Head of Technology & AI

Hiire is supporting Draycott Hiring for a Head of Technology & AI!!
Are you ready to turn every match into a story?
Who We Are
Draycott is a diversified alternative asset manager, with the ambition to place alternatives within reach of Iberian savers. We invest across four complementary strategies - Private Equity & Growth, Real Estate, Venture Capital and Fund of Funds - under a single underwriting discipline and a consistent value-creation playbook.
Built on nearly two decades of investing and brought together as an institutional platform in 2022, Draycott today manages more than €3 billion in alternative assets. In june 2026 we acquired 100% of Square AM - the largest open-ended real estate fund manager in the Iberian Peninsula - which for the first time gives us presence in the banking channels where Portuguese people actually save.
We intend to be the most technologic and AI-driven alternative asset manager in Iberia. Not as a slogan, and not as an efficiency programme running quietly in the background, but as a deliberate choice about how this firm works - AI inside the investment process itself, our own information treated as a proprietary asset, and a deliberately lean organisation supported by exceptional tooling rather than by headcount.
The Role
It is in this context that we are looking for our first Head of Technology & AI.
This is one of the most consequential hires we will make, and it is not an IT management role. You will own the technology agenda and the budget behind it, including real money for experimentation. You will sit in front of our board and Investment Committee, work directly with the CEO and the leadership team, and lead a theme that is central to where this firm is going - with a clear path to a C-level mandate as the platform scales.
Expect a fast pace, real ambition and a team of exceptional people. At this level we do not write policies about presence: you will be with the team because that is where the building happens and you will own your own calendar.
What You'll Do
AI at the core of how we invest and operate. Bringing AI into the investment process itself and into how the firm runs day to day, and treating the information we generate as an asset to be structured, accumulated and put to work.
A real innovation practice. Short experiments with honest kill criteria, and the discipline to industrialise what works. Not a lab that sits to the side of the business.
The technology behind our products and our growth. Owning the platforms and tools through which our products reach investors, and the build-versus-partner decisions, partners and delivery behind them.
The firm's technology foundations. Our IT, security, resilience and data governance and the team you will build to run them.
Value creation in our portfolio companies. A repeatable AI and digital playbook applied inside the businesses we own, delivering measurable operational and financial impact. This is a value-creation lever with a direct line to multiples, not an advisory exercise.
What We're Looking For
We are hiring for profile and trajectory, not for domain expertise in asset management technology. That is learnable. What we cannot teach is the following.
A steep trajectory. Your scope has grown faster than your years. The shape of this role will change several times over the next three years, and we are hiring for where it is going.
A track record of building and launching something real, and owning the outcome (a product, an operation, a business) taken from zero to live, with real users and real deadlines. What you owned, not what you recommended.
You are at the frontier of AI, not commenting on it. You use these tools daily, you have replaced real processes and can describe the before, the after and what failed, and you can pull an organisation with you, by teaching and persuading rather than by issuing a policy.
Innovation instinct with the discipline to match. You experiment cheaply, kill what is not working without drama, and industrialise what is.
Genuine engineering and architecture literacy. You can judge a design, choose a partner, and earn the respect of the people you hire whether or not you still write code.
A lean instinct. You would rather deliver with a small, excellent team and the right partners than build an empire.
Credibility across very different rooms such as our leadership team, an owner-manager of a portfolio company, a large institutional counterpart, and taken seriously in all of them.
High ownership, structured thinking, and comfort with ambiguity and pace. Typically 8–15 years of experience. Fluent Portuguese and professional-level English.
Who You Are
The strongest candidates for this role tend to share a few things in common:
You're the kind of person where technical skill gets you in the room; patience and change-management instinct are what get the job done there.
You measure yourself the way the business will measure you: by whether the people you support actually feel helped, not by how elegant your architecture is. You think like an internal service provider as much as a technologist.
You don't need a team to feel useful. Guiding someone earlier in their career (in this case, a junior AI Coordinator) is part of how you work, not a distraction from it.
You're equally comfortable owning unglamorous infrastructure and the ambitious, visible AI agenda.
You've probably operated in both a large, structured organisation and a smaller, scrappier one, and you know how to borrow the discipline of one without losing the speed of the other.
What We Offer
A dual mandate from day one, not a slow ramp-up. You'll run the AI/technology agenda with real, visible projects already lined up and integrating the tech and processes of a newly-acquired company still running manually.
A team you shape yourself. You start small and autonomous, with headroom to grow.
Trust over hierarchy for success. You're not judged against an abstract scorecard. Success is defined by the teams you actually support telling us the impact was real.
A real seat at the table, direct access to the CEO and leadership team, and a defined path to a C-level mandate as the platform scales.
This is an on-site position in our Amoreiras office.

Work arrangement
No