We're looking for a Chief of Staff to act as the CEO's strategic right hand and force-multiplier across a growing group of companies spanning healthcare, media, and software. You will keep the CEO organised, informed, and focused; own the operating rhythm, priorities, and reporting; oversee day-to-day finance and operations; and take work off the CEO's plate across both business and personal life.
This is not a traditional executive assistant role. You will own recruitment end to end, manage monthly financials, lead cross-functional projects, and represent the CEO with partners and suppliers as a trusted proxy. Full training on all company systems and processes will be provided — no prior healthcare experience is required. If you are highly organised, genuinely AI-native, proactive by default, and take pride in making a high-performing CEO more effective, this role is a strong fit.
Why You'll Want to Join
- You will be paid in USD (bi-monthly: every 15th and 30th)
- Paid Time Off in accordance with company policy
- Observance of Holidays per company guidelines
- 100% remote setup so you can work wherever you're most productive
- This role requires availability during UK business hours
- Act as a true strategic partner to a founder running multiple companies across healthcare, media, and software
- High-ownership, high-trust role with direct impact on how the business operates day to day
What You'll Work On
Executive Operations and Calendar Management
- Own the CEO's calendar end to end, protecting deep-work time, family commitments, and fixed priorities before adding anything new
- Create clear, complete calendar invites with full context, colour-coded by type, and conflict-free at all times
- Manage the CEO's inbox daily, surfacing only what requires his attention, drafting replies, and filing the rest
- Prepare the CEO for every decision with options, context, and a clear recommendation
- Run the operating rhythm including recurring team meetings, weekly reviews, and quarterly planning
Finance and Reporting
- Prepare the monthly profit and loss, run payroll, manage invoices, expenses, and budgets
- Coordinate with the accountant on tax and ensure records are organised and current
- Maintain simple dashboards and track key numbers across the group
- Deliver board and leadership reports accurately and on time
Projects and Operations
- Lead cross-functional and special projects end to end with full ownership of timelines, quality, and delivery
- Build, document, and continuously improve SOPs and systems across the business
- Track KPIs, OKRs, and priorities across all companies and keep the team aligned and accountable
- Manage vendor relationships, tool subscriptions, renewals, and negotiations
- Coordinate contractors and external partners on active workstreams
Recruitment and People Operations
- Own recruitment end to end including writing job specs, sourcing and screening candidates, coordinating interviews, and managing offers
- Build and maintain pipelines for both contractors and permanent hires
- Run onboarding for new starters and maintain team records and light HR administration
Communications and Stakeholder Management
- Act as communication liaison for clients, partners, and suppliers
- Manage follow-ups with leads and clients and support email campaigns
- Represent the CEO as a trusted proxy with high-level partners and stakeholders
- Prepare meeting agendas, notes, action lists, status reports, and slide decks
Personal and Family Support
- Manage the CEO's personal and family calendar including appointments, birthdays, and anniversaries
- Plan family events, celebrations, travel, and holidays
- Handle gifting, shopping, and personal admin including household management, bills, health appointments, and document renewals
- Manage personal finances including budgeting, receipts, and liaison with personal advisers
AI-First Workflow
- Use AI tools daily including Claude and ChatGPT as a core part of how you work, not as an afterthought
- Use AI to research, draft, summarise, and produce fast, high-quality first versions of documents, emails, and reports
- Continuously identify opportunities to automate and optimise processes using AI
- Build and maintain AI-assisted workflows and documents across the business
What You Bring
- Proven experience as a Chief of Staff, Executive Assistant, or Operations Lead supporting a founder or CEO, remote experience welcome
- Strong organisational and project management skills with the ability to manage multiple priorities across parallel workstreams simultaneously
- Solid finance and bookkeeping competency including profit and loss preparation, payroll, expense tracking, and budget management
- Genuinely AI-native with confidence using Claude, ChatGPT, and similar tools daily for research, drafting, and workflow optimisation
- Excellent written English with a clear, professional, and warm communication style
- Highly proactive, reliable, and discreet with the ability to handle sensitive business and personal information with full confidentiality
- Comfortable with spreadsheets, dashboards, and reporting tools
- Full-time availability during UK business hours
Nice to Have
- Experience supporting a founder or CEO across multiple business entities simultaneously
- Background in healthcare, pharmacy, media, or software company environments
- Experience owning recruitment end to end including sourcing, screening, and offer management
- Familiarity with tools such as Notion, Zapier, Calendly, or similar operations and automation platforms
- Prior experience managing both professional and personal delegations for a principal
How to Apply
Please include:
- Your updated resume
- A short Loom video (1 to 2 minutes) introducing yourself, describing your experience supporting a founder or CEO, and walking through a specific example of a system or process you built that meaningfully reduced your principal's workload
Only candidates who submit a Loom video will be moved to the next step of the hiring process.
If you are organised, AI-native, and want to be the operational backbone for a founder running multiple growing companies, this role gives you the trust, the variety, and the direct impact to do your best work.
Application Process Overview
Our comprehensive selection process ensures we find the right fit for both you and our clients:
- Initial Application - Submit your application and complete our prequalifying questions
- Video Introduction - Record an video introduction to showcase your communication skills and work experience
- Role-Specific Assessment - Complete a homework assignment tailored to the position (if applicable)
- Recruitment Interview - Initial screening with our talent team
- Executive Interview - Meet with senior leadership to discuss role alignment
- Client Interview - Final interview with the client team you'd be supporting
- Background & Reference Check - Professional reference verification
- Job Offer - Successful candidates receive a formal offer to join the team
Each stage is designed to evaluate your fit for the role while giving you insights into our company culture and expectations. We'll keep you informed throughout the process and provide feedback at each step.
