Recently, a group of senior IT leaders got together in central London to discuss the current squeeze that seems to be put upon the retail industry’s digital infrastructure, and their role in particular. So poignant was the topic that many described their predicament as being between a rock and a hard place, as the old adage goes (the rock being internal pressures from those who don’t understand the nuances of IT infrastructure, the hard place being strained relationships with suppliers).

Over the course of several hours, what emerged was a rare, candid look at the day-to-day pressures facing retail IT leaders and particularly, their increasingly fraught relationship with service providers.

Across the room, one theme dominated. That being a deep, almost visceral distrust of network providers. Not a single attendee could recall a recent moment when they had felt ‘truly supported’ by their provider. Instead, the mood was defined by tales of frustration, missed expectations and a sense that retail, as an industry, is treated as a low-tier priority by the major telecoms.

Martin Saunders, COO at Highlight, said the sheer strength of feeling was striking: “I don’t remember a single positive thing being said about anyone’s experience of service providers. The level of distrust in the industry currently is extraordinary.”

IT leaders’ ‘rock and a hard place’

For many in the room, large providers were painted as monopolistic forces. Impossible to avoid, yet uninterested in retail’s needs. One attendee quipped that fixing a retailer’s issue might cost a large provider “pennies,” but leaving it unresolved is cripplingly expensive for a smaller retail business.

Craig Smith, technical account manager at Highlight, noted that expectations and reality were miles apart: “Some of the retailers in the room had hundreds of sites. Others only one or two, but they all felt they should have the same level of priority from their provider. The problem is they expect a gold-standard service, but often are constricted by the cheapest contract available. When the reality doesn’t match, that frustration spills over.”

This commoditisation of connectivity was a recurring sore point. Cost-conscious tenders usually focus on price over quality, with little room for deeper conversations about service levels. Saunders reflected: “Very rarely does it get to the point of discussion about service quality, or about the ongoing relationship between customer and provider. What happens instead is a race to the bottom on price and when that happens, the human element, the actual support, is the first thing to be stripped out.”

The unseen and often unloved IT team

Another striking theme was the position of IT within retail businesses themselves. More than one attendee joked about being ‘hated’ within their organisations. One veteran even remarked she’d been disliked ‘for 30 years,’ the span of her entire career.

IT leaders often feel their departments are expected to be invisible. Fixing problems instantly, then disappearing. When things work, their efforts go unnoticed; when they don’t, the backlash is immediate.

Yet there are signs of progress. Several attendees noted that IT has become more embedded in projects over the last decade, with teams brought in earlier and seen as partners rather than back-office fixers. An IT lead explained that her team is now ‘in everyone’s business,’ and while that has been challenging, it has also delivered results. “People understand they need to loop IT in at an early stage,” she said. “The more information we have, the better and faster we can solve problems.”

Saunders argued that IT teams need to take greater responsibility for their own reputation within businesses: “Frankly, IT don’t do a particularly great job of fighting their corner internally. They don’t sell their importance, or PR themselves effectively. The challenge now is to show their value not just at board level but to the teams on the ground.”

Stuck in a jigsaw of providers

When asked why they attended the session, many retailers said they wanted to ‘sense check’ whether others were struggling as much as they were with suppliers and providers. The consensus was clear, everyone was.

In an attempt to cut costs, most IT leaders have assembled a patchwork of providers, but that mosaic of contracts makes accountability almost impossible. If something goes wrong, suppliers point fingers at one another, leaving in-house IT teams to chase down solutions.

“There’s a lack of agility or willingness to get under the skin of problems,” said one attendee. “You end up lobbed back and forth between provider and end user.”

The result is a cycle of wasted time and spiralling frustration. For some, the problem is so acute that new stores are being opened on 5G connections simply because promised infrastructure never arrives in time.

Expectations versus reality

Both Saunders and Smith pointed to a disconnect between what retailers think they are buying and the reality of what service providers deliver.

Smith explained: “Many IT leads compare their business broadband to their home broadband. At home, they have full control, and if it slows down, they only impact themselves. In a business environment, you’re trying to run critical systems for dozens of stores on the same type of service. That gap in expectation versus reality is where so much of the frustration lies.”

This mismatch is amplified by inflexible contracts. Retailers locked into 36-month agreements often find themselves trapped with services that no longer meet their needs, with penalties for change that can double costs. “There is definitely advantage-taking going on,” Saunders admitted.

Fixing the trust gap

While the frustrations are real, the roundtable also unearthed potential paths forward. One idea that resonated strongly was empowering store or branch managers with basic diagnostic tools. Instead of raising vague tickets, “it’s not working”,  they could follow a simple checklist before escalating issues. Highlight’s own tools were cited as a way to support this process.

Saunders explained: “We talked about giving non-technical staff a five-step list: check this, try that, then raise a ticket with this information included. That way, IT aren’t just receiving a blank complaint, they’re receiving something they can act on quickly.”

There was also recognition that IT needs to move beyond a ‘just fix it’ mindset and articulate how their work drives commercial outcomes. In a climate where retail margins are thin and investment in tech is constrained, IT’s role in protecting revenue and efficiency must be visible.

As one attendee summed up: “Historically, IT didn’t have to care about the bottom line. That’s changed. Now we need to show, in tangible ways, how we add value.”

A call for change

If one thing was clear from the roundtable, it’s that the relationship between retailers and service providers is broken. Retailers feel let down, stuck with contracts and systems that don’t deliver, while providers feel customers demand champagne service on beer budgets. Somewhere in the middle lies an opportunity for dialogue, better expectation-setting, and a renewed focus on outcomes rather than just costs.

As Saunders put it: “It’s rare you ever get someone coming to you with a list of problems and where their organisation is going in the future. When it does happen, it’s refreshing. Because then you can design something creative, something that really works. That’s the conversation the industry needs to have more often.”

Until then, IT leaders in retail remain wedged between demanding internal teams and service providers they don’t trust. This, really, is the very definition of being stuck between a rock and a hard place.

To discover more about Highlight or get in touch, click the link here.

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