Role Summary: The right hand to a founder across his personal life and ventures — solving problems, running research projects, planning trips and turning ideas into reality, so he's free to focus on what only he can do. A hands-on role from day one, with genuine scope to grow as far as the right person can take it.
This is a remote-first role based in Spain — candidates must currently be a Spanish resident. Occasional in-person time with the founder should be expected as trips and projects require.
Who you'd be working with
Harry is a founder who's spent 10+ years building from scratch — not once, but repeatedly.
At 18 years old he founded TAILORED ATHLETE, a premium menswear brand, and has built other successful brands alongside it — together serving 1m+ customers across 100+ countries.
But the numbers aren't really the point. What actually defines Harry is his belief that anything is possible — that with enough time, knowledge and perseverance, you can make the wildest ideas become reality. He does nothing half-hearted, and measures himself on one thing: knowing he's done everything he possibly could at that moment in time.
This role is about getting close to someone who operates like that — becoming a true extension of him, taking the weight off his plate so he can build, create and make a genuine dent in the world. You free him to do what only he can.
The role
You'll be the founder's right hand across his personal life and ventures — solving problems, working out the smartest way to get things done, running research projects that come back with a recommendation rather than a raw dump, planning epic trips, owning the calendar and inbox, and turning ideas and plans into things that actually happen.
It's built to grow. This starts hands-on and execution-first, but for the right person it can evolve into something far bigger — owning entire projects end-to-end, running the founder's ventures operationally, and becoming a true right hand as trust and capability compound. The ceiling is set by how far you can take it, and those who grow into it will be rewarded accordingly.
So the question is: are you ready to own the detail, earn a founder's trust, and grow as far as your ability takes you? If you're already screaming a big YES, keep reading.
What's in it for you
We are your biggest fans in becoming the best version of ourselves and helping you lead a healthy life inside and outside of work. Here are the highlights of how we support you doing just this.
- Real ownership from day one — not task-ticking. You'll run your own workload with high trust and minimal micromanagement, and see the direct impact of your work in how much the founder can focus on what only he can do
- An unusually broad remit — few roles span this much. Personal life, travel, research projects and the operational detail behind multiple ventures, all in one seat
- A genuine path to grow — this role is built to expand as far as the right person can take it, from executing tasks to owning workstreams and projects independently, with real reward for those who grow into it
- Direct proximity to a founder — a rare, close-up view of how someone actually builds, decides and operates day to day, working side by side with him
- Level up on the best tools — real investment in training you on AI and modern systems, so you get sharper and more capable the longer you're here
- Remote-first and flexible — based in Spain, working on your own initiative, with occasional in-person time as trips and projects require
- Competitive compensation (pending benchmarking)
You'll work closely with the founder within a world that lives by these values: honest and open, learning and growing, vision, and 'we get things done.'
What you will be doing
Research & Problem-Solving
- Take an open-ended brief and run it end-to-end — investigate, weigh up the options, and come back with a clear recommendation and next steps, not a pile of raw information
- Run personal optimisation projects — audit how something's currently done and surface the highest-impact improvements
- Scope out business challenges and map how to actually implement solutions, from tools to process
- Source and secure whatever's needed — suppliers, services, venues, purchases — shopping around and landing on the best option, not just presenting a list
- Own agreed projects through to real implementation, not just the recommendation
Life
- Own the founder's calendar and inbox as gatekeeper — triage, protect his time, and surface only what genuinely needs him
- Design and book seamless end-to-end travel — flights, transfers, stays, and itineraries that actually work across time zones
- Curate tailored plans for every trip and land the hard-to-get bookings
- Provide fast, on-the-ground support while he's travelling — "I want to do X tonight" comes back as a shortlist with a recommendation, quickly
- Stay ahead of life admin before it becomes urgent — renewals, appointments, documents, deliveries handled quietly in the background
Business
- Provide the operational backbone behind whatever venture he's building or exploring
- Keep things moving — documents signed, approvals and payments chased, nothing stuck waiting on him
- Coordinate across teams and chase actions to done, without stepping on the people who own the work
- Represent him well to external partners, vendors, and suppliers
Systems & Growth
- Use AI tools (Claude and beyond) to work faster and raise your own output from day one
- Build and maintain the SOPs and trackers that keep recurring work running smoothly
- Use quieter periods to learn, build systems, and get ahead — never idle
Who you are
You might have a couple of years in a PA, EA, ops or coordination-heavy role — or you might not have the exact title, but you've got real proof of running complex, moving parts to a high standard, and you're hungry to go further.
- You're coachable — you take direct feedback on the chin, act on it fast, and never take it personally. Being told how something should be done is exactly how you want to work
- You're hungry to master things — you go deep on a new tool or system until you can run it properly end-to-end, not just dabble. You're already comfortable with AI tools like Claude and genuinely excited to go further
- You adapt fast — you pick up how someone likes things done and mould to it, and you learn new tools quickly (Slack, Asana, Google Workspace, or whatever's put in front of you)
- You have real judgment and taste — you make good calls with limited direction, and you know the difference between handling something yourself and when to check first
- You can be trusted completely — with sensitive personal and financial information, discretion isn't a performance for you, it's just how you operate
- You're self-directed — you generate your own momentum in the quiet periods and thrive in the peaks, without needing to be managed
- You're warm and easy to have around — socially fluent enough to hold your own at a dinner, on a trip, or in a room full of people you've just met
- You're motivated by ownership and trust — not a rigid job description — and excited by a role that can grow as far as your ability takes it
You're encouraged to apply even if your experience doesn't precisely match the job description. We are committed to creating a safe, diverse, inclusive and empowering culture at TAILORED ATHLETE, free from discrimination. It is our responsibility to ensure employee wellbeing and diversity is celebrated, embraced and at the forefront of our culture.
If you have any questions or would like a casual conversation about the role, please email [email protected].