Why the Best IT Leaders Are Financial Storytellers — Derrick Diaz, The Guardian US

Derrick Diaz spent a decade at Pinterest, joining as a systems administrator when the company had roughly 150 employees and leaving as it approached 8,500, having helped shape its global IT programme. A subsequent period at Citadel, an organisation that had deliberately optimised its size rather than its headcount, gave him a second and very different model of scale. 

Derrick Diaz now leads IT at The Guardian US, where the compliance and security standards that protect journalists sit alongside what he describes as a blank canvas for infrastructure. Over more than twenty years, he has become known for untangling organisations that grew faster than their systems, and for a conviction that the technical work is the easy part: the harder discipline is learning to communicate with executives in the way each of them listens.

What attracted you to a 200-year-old newspaper?

Derrick Diaz explains how the Guardian’s funding model creates startup conditions inside a two-century-old institution.

“I have been part of two very large companies, Pinterest and Citadel, and they are quite different. From a structural standpoint, the Guardian sits somewhere between the two. I think I was employee 150 or 160 at Pinterest, and by the time I left ten years later it was 8,500 people. Citadel had optimised its size and decided it would grow revenue rather than headcount.

The Guardian is a 200-year-old newspaper, so it builds incrementally, but it still functions in a very startup manner. It is supported by a mix of subscriptions, donorships, advertising and the Scott Trust, and everyone is constantly asking how much our dollars support the journalism. That forces people to wear multiple hats, which is exactly what it was like when I started at Pinterest. I realised I missed that.

There is red tape around ensuring the journalism, the security around the journalism and the compliance are held to a very high standard. In the environment we currently have in the United States, people are suing journalists, so data protection and legal hold protection have to be buttoned up. But from an infrastructure standpoint, it is a blank canvas for us to paint however we want to paint, and that is an exciting place to be.”

When did you stop solving the problems and start leading the people?

Reflecting on his years at Pinterest, Derrick Diaz describes the moment the work changed and the mentor who made it possible.

“I started in 2014, and the shift probably happened around 2017 or 2018. Before that, my team would manage something with my oversight, but I would still jump in to help and then jump back out. By 2017, I was working on the department’s long-term vision and letting the team do the work.

If you have come up as an individual contributor, you might think, and you might be right, that you could do each of those jobs better. But could you do all of them better at exactly the same time? It is better to support and uplevel people than to take your time away and focus it on one specific problem. You have to be comfortable with things not being at the same standard you would have set. I now get more enjoyment out of seeing someone else succeed where they were struggling than I ever did from doing the work myself.

I would not have been able to do this without Jesse Brooks, who mentored me at Pinterest. He would nudge my leg if he felt I was not thinking at a high enough level, and he reinforced the muscle of waiting in a room so that other people’s voices could be heard. I am a loud voice, and I have recognised that when I speak first, people simply go with my idea. So I have to wait in the silence and the discomfort until the person with a good idea feels compelled to speak. Candidly, that is my biggest personal challenge.”

What do organisations still misunderstand about the value of IT?

Derrick Diaz argues that infrastructure decisions are won or lost in the language of return on investment, not architecture.

“I was a technologist, and one of the things Jesse helped me learn was to be a financial storyteller. It is easy to say the business will need something in two years, so we should build it now. That is not inexpensive. It takes people on your team, and it takes away from today to build for the future.

No CFO and no CEO is going to say, “Sure, I will spend a million dollars on that; it sounds like a great idea.” You have to know every facet of the business so you can turn the conversation into an ROI conversation. This is where we unlock people. This is how much we lost by not moving fast enough. This is the tech debt. These are the five companies already ahead of us, and this is where they are in the market because of it.

Recently at the Guardian, we needed additional headcount, and we had been told the funding was already decided and not available. Because I had documented our OKRs and the people hours behind them, I could show them fifteen initiatives, explain that we could deliver eight, and that with the right hire we could deliver twelve. Within ten minutes they saw the trade-offs, realised they did not want them, and greenlit something they had already said no to.

I always like to give three options. In a perfect world, you give us nine headcount and here is everything we can do. Honestly, that will never happen, but that is where you start. The middle ground is what the department really needs. And if we cannot have any, there is no ill feeling; these are the things we can do. They are the heads of the business, and they are allowed to make that decision. My job is to give them the information so the decision is transparent.”

Has AI changed how you scope a project?

While pushing his team to use AI daily, Derrick Diaz is sceptical that anyone can yet measure honestly what it saves.

“Nobody knows. Agentic AI still functions best with an incredible amount of human oversight and knowledge. It cannot run on its own; it needs someone to steer it in the right direction. The best example is Jarvis and Tony Stark. Tony Stark is the genius who came up with the idea of the suit. AI can take work that would have taken a week of calculations and compress it into hours, but the initial idea, the verification and the oversight have to come from a human.

So how do you calculate that? At step C, the AI pushed us forward 50 per cent, and at step F it only pushed us forward 10 per cent. Sometimes it goes off in a direction that has nothing to do with the project, and you have to go back to scratch, which makes the work take longer. I still scope things exactly as I would have before, while pushing the team to use AI as much as possible.

There is no one ring, no one AI to rule them all. What is happening, similar to software, is that companies are becoming very good at their own verticals. The general platforms have swim lanes they are very good at, but outside those lanes they make a lot of mistakes. Once companies codify exactly how they help with the job you are doing, three or five years from now, it will be much clearer how much time is actually being saved.”

What do you focus on first when you inherit or build a team?

Derrick Diaz describes how he diagnoses whether the constraint is people, process or technology, and why he refuses to lead with a two-year vision.

“There is no single right way to do it. Some people are high performers who need you to unblock them so they can do their best work. Some need coaching up. Some need managing out, and a low performer makes other people feel they do not need to work as hard.

You talk to every single person on your team, then to the key stakeholders, and then to the people who are not senior but have loud voices. Those people are a gift; they are annoyed because they care that things are not functioning better. From there you work out whether the problem is people, process or technology, and you decide which one to lean into first.

Then you need quick wins. People get stuck because they announce a vision of what the department will be in two years and ask everyone to hold on. What if you are wrong? What if there are headwinds, or the budget changes? Execute medium-sized things every two months and quick wins every week and a half, so you keep positive momentum. You move at the speed of trust. If they do not trust you, you are not going to get anything done.”

What one question should every technology leader ask themselves?

Derrick Diaz closes with the question he repeats to his managers, and to himself, on a near-constant loop.

“What problem are we trying to solve? I think we get too lost in the sauce sometimes. Someone from the sales team asks whether we can integrate a product, and IT is reactionary: can we do it, is it compliant? We do not ask whether it is the right solution, or whether we will spend six months building something that solves today and is not helpful tomorrow.

We all come into a situation carrying scar tissue from bad decisions, difficult vendors, software that did not work or reporting structures we did not want. Asking what problem we are trying to solve pushes you past the initial no that comes from having been burned before.

It also protects the work. If you only know that you are building a piece of software and you hit a headwind, you are out. If you know the problem you are solving, you can manoeuvre around the obstacle and still solve it.”

Join the Conversation: The Ortus Club’s Executive Network

As Derrick Diaz and his experience has shown, the hardest problems in IT leadership are rarely technical. Securing investment, judging what AI can realistically deliver, and deciding whether the constraint in front of you is people, process or technology are all judgements that improve when they are tested against peers facing the same decisions.

His point about moving at the speed of trust applies well beyond the boundaries of a single department. Leaders building for markets two years ahead of the current business need somewhere to pressure-test those bets before committing budget to them.

At The Ortus Club, we host curated executive roundtables that bring together senior leaders facing exactly these decisions. Step away from the generic conversation about digital transformation and into the practical exchange of what has actually worked, and what has not.

FAQs Section

Q: What does it mean to move at the speed of trust?

A: It is the principle that the pace of any technology programme is set by the confidence stakeholders have in the team delivering it. Where trust is absent, integrations, approvals and cross-department work slow down regardless of technical readiness.

Q: What is a financial storyteller in an IT context?

A: A leader who presents infrastructure decisions in business terms: the revenue unlocked, the cost of delay, the accumulated tech debt and the competitive position, with the underlying research available but not required reading.

Q: How should IT leaders scope projects that involve AI?

A: For repeatable work where the time saved has already been observed, that saving can be built into the estimate. For novel work, Derrick recommends scoping as though AI were not involved, since its contribution varies too widely from step to step to forecast reliably.

Q: Why do quick wins matter when transforming an IT department?

A: They build the credibility needed to sustain a longer programme. Delivering visible improvements every week or two, alongside medium-sized wins every couple of months, earns the goodwill required when a multi-year initiative asks people to wait.

Q: What skills will the next generation of IT leaders need?

A: Intellectual creation and problem framing, cross-departmental collaboration, and the ability to articulate precisely what should be built. As AI lowers the barrier to execution, the differentiating skills become knowing what is possible, what is worth building, and how to review what has been made.