ‘shadow AI’

[25:01] Readiness for leaders

[27:19] The rise of specialised AI

[29:35] Liberating creativity