Retailers run on infrastructure, but the relationship with the managed service providers tasked with running that infrastructure and keeping stores connected is often far more fragile than it should be.

Each retailer, store or working location is an internet of things, which fundamentally have to speak to one another. Anecdotally, a QSR IT specialist told Retail Gazette recently that when Wi-Fi went down in a location last year, the dishwasher wouldn’t work anymore. Such is the essentiality of connectivity.

And yet, for something so fundamental, the relationship between retailers and their managed service providers, the people tasked with preventing failures as a preference, or fixing them as a last resort, is surprisingly brittle. That tension sat at the heart of a recent roundtable discussion hosted by Grocery Gazette and Highlight, a company that offers managed service observability to retailers and grocers.

For Peter Savereux, Head of Marketing at Highlight, the motivation was clear from the outset. “From previous roundtables and from general interactions we’ve had with customers of service providers over the years, it’s a crucial relationship, but it’s not always a successful one,” he said. “There’s often a constant cycle of churn, and long-running relationships are rarer than they are common.”

In this sector, where IT underpins every transaction, constant provider turnover is more than simply a minor inconvenience. It is a fundamental breakdown, and an admission of lost investment in a key relationship.

Security, unsurprisingly, loomed large over the conversation. Retail IT leaders are operating in a climate where no one wants to be the next headline. “It’s in their mind 100 per cent of the time,” Savereux observed. “Nobody wants to be the next reputation-damaging headline; this shop is shut down for days and data has been lost etc.”

Those in attendance noted that, when a data breach happened on the watch of their providers, very few were willing to own up to the error. “If you just told me truly what happened,” one retailer noted, “we could just move on. But I don’t like being gaslit”.

But security, for all its urgency, was not the sole root cause of dissatisfaction with MSP relationships in the room. What emerged instead was misalignment, poor definition, and a chronic failure to articulate what success actually looks like.

The retailers who described stronger, more resilient MSP relationships shared a common trait. They had done the hard work up front. “They were putting a lot of effort in on the front end,” Savereux explained. “They were able to define exactly what their challenges are, and what failure and success scenarios would actually look like.”

Retailers often approach MSPs because they lack specialist capability in-house. They know they need help. What they frequently cannot articulate is the commercial definition of ‘good’. Not just uptime percentages or response times, but what tangible improvement the business should feel at the end of the contract.

“You go to a service provider because you’re trying to solve a problem and you’ve determined it can’t be done in-house,” Savereux said. “But if you’re not able to say exactly what outcomes need to be enabled or what metrics would constitute a failed service, then both sides of the relationship are on to a losing game.”

Service providers are not blameless either. Too often the conversation narrows to technology procurement. “Sometimes a service provider will just take it as read: you’re asking me for XYZ technology. We can supply XYZ technology. But that’s only 25 per cent of the story.”

The remaining 75 per cent is harder and less tangible without the tools to prove the value of the service surrounding the technology. How will the solution be supported? How will success be measured beyond SLAs? How will capacity decisions be verified? Is the MSP genuinely contributing to business resilience and performance, or merely ticking contractual boxes?

“Communication is not necessarily just about talking,” Savereux noted. “It’s about having the tools and the data at hand to make sure everyone understands what’s working and what isn’t. If you can’t have a long-running relationship, you can’t really build that kind of trust very easily.” Longevity, in other words, is not just about contract length. It is about shared clarity.

Perhaps the most revealing moment of the roundtable, however, was not about technology or communication. It was about brand power.Savereux has long questioned why retail IT teams so often select large incumbent providers, even while privately criticising the lack of flexibility and attention they receive. “We’ve always wondered why IT leaders routinely go for the big guys who see them as small fish,” he said.

The answer lies beyond the IT function as one roundtable attendee noted. “The C-suite sees the brand power in the big guys. They think, ‘we’re a growing company, we need the ability to scale quickly. So, we need to go for the incumbent large companies because they have a recognisible brand.”

It is a rational instinct. Large logos signal safety. They reassure boards and investors, yet as Savereux acknowledged, IT leaders often know that scale on paper does not always translate to suitability in practice. “They know it’s not always the best solution because retail requires individual solutions and flexibility that the larger providers can’t deliver. But they need things signed off. They need budget approval. And without that brand power, they struggle to push smaller solutions internally.”

That internal tension is rarely discussed openly. But it may explain much of the churn. Interestingly, many of the retailers who reported stronger relationships were working with smaller, more agile MSPs. Providers able to flex as store estates expand or contract. Providers with tighter account management. Providers who can adapt to the unpredictable rhythm of retail trading.

“Networks sometimes grow and sometimes they shrink in retail,” Savereux said. “It’s just the nature of the game. Yet one of the issues that smaller MSPs have is that they are growing very well technically but marketing comes with growth at a later stage sometimes. They can solve the problems of retail customers but they don’t have the ability to sell themselves to those prospects effectively.”

If there was a single thread running through the discussion, it was this. Most failing MSP relationships are not undone by catastrophic technical incompetence. They unravel because expectations were never clearly aligned in the first place.

Retailers need to define outcomes in commercial, not purely technical, terms. MSPs need to probe deeper, communicate more transparently and demonstrate value beyond compliance with SLAs. And both sides need to recognise that trust is built through visibility and shared understanding, not logos or contract length.

“We probably had a suspicion that it was just service providers failing to meet the needs of their customers,” Savereux admitted. “But there are also challenges on the customer end that are making it difficult for service providers to know how to help.”

Perhaps the most important point revealed from the day is that both retail IT leaders and the service providers they engage with need to challenge each other as they define the services they’re going to buy and sell. IT leaders want expertise and pushback and they want communication that boosts the value of the services they’re buying, they need the business-level metrics and information that can justify their choices that might deviate from initial C-suite instincts to run to the large incumbents.

To this end, it’s important that the correct service observability, support and reporting mechanisms are in place and utilised effectively. Savereux closes the discussion, “After 20 years of supporting MSPs with unified observability and helping them to communicate with their customers, we at Highlight know you can only manage and talk about what all parties can see. Get that part right and you’ll have customer relationships that last years and not just one contract cycle.”

To find out more about Highlight, get in touch here.

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