Truly SMB Execs on CEO Transition and SMB AI Needs

UK-based provider Truly SMB recently announced its co-founder, Vicky Critchley, has transitioned from CEO into a new role focused on long-term strategy. We spoke with Critchley and newly-appointed CEO, Tim Rookes, about the move and how the business serves SMBs looking for support along their AI journeys.

Truly SMB restructures leadership to advance long-term AI strategy

Critchley now serves as executive chair, as Rookes took the helm of day-to-day operations in early November. To her, the change is an opportunity to drive strategic initiatives and focus on big-picture planning without sacrificing the business’s operational needs today.

“This is an intentional plan that represents where we are in our journey,” Critchley said. “The goal with this is to split the day-to-day activities from the strategy and planning so we can do both equally.”

Rookes was the chief experience officer at Truly SMB before his appointment as CEO.

“It’s really exciting to take that plan and make it a reality,” Rookes said. “While Vicky’s working on where we’re headed, I can focus on our team and our customers. It’s unique to have someone like Vicky available to do this in this way, and it’s great for us.”

Rookes says his priorities as a leader are largely to continue the early momentum that Truly SMB has established, and for him, that starts with the internal team.

“I’ve always been a big believer in the fact that if you build a really good team, and they are happy and believe in what they do, that attitude extends to how they interact with customers, and then those customers are also more satisfied with their experience as a result,” Rookes said.

Inside Truly SMB’s service model for AI and IT modernization

Truly SMB specializes in AI technology and is a committed Microsoft partner. The company offers a variety of IT services and business solutions with the ultimate goal of supporting SMBs in the UK and other regions as they leverage AI in their operations.

Those offerings are broken down into three main categories, including:

• Business Solutions: The offerings cover accounting, sales, ERP, and productivity tools, all fixed price and built for the modern SMB.  
• IT Support Services: The company touts itself as a trusted tech partner, supporting clients with a variety of technology needs tied to business goals and outcomes. 
• Data and AI Services: Truly SMB helps clients automate processes and gain smarter insights with Microsoft Copilot and Power Platform.

“I’ve been in this industry for a long time. In the past, it’s been a lot of us as providers pushing technology onto people and having to explain why it’s good for their businesses and why it should be a priority for them,” Critchley said. “AI, though, is really a customer-first conversation in some ways. Most SMBs know they want to use AI, they just don’t know how to get started.”

Critchley says the speed at which AI innovations are coming to market, coupled with customer buy-in and interest in those tools, is creating a faster decision cycle than she has seen with other technologies. Still, customers don’t have all the answers to their questions, and that’s where providers like Truly SMB see a massive opportunity in front of them.

“They don’t know what they don’t know, ultimately,” Rookes said. “We don’t go in first with a technical conversation. Instead, we talk about what AI could do for the business generally, and then incrementally bring the technology. The security and data elements are a given for us, and we’ll absolutely address them, but we care more about getting these businesses to consider what’s possible.”

Growth plans through expansion, partnerships, and continued learning

Critchley told Channel Insider earlier this year about why she created Truly SMB specifically to support AI adoption. Now, after months of supporting the over 300 clients the provider already has, she remains committed to that mission.

Much of the next phase of growth, Critchley told Channel Insider, will be built on a three-prong strategy: organic growth, acquisition strategies, and partnerships with other organizations. For example, Truly SMB is working with various local government agencies to ultimately enable more businesses with AI.

As Rookes highlights, the company is also learning about AI as it goes, ensuring it stays ahead of the curve as much as possible.

“This is new to all of us as well, and we need to do the same things we’re helping our customers do,” he said. “We put ourselves on our own programs and send people out to events to learn about the technology. We also learn about it through using it the way we encourage our customers to.”