Chief of Staff in London

Location: Hybrid – London (head office) and home

Contract: Permanent, full-time

About Fifty Five Hospitality

Fifty Five Hospitality is creating a new brand of ultra-luxury hotels and resorts rooted in nature and wellness within easy reach of global gateway cities.

Our first hotel, Farthingstone, is a new-build ultra-luxury countryside hotel in Northamptonshire, less than two hours north of London, in an outstanding natural environment with an exceptional wellness offering. Future hotels will follow in prime international locations.

We are a small, private equity-backed team of experienced hotel executives, a two-Michelin-starred chef, and specialists from corporate, interior design and global creative backgrounds. As owner, developer, brand and operator, we are building a hospitality company from the ground up, so every hire is fundamental in shaping how we build and how we operate.

This is a rare opportunity to work side by side with the CEO at the centre of a business being built from a blank page, with exposure to development, brand, operations, investors and growth at the point where the foundations are laid.

Role Purpose

The Chief of Staff is a newly created role, reporting directly to the CEO and working closely with the wider executive team.

We are a high-horsepower business in build mode, moving at pace across development, brand and operations at the same time. The Chief of Staff brings structure, rigour and analytical capacity to the centre of the company. The mandate covers strategy and analysis, financial modelling, programme coordination across departments, the review of new opportunities, board and investor reporting, and the operating rhythm that keeps a growing team aligned.

This is a deliberately hands-on role with no team beneath it, and AI tools are central to how the work gets done. The successful candidate owns workstreams that are central to how the CEO leads the business, working directly with the CEO and alongside every head of department. Their work underpins the CEO’s ability to set strategy, make well-informed decisions and drive delivery across the company.

The person in this role will build the models, processes and reporting that a multi-asset platform needs before they are required, and there is real scope for the role to grow as the portfolio does.

Key Responsibilities

• Work closely with the CEO on strategy across every part of the business, from development and brand to operations, commercial and finance.
• Lead research, benchmarking and analysis to inform key decisions, covering hotel performance, capital expenditure, compensation, suppliers and the competitive set.
• Turn analysis into clear recommendations, and produce high-quality decks and presentations for the CEO, executive team, board and investors.
• Lead strategic projects from problem definition through to recommendation and implementation.
• Build and maintain the company’s financial and operating models, including scenario and sensitivity analysis.
• Prepare first-pass underwriting of capital expenditure and new opportunities.
• Keep models documented, auditable and ready to scale across a multi-asset platform.
• Track the pre-opening and construction programme across departments, mapping interdependencies and critical-path milestones.
• Identify cost, programme and quality risks early and bring them to the CEO with a clear view of options and consequences.
• Give the management team a single, consistent and structured view of progress across every workstream.
• Track departmental priorities and follow actions through to completion.

Opportunity Review

• Research, screen and analyse new opportunities, including sites, acquisitions and partnerships, before presenting them to the CEO.
• Establish a consistent review process so that every opportunity is assessed on the same basis and against the platform strategy.
• Support strategy, acquisitions and capital markets workstreams with research, pipeline analysis and investment materials.

Investor & Board Reporting

• Prepare drafts of board reports, investor memos, consent requests and responses to data requests for CEO review.
• Keep papers timely, accurate and consistent in quality as reporting demands grow with the platform.
• Maintain the trackers, data and records that underpin investor and board reporting.
• Own the preparation of weekly Management and Quarterly Meetings: agendas, pre-work, papers, minutes and action tracking.
• Run the company’s planning rhythm, including quarterly reviews of departmental priorities, reporting lines and resourcing.
• Document processes and institutional knowledge so that they are held by more than one person.

Onboarding & Culture

• Help new heads of department become effective quickly through structured induction, context and introductions across the business.
• Act as a clear point of contact for cross-team queries, and embed our ways of working and culture as the team grows.

Special Projects

• Lead ad hoc projects and requests from across the business as directed by the CEO, including tenders, vendor evaluations and policy work.

Candidate Profile

• Background in finance, strategy or management consulting, investment management, or project management in an operational business.
• Outstanding analytical and financial modelling ability: comfortable building an operating or investment model from a blank page and defending its assumptions.
• Hands-on, everyday use of AI tools in research, analysis, modelling and drafting, with sound judgement on where they add value and where they need checking.
• An excellent writer and presenter, able to turn complex analysis into clear, concise papers and decks for an executive, board or investor audience.
• Highly organised, with a track record of driving complex, multi-stakeholder programmes to deadline.
• Earns the trust of senior specialist colleagues through credibility and judgement, and handles confidential matters with discretion.
• Curious, rigorous and comfortable with ambiguity and pace in a small, PE-backed business; treats process and the right questions as seriously as the result.
• Hospitality experience is not required: sector expertise sits with our heads of department and General Manager, and the value of this role lies in structure, rigour and analytical capacity. Willingness to spend regular time on site at Farthingstone through construction and pre-opening is required.

What We Offer

• Competitive salary with discretionary annual bonus
• Enhanced pension scheme
• Salary sacrifice schemes (EV, cycle-to-work) available after probation
• Private medical and dental insurance
• 33 days’ annual leave (including bank holidays)

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