Choosing an IT support partner is one of the most consequential operational decisions a hospitality business makes. It sits quietly under almost every shift you’ll ever run - payments, bookings, kitchen tickets, rotas, stock, guest WiFi, the lot - and yet most operators pick on price or gut feel. I’ve sat opposite enough finance directors and ops directors over the years to know how the conversation usually goes: three quotes, a friend’s recommendation, the cheapest one wins, and then twelve months later we’re being asked to come and clean it up.

This is the framework I’d use if I were buying IT support for a hospitality group tomorrow. It’s not academic. It’s the questions I’d want answered before I signed anything, and the red flags I’d run from.

Start with the filter: generalist MSP or hospitality specialist?

Before you even shortlist, decide which pond you’re fishing in. Most managed service providers (MSPs) in the UK support a generalist book - accountants, law firms, charities, the odd manufacturer. They’re often very good at what they do. But hospitality is its own animal, and the gap between “we support businesses” and “we support hospitality businesses” is much wider than it looks on a website.

Here’s what a hospitality specialist understands without needing it explained:

  • EPOS platforms (Oracle Micros, Zonal, Tevalis, Lightspeed, Toast, TISSL and the rest), how they integrate with kitchen display systems, and what breaks when an integration goes down mid-service
  • Tronc and payroll feeds out of the till
  • Hotel PMS environments and the channel manager / OTA stack sitting behind them
  • Guest WiFi as a distinct discipline from staff WiFi, with its own captive portal, marketing capture and compliance considerations
  • PCI DSS - what scope your card flow actually puts you in, and how to keep it as small as possible
  • Seven-day trading and the trading calendar. Christmas, Valentine’s, the May bank holidays, Pride, the Six Nations, the Saturday before Mother’s Day. These are the days you cannot afford a P1 ticket sitting in a queue
  • Site openings on a fixed lease date with no slippage allowed

A generalist MSP can learn all of this. Some do, eventually. But you don’t want to be the customer they’re learning on. For more on what a hospitality-first support model looks like in practice, see our hospitality IT support page.

The ten questions to ask every candidate

When you get to shortlist conversations, these are the ten questions I’d put on the table. The answers matter less than how comfortable the person across the table is giving them.

1. What percentage of your customers are hospitality or restaurant groups?

You’re looking for a real number, not “a lot” or “we have several”. If it’s under about 30%, you are not their core market. That’s not automatically disqualifying, but it tells you where their investment, tooling and on-call rotas are pointed.

2. What’s your SLA for “payment terminal down” outside 9 to 5?

This is the killer question. A lot of MSPs have a beautiful SLA matrix that quietly applies only between 9am and 5pm, Monday to Friday. Ask them specifically: it’s 8pm on a Saturday, the card terminals at one of my sites have stopped taking payment, what happens, and in what timeframe? If the answer involves a voicemail and a call-back on Monday, walk away.

3. Who actually supports us on a Saturday night?

Related but distinct. Is it the same engineers who answer the phone on a Tuesday morning, or is it an outsourced overnight desk in a different country reading from a script? Neither is wrong by definition, but you need to know what you’re buying, and you need them to be honest about it.

4. What EPOS platforms do you support in-house, and which do you refer on?

No MSP supports every till system to the same depth. A good answer is specific: “We do Zonal and Tevalis end-to-end, we co-manage Oracle Micros with the vendor, and we don’t touch Toast.” A bad answer is “we support all of them”. They don’t.

5. How do you handle new site openings?

Ask them to walk you through their last NSO. How many weeks out did they get involved, who from their team was on site for the soft launch, what went wrong and what did they do about it. You’re listening for project management discipline and a story they’ve clearly told before.

6. What does your onboarding process look like?

The first 90 days set the tone for the entire relationship. You want to hear about discovery, documentation, an asset register, password vault migration, monitoring deployment and a named transition lead. If onboarding is “we’ll get the tickets and crack on”, that’s a problem.

7. How do you charge - fixed per user, fixed per site, or pay-as-you-go?

There’s no single right answer, but you need to understand the commercial model and how it scales as you open more sites. Pay-as-you-go can look cheap at month one and ruinous in month nine. Fixed-per-site is usually the cleanest for hospitality. Our own approach is laid out on the pricing page - have a look and use it as a benchmark when you’re comparing quotes.

8. Who are your three most similar customers, and can I speak to them?

If they hesitate, that’s your answer. Any specialist worth hiring will have a list of references they can put you in touch with the same day. Ring them. Ask the references what’s gone wrong, not just what’s gone right - every relationship has friction, and you want to know what theirs looks like.

9. Are you independent or investor-owned?

This isn’t a moral question. There are excellent private-equity-backed MSPs and there are mediocre independents. But the ownership model tells you something about the pressure the account team is under and where decisions are made. PE-owned MSPs are often in a roll-up cycle where the priority is integration and margin expansion, which can show up as account managers being replaced and service desks being consolidated abroad. Ask, and listen for what they don’t say.

10. What certifications do you hold that matter for us?

Cyber Essentials and Cyber Essentials Plus are table stakes. Microsoft Solutions Partner status (and which designations) tells you whether they’re current on the Microsoft 365 stack you almost certainly run. PCI DSS qualifications matter if you’re going to ask them to help with scope. ISO 27001 is nice to have. If they can’t produce certificates on request, they don’t have them.

Red flags

After enough of these conversations you start to recognise the warning signs. The ones I take most seriously:

  • Vague answers to specific questions. “It depends” is fine if it’s followed by “and here’s what it depends on”. On its own it’s a stall.
  • No hospitality references they’re willing to name.
  • A service desk that goes home at 5pm with a duty phone hanging off the back of it.
  • Account management that only ever wants to talk about renewal and upsell, never about the operational stuff that’s actually breaking.
  • A sales process that never includes a technical person from their side.
  • Slide decks heavy on logos and light on numbers.

Green flags

The opposite is just as recognisable:

  • Specific, confident answers, including “no, we don’t do that”.
  • Named expertise on the EPOS and PMS platforms you actually run.
  • Hospitality references they’re proud of, including ones you’ve heard of.
  • A clearly published SLA for service-time incidents, not just business hours.
  • A technical lead who turns up to the second meeting and asks better questions than the salesperson.
  • A view on cyber security that goes beyond antivirus and into segmentation, identity, backups and incident response.

On the procurement process itself

A quick word on RFPs. I understand why finance teams love them. They feel rigorous, they create an audit trail, and they reduce the decision to a spreadsheet. But for IT support in hospitality, RFPs often get you the wrong answer. They reward providers who are good at writing RFP responses, which is a completely different skill from being good at fixing a card terminal at 8pm on a Saturday. They also flatten meaningful differences between providers into yes/no boxes, and they strip out the conversation where you’d find out whether you actually want to work with these people.

If you must run an RFP, keep it short, weight references and a site visit heavily, and make sure at least one stage is a face-to-face meeting between your ops director and their service delivery lead. If you don’t have to run an RFP, don’t. Have three proper conversations instead.

Contract terms - what to push on

When you get to paper, the contract matters more than people think. The clauses I’d pay attention to:

  • Term length. I’d push for a 12-month initial term with a rolling monthly contract after that. Three-year lock-ins are common and almost always benefit the supplier more than the customer. If you’re being offered a discount for a longer term, work out the maths and ask whether you’d rather have the flexibility.
  • Exit clauses. What happens to your data, your documentation and your password vault when the contract ends? You want a clean, contractual handover obligation, not goodwill.
  • Price review mechanism. Annual CPI-linked is reasonable. “At the supplier’s discretion” is not.
  • Scope creep. Be clear about what’s in the fixed fee and what’s billable. Ambiguity here is where relationships sour.
  • Sub-contracting. Are they allowed to pass your support to a third party without telling you? You probably want a notification clause at minimum.

How CloudMatters fits this framework

I’m not going to pretend this isn’t a sales piece - I’m the sales director, you knew that when you started reading. But the framework above is the framework I’d use whether I worked here or not, and it’s the one I’d want a customer to hold us to.

For what it’s worth, here’s how we map onto it. Around 90% of our customers are hospitality or restaurant groups. We have a 30-minute response SLA on payment-down incidents, 24/7, 365 days a year, answered by our own engineers in London. We support Oracle Micros, Zonal, Tevalis and Lightspeed in-house and are honest about the others. We’re independent, founder-led, and based in W1T 7NY because most of our customers are within a short walk. Cyber Essentials Plus, Microsoft Solutions Partner, and we’ll send you the certificates before you ask. You can read more about the team on the about us page.

If any of that sounds like the right fit, or if you just want a second opinion on the proposals you’re already looking at, get in touch via the hospitality IT support page. Bring the questions. We’ll bring the answers.