There’s a paradox in the IT services advisory market that has been hitting me for years: the people tasked with advising companies on how to choose their technology vendors are, in the vast majority of cases, people who have never built, priced, delivered, or defended an IT service in front of an unhappy customer.
This isn’t a critique. It’s a structural observation. And it has real consequences on how sourcing decisions are made, and on how many of those decisions turn out to be wrong.
The job, seen from the inside #
I spent more than fifteen years on the other side of the table. Not as someone who evaluates IT services, but as someone who designs them, sells them, delivers them, and is accountable when something doesn’t work.
At YNAP (Yoox for the older folks) I saw how one of the largest European e-commerce platforms managed the relationship with its technology vendors. Not in theory: in the day-to-day practice of architectural choices, negotiations over deliverables, decisions that determine whether a project delivers value or delivers only code.
As CTO of Anthis I built from scratch the technical infrastructure and delivery processes of a company. It’s the kind of experience that teaches you that the difference between an IT service that works and one that doesn’t is almost never in the technology chosen, but in the quality of the decision-making process that leads to that technology.
And today, as Head of Tech & Partner at Oltrematica (I know, this role doesn’t exist but we’ll get there), I run a portfolio of projects for clients ranging from TIM to Randstad, from the Abruzzo Region to the Chambers of Commerce. I write RFPs and respond to RFPs. I define SLAs and I have to meet them. I price managed services knowing exactly how much each component of the delivery chain costs.
This experience gave me access to a kind of knowledge that is hard—maybe impossible—to acquire from the outside.
The things you can only see from the inside #
When I read provider evaluation frameworks (Magic Quadrant, PEAK Matrix, ISG Provider Lens) I recognize the quality of the analysis and the methodological rigor. But I also see the blind spots. And they’re always the same.
The real cost of an IT service isn’t in the price #
The quoted price in a managed services offer is a number. The real cost is a complex system that includes the price, plus the cost of communication inefficiencies, plus the cost of technical debt that accumulates when the provider cuts corners to stay within budget, plus the opportunity cost of features that don’t get delivered because the contract doesn’t include them.
An analyst who evaluates providers by comparing day rates is measuring the wrong variable. A provider that quotes €400/day and delivers in 20 days costs less than one that quotes €300/day and takes 40. But to understand which one will deliver in 20 and which in 40, you need to know how to read the proposed technical architecture, the team composition, the level of automation in delivery processes.
It’s a competence that comes from having built those processes, not from having observed them.
SLAs are a language, not just a contract #
In my experience, most problems in IT outsourcing contracts don’t come from wrong SLAs. They come from ambiguous SLAs.
An SLA that says “99.9% availability” is technically precise but operationally empty if it doesn’t specify: how is availability measured? Is scheduled maintenance included? What time window is used for the calculation? What happens when downtime is caused by a third party (the cloud provider, the CDN, the DNS)?
I’ve written SLAs for years. And I learned that a good SLA isn’t the one that promises more, but the one that defines with surgical precision what happens when things go bad. Because in IT services, things always go bad sooner or later. Provider quality is measured in the response, not in the promise.
Team composition matters more than size #
Evaluation frameworks tend to reward providers with large teams and multiple delivery centers. It’s a reassuring metric for buyers: more people = more capacity. But anyone who has managed development teams knows it’s not like that.
A team of 5 well-coordinated senior developers produces more high-quality output than a team of 15 people with 3 layers of management and constant turnover. Especially when that team of 5 uses AI-native methodologies that multiply individual productivity.
At Oltrematica we simultaneously run 8–10 active projects with a team of about 10 people. Not because we’re heroes, but because we invested in automation, efficient delivery processes, tools that eliminate low value-added work. It’s the kind of efficiency that doesn’t show up in any quadrant.
The value of an operational perspective in advisory #
I’m not suggesting that all analysts should have worked as IT providers. I’m suggesting that the operational perspective is a strategic asset in advisory that today is dramatically underrepresented.
When a CISO asks me whether a managed security provider is reliable, I don’t have to rely only on certifications and references. I can read the proposed architecture and understand whether it was designed to be operated or just to win the bid. I can look at the Statement of Work and identify the gray areas that will turn into contractual disputes 18 months from now. I can assess whether the proposed staffing model is sustainable or whether the provider is promising a team they don’t have and will have to build after-the-fact.
This kind of insight doesn’t come from analytical rigor. It comes from having lived the same dynamics on the other side. And it has enormous value for enterprise clients who are about to make multi-million-euro sourcing decisions.
The necessary convergence #
The IT services advisory market is entering a phase where the complexity of sourcing decisions is increasing exponentially. AI, European compliance, reshoring, new pricing models, cybersecurity by design: these are all dimensions that require deep technical understanding to be evaluated correctly.
Generic frameworks are no longer enough. Clients ask for—and have the right to get—advisors who speak the providers’ language with the same fluency with which they speak the language of business.
It’s a convergence that the market hasn’t produced systematically yet. But it’s inevitable. And whoever anticipates it will have an enormous competitive advantage.
This article is the first in a series on my view of the IT services sourcing market. In the next piece I’ll explore my personal journey—from developer to partner—and how each phase helped build an integrated perspective on the IT services market.