While a lot of persona analysis is often informed by solid enough data, I reckon a good proportion of the insight is predicated on well-worn cliches – ‘cost sensitive’, ‘uptime-obsessed’, ‘risk-averse’, and ‘allergic to change’ are all likely to appear on the bingo card.
This got me thinking. How often are we actually going to source? So, I recently decided to do just that by interrogating an old mate, an IT Director at a large-scale B2B company, who preferred to remain anonymous for this piece.
He started off as a software engineer, subsequently taking on a team management role, before eventually ascending to his current senior position. Interestingly, he’s now spent nearly a decade in the same industry, creating strong domain expertise – he’s not just an IT practitioner, but someone who deeply understands how his remit impacts broader business development.
Outside work, he travels extensively, has an encyclopaedic knowledge of film, and keeps tabs on the worlds of football and professional wrestling. During the recent World Cup, when a group of friends were collecting Panini stickers, he built an app to streamline the process of trading. Gone are the days of manually swapping on the playground.
The test for deciding on whether to in-house or outsource
If you ask most IT vendors what they think an IT Director is weighing up, many will say cost. The actual decision-making criteria is far more nuanced: “Is this thing core to our unique value proposition? If it isn't, outsource it – the maths on cost almost doesn't matter.”
He went on to give me two examples. At a previous company, four developers were tied up maintaining an in-house HR system. His view was characteristically blunt: "That's not our USP – we’re a lab-testing company." He moved that effort onto a customer-facing app instead, which reinforced their differentiation, and pushed the original project out to a capable external vendor.
In another instance, his employer was running a bespoke in-house health and safety alert system rather than paying (low) five figures a year for a third-party one. On paper, the dev team felt ‘free’ given they were already on the payroll, a sunk cost with no marginal spend involved. But he considered that to be a false economy. The external option looked expensive next to a team that appeared to cost nothing, but it didn’t account for the fact that "you never can walk away from a system" once you've built it yourselves. It needs to be maintained across its lifetime, or it falls into disrepair.
Recruiting difficulty is a buying signal that marketers rarely mention
The other half of his framework considers whether you can, or should, staff the thing. His example was a 24-hour security operation, which gets outsourced not because it's cheap or unimportant, but because round-the-clock specialist cover often sits idle for his company: "I might only have an issue once every couple of months."
He described his team like a football squad – easy to find and keep burly defenders and midfielders, but hard to justify carrying a specialist playmaker that you rarely need, and this is what goes external.
His risk tolerance flexes with how close something sits to the core of the business. He's happy to pilot small, unproven vendors on peripheral problems, but for anything integral, he wants maturity and market weight – for instance, Microsoft Dynamics over a smaller, arguably better-fit competitor.
Even then, for a critical-incident vendor like his security provider, he deliberately chose one with a regional office over a bigger global name, because if it ever goes seriously wrong, he wants someone who can be on-site fast, not "a 12-hour plane ride away."
He's ultimately judged on three things
He broke down his own KPIs into three buckets:
- Run – keep the lights on.
- Integrate – joining up systems so acquisitions can create value.
- Transform – the part he enjoys most, including this year's AI targets.
The weighting shifts massively by company. He mentioned once interviewing at a manufacturing business where transformation barely featured, versus his current role where it's a major part of how he's evaluated. The upshot is that if you pitch innovation to someone being scored on uptime, your targeting strategy is all wrong.
The thing that gets you permanently blocked
I also spent some time talking with him about his dis/likes when it comes to vendor outreach. He told me about a recent cold call to his personal mobile while he was with family at a safari park. “That’s an instant, permanent block – not just of the call, but of the company, forever.” In a similar vein, a colleague of his, in HR, was cold-called on her personal number by an apprenticeship-sales firm. His perspective is clear: “It’s invasive and makes me immediately disqualify the vendor, regardless of how good the product might be.”
Generic AI-generated outreach is another Room 101 item. Pitching him commodity stuff that he's already got covered just comes across as completely irrelevant, while pure brand marketing with no technical substance has "very little" influence on him.
What actually works is a lot less glamorous than most go-to-market strategies often assume. Technical talks and peer conversations at events are important to him, because he can watch someone present live and tell whether they know their stuff or are, in his artistic words, "chatting bollocks."
Customer advocates with no obvious stake in the outcome are important as well. His best anecdote was being pointed, during a vendor talk, to existing customers in the audience and going to speak with them afterwards. That peer validation, from people with no skin in the game, is the vital gate before he'll meaningfully engage further.
He also pointed out that diligence scales with cost. Six figures, and he won't countenance spending a penny without a genuine reference call. Five to ten grand, and it’ll be a cursory glance under the bonnet.
The buying process has a mandate stage that most of us skip past
The lead time to closing a deal can be long and arduous, but there’s an early-stage gate to pass that can put the mockers on things from the outset.
“Does any budget holder in the business actually back this and do they think it’s worth spending money on?” No sponsor, no project, irrespective of the quality of the pitch. Legal and procurement only really show up once it’s down to a couple of finalists. This is where legwork has to be done by brands to enable advocates and champions to sell the case internally.
What’s more, when he is sourcing in an unfamiliar category, his first move is peer networks, online research, and events, well ahead of going near a vendor directly. In a boon for brand marketers, it was also interesting to hear that he prefers to raise his hand once ready – the implication being that vendors need to focus on appearing in the right channels while he’s mulling over his options.
So, what did I learn?
Selling to a senior IT person isn’t simply a rational features-and-cost comparison. They’ll be thinking about what’s critical to keep inside the business and when it makes sense to outsource, all while weighing up risk, judging a vendor’s credibility, and assessing whether there’s a critical mass of support within the business to justify a continued conversation.
Perhaps soberingly for some marketers, certain key personas appear to be unmoved by surface-level, glossy communications. They prefer to weigh up a vendor proposition at events, while also layering in assessments from peer and analyst networks. Failing that, you might as well see if you’ve got any World Cup stickers that the prospect still needs to complete his collection.
