The Virtual Hug of Service Delivery: Aaron Lake on 17 Years with Imagine Now IT
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Welcome to Ctrl-Alt-Deliver: MSP Service Delivery Mastery.
I’m Jeni Clift, joined by my husband and longtime business partner, Nick. Together, we’ve spent nearly 30 years building, scaling, and eventually exiting our own MSP business.
Over the years, we learned that real success in the MSP world isn’t just about the technology you deliver — it’s about how you deliver it. Building accountable teams, creating consistent client experiences, and knowing when to adapt your model are what keep clients loyal and your business sustainable.
In this episode, we sit down with Aaron Lake, General Manager of Imagine Now IT. Aaron’s been with the company for almost 17 years, starting his tech journey in a small computer shop back in 2003 before helping shape Imagine Now IT into the service-driven MSP it is today. Along the way, he’s built teams, developed client relationships, and formed a leadership style that puts empathy and listening at the heart of service delivery.
Here’s what we covered together:
✅ Why Aaron calls empathy in MSPs a “virtual hug” — and why listening matters even more than fixing the problem fast
✅ The art of teaching without “driving the mouse” — and how patience builds stronger teams and more confident clients
✅ The future of automation — what “agent-to-agent” systems could mean for MSPs, and why the human element will always be essential
✅ A practical look at balancing SLAs and client satisfaction without burning out your team
✅ What Aaron would do differently if he were starting an MSP today — and the lessons learned from nearly two decades in the trenches
We created this podcast to share the conversations we wish we’d had more of while running our own MSP — real, practical advice from people who’ve lived the challenges and come out stronger.
Whether you’re helping a stressed-out client, training your next superstar tech, or wondering how automation will change your role, this episode with Aaron is packed with insights you won’t want to miss.
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