Chief of Staff (AI)

Location: Remote across the United Kingdom, Belgium, Spain, Portugal, or South Africa, working UK hours. A week in Jersey each month is required during the first quarter, followed by quarterly visits and one annual offsite.

Salary: £40,000–£95,000 base per year, depending on experience and location, plus equity and an outcomes bonus.

Company

A founder-led group of B2B software companies focused on private wealth, governance, compliance automation, board minutes, and media strategy.

What you will do

• Run the operating rhythm across the group, including daily check-ins, weekly business reviews, Friday updates, and the decision log.
• Take ambiguous workstreams such as funding mechanics, alliance agreements, pricing improvements, and specialist pools from discussion through recommendation and execution.
• Prepare concise one-page decision briefs and curate the information reaching the founder.
• Close operational loops across advisers, counsel, company secretaries, candidates, investors, and co-founders.
• Run hiring processes with the recruiter, including scorecards, interviews, references, trials, and onboarding.
• Manage operating administration such as payroll, banking within limits, tools, and filing calendars until ownership is transferred.

Requirements

• Exceptional writing skills, including turning complex conversations into clear one-page recommendations.
• Experience closing loops across people who do not report directly to you.
• Comfort working with senior stakeholders and acting with delegated founder authority.
• Numeracy, discretion, and the ability to handle cap tables, salaries, payroll, and banking within defined limits.
• Daily practical use of AI for research, drafting, analysis, and automation is required.
• Either six to ten years of chief-of-staff or operating experience, or strong founder's associate experience with the ability to grow into the role.

Nice to have

• Previous experience in a small company with incomplete systems.
• Experience working with B2B software, private wealth, governance, or compliance businesses.

Culture & Benefits

• Remote work on UK hours with periodic in-person time in Jersey.
• Equity participation and an outcomes-based bonus.
• Home office, learning, wellbeing, and AI tool budgets.
• A sustainable working pace, with a deliberate slowdown after the annual reporting crunch.
• A written progression path toward head of operations or a new line of business.

Hiring process

• Short paid writing exercise and paid working session using anonymised real tasks.
• Conversations with the founder and a co-founder, followed by references.
• Paid trial and a sixty-day review against agreed outcomes.