Cloud Direct has been helping organisations overcome the constraints of legacy IT for more than two decades. Founded in 2003 by Brett Raynes, the company began by providing managed backup services to support business continuity, before expanding its portfolio as customer needs shifted – through the rise of cloud computing and now into what CEO Leighton Searle describes as the era of agentic AI.
That sense of continuity alongside reinvention is central to Cloud Direct’s story. While company's ambitions and the tools it uses have changed dramatically since its early days, Searle is clear that the company’s founding principle has remained consistent: technology should unlock business value rather than create unnecessary complexity.
“2003 was a long time ago,” says Searle, reflecting on the company’s history. “The technology landscape was very different, and a big part of Brett’s vision was about solving the problem of backup. Our initial aim was to help organisations move to fully managed services for backup so they would have the freedom to innovate and scale.”
As cloud computing matured, Cloud Direct’s philosophy naturally extended into helping organisations modernise their infrastructure and escape the limitations of legacy systems. Today, however, that mission has broadened again.
“It’s not just about migrating to the cloud, it’s very much about modernising, securing and really transforming how organisations work,” says Searle. “Particularly now in what I refer to as the AI era, there is the potential to unlock so many possibilities from AI, through to fully automated operating models. It’s what I call the agent-ready enterprise.”
This evolution is being formalised through Cloud Direct’s refreshed strategy, which was launched company-wide at the start of 2026. Cloud Direct’s new mission, Searle explains, is centred on “empowering ambitious people and organisations through responsible AI and trusted technology to achieve the outcomes that matter”. The accompanying tagline – “human-led, AI-powered outcomes that matter” – is intended to capture the balance Cloud Direct is aiming for as it enters its next chapter.
A partnership built on depth and experience
Cloud Direct’s long-standing partnership with Microsoft is a key enabler of its ambition to help firms become agent-ready. For Searle, who previously spent nearly 20 years at Microsoft and served on Cloud Direct’s board prior to becoming CEO in December 2025, the relationship between the two partners is both deeply familiar and newly revealing.
“It’s a big part of the reason why I’m here,” he says. “I met Cloud Direct because I understood its importance to Microsoft. But it’s been really interesting sitting on the other side of the table for the last month or so.”
Cloud Direct is a Microsoft Azure Expert managed service provider and holds multiple Microsoft certifications, positioning it as both a strategic and operational partner. “We work hand in hand on things like new solution development, go-to-market and co-selling, and more recently on AI skilling,” explains Searle.
The emphasis on skills development reflects a broader shift in how Microsoft engages with its partner ecosystem, particularly in the mid-market. “From the Microsoft lens, I can understand how important partners are – most customers experience Microsoft through partners like Cloud Direct,” says Searle. “The skilling piece has been a real shift lately.”
Searle points to events such as FabCon (the Microsoft Fabric Community Conference in Atlanta, Georgia, USA) and upcoming AI-focused initiatives as examples showcasing how closely partners are connected to Microsoft’s engineering teams. “Microsoft brings the whole Fabric engineering team across, so partners like Cloud Direct get direct access to these experts for skilling and learning,” he says. “At the pace we’re moving in technology as an industry, it’s super important Microsoft’s partners can leverage AI.”
Preparing organisations for agentic AI
Beyond enablement, the partnership increasingly centres on co-building future capabilities, particularly in AI and security.
Cloud Direct takes a strategic approach to AI, helping organisations navigate adoption in a way that delivers tangible business value. Searle emphasises that the company’s expertise goes well beyond simple infrastructure migrations.
“What we’re really aiming to do is prepare organisations to adopt agentic AI, and do that in a way which is secure, responsible and with business outcomes in mind,” he says. “That ‘outcomes that matter’ part of our mission is really important. The challenge is that the capability of AI far outweighs our ability to get value from it – because it’s really about organisational and business process change.”
A major differentiator of Cloud Direct’s work, he claims, is the depth of experience Cloud Direct has accumulated over two decades of operating Microsoft-based environments.
“We’ve migrated hundreds of customers to the cloud, run and operated their infrastructures right across the Microsoft technology portfolio,” he explains. “From this, we have developed a huge knowledge base of customer patterns. Every support call and deployment adds to our understanding.”
That institutional knowledge has been formalised into what the company now calls Cloud Direct IQ.
“Cloud Direct IQ is uniquely ours,” says Searle. “It means every team member, empowered with responsible AI, is grounded in that knowledge base of experience. And we can share that knowledge not only within our teams, but directly with our clients too.”
This intelligence underpins the company’s managed services platforms, which are increasingly infused with AI to reduce complexity and accelerate time to value for customers. Alongside this, Cloud Direct has embraced a strong customer zero mindset, using its own organisation as a proving ground for AI-enabled ways of working.
One visible outcome of this approach is Cloud Direct Studios, a new board-level consulting capability focused on AI and business impact. “This is about helping customers find the right use cases where they can get value really quickly,” says Searle. “We get organisations agent-ready from an infrastructure point of view, but we also want to help them build the organisational capability to take advantage of AI.”
Security as a foundational concern
Cloud Direct is sharpening its focus on cloud, data and AI modernisation; AI productivity; and security and compliance as core pillars for its customer service. As this happens, Searle is adamant that security must be treated as an integral, front-loaded consideration rather than an afterthought.
“Security isn’t a standalone thing anymore, but it’s also not a downstream consideration,” he says. “If you fast-forward to where we have autonomous AI agents operating across organisations, that introduces new security parameters and new kinds of risk.”
Those risks extend beyond traditional cyberthreats to include accidental data exposure, governance failures and reputational damage linked to AI use. “There’s a new frontier of security emerging as you introduce more AI, so it has to be designed upfront,” says Searle.
In keep with this philosophy, Cloud Direct has updated its own internal responsible AI policies and mandatory training programmes.
“One of the first things I’ve done is a review of our responsible AI policy,” says Searle. “We’ve included a responsible AI training course, which will be mandatory for everyone at Cloud Direct. Level one is all about responsible AI usage, how to work with and trust AI, and what our principles are.”
He points to Cloud Direct’s ‘intelligent resources’ function, which unites HR and development teams, as a standout example of the firm being its own customer zero. Leveraging this approach, Cloud Direct developed an internal AI agent to tackle a specific Microsoft licensing challenge and rapidly refined, secured and rolled it out company-wide, turning a targeted solution into a scalable capability.
Becoming frontier organisations
Cloud Direct’s approach of combining strategic AI planning, responsible governance and practical deployment feeds into its goal of helping customers become what Microsoft terms ‘frontier’ organisations.
“To be a frontier firm, you need to tackle problems and approach business processes with an AI-first mindset,” says Searle. “It’s not just about deploying Microsoft Copilot but also about rethinking processes to unlock the full potential of AI.”
He draws a comparison with organisations being founded today.
“If you were starting an organisation now, with all the AI technology that exists, you’d build a very different organisation than you would have five or ten years ago,” he says. “Those are real new competitors coming into every market.”
For Cloud Direct, becoming a frontier organisation involves moving from traditional organisational structures to a focus on how work actually gets done, supported by AI-enabled value creation systems. “It’s moving from the organisation chart to the work chart,” says Searle. “How does work get done, and how can AI fuel that work?”
This mindset is shaping the next generation of managed services Cloud Direct is developing. “The new services are about standardising AI adoption paths to ensure measurable outcomes,” says Searle. “We’re applying everything we know about managing identities, infrastructure and devices to agents, which are effectively semi-autonomous teammates.”
The services will focus heavily on improving AI governance, observability and confidence, and will address barriers that currently prevent organisations from moving AI into production at scale. “These are real problems our customers are facing,” notes Searle. “And with the new technology coming from Microsoft, we’re well positioned to run AI for our customers and operate that at scale.”
The next chapter will be human-led
As Cloud Direct enters this next phase under Searle’s leadership, he is keen to emphasise continuity as much as change. Searle sees his task as building on a strong cultural foundation.
“There’s an awesome culture here, one that is very customer-centric,” he says. “People really go the extra mile to solve customer problems. That’s what inspires me the most and those are the foundations I’m building on.”
Looking ahead, Searle hopes customers will see Cloud Direct as a partner capable of guiding them through profound technological change without losing sight of the human dimension of work.
“We have a world view that the future belongs to organisations that can embrace secure and scalable, agent-ready AI transformation in a way that preserves the unique human capabilities in that process,” he says. “Cloud Direct is a partner that will get them there safely, confidently, and at pace.”