Executive Assistant to Chief Executive Officer

Octopus Legacy; Greater London; Hybrid; GBP 38,000 - 60,000; Full time

Benefits offered by this job

Flexible working: 3 days in the office

2 days remote

Work from anywhere up to 4 weeks/year

Health & Life Insurance

Enhanced parental leave

Free Will & LPAs

Cycle to Work Scheme

Dog-friendly office

Snacks and wellness activities

Job summary

Octopus Legacy Limited is seeking a sharp, commercially minded Executive Assistant to work closely with our Founder. This role goes beyond diary management; you will run the inbox, ghostwrite on behalf of Sam, and judge which tasks deserve his time to drive the business forward.

You’ll align with company priorities, manage calendar focus, and support budgets, payroll, and key partnerships. This is a great step up for someone with 2+ years in a PA/EA role who wants real responsibility in a

Qualifications

• 2+ years in a PA or EA role, ideally supporting a founder, CEO or senior leader in a fast-moving environment.
• Strong writing: able to mirror voice and draft clear, confident emails and documents.
• Discreet handling of sensitive payroll, financial and personal information.
• Proactive and two steps ahead: anticipate needs and close loops without prompting.
• Ruthless prioritisation: protect time and say no when required; calm under pressure.

Responsibilities

• Own Sam's inbox end to end: triage, action, delegate, archive.
• Draft and send emails and messages in Sam's voice for partner follow-ups and investor updates.
• Write first drafts of internal memos, all-hands notes, briefing documents and talking points.
• Manage Sam's calendar strategically, protecting focus time and prioritising high-value meetings.
• Prepare for each meeting: who, why it matters commercially, desired outcomes and follow-ups.
• Support payroll, invoices and expenses with accuracy and deadlines.
• Organise all-hands, team events and offsites within budget; keep the office running smoothly.

Skills

Inbox management

Calendar management

Written communication

Prioritisation

Discretion

Proactivity

Adaptability

2+ years PA/EA experience

Tools

Gmail/Outlook

Calendar tooling

Slack

Job description

We're Octopus Legacy: one of the fastest-growing tech companies in the country, part of the UK's most exciting and best-trusted group (you may have heard of some of our sister companies…), and we have a mission.

We're on a path to scale, aiming to become a household name while transforming a long-established industry and helping our customers prepare for, and find support after, death.

But we can't do it alone, and that's why we're assembling a team of top performers to build with us.

Ready to be part of something big?

The Role

We're looking for a sharp, commercially minded Executive Assistant to work hand-in-hand with our Founder, Sam. This isn't a diary-and-travel role. You'll be Sam's right hand: running his inbox, writing on his behalf, deciding what deserves his time and what doesn't, and making sure the things that move the business forward actually get done.

You’ll understand what we're trying to achieve as a company (our targets, our partners, our priorities this quarter) and use that to make good calls without being asked. When a hundred things land at once, you’ll know which three matter.

This is a great step up for someone with 4+ years in a PA or EA role who wants real responsibility, real exposure to how a scaling business is run, and a seat close to the decisions.

Key Responsibilities

Inbox ownership and ghostwriting

• Own Sam's inbox end to end: triage, action, delegate, archive. Get it to a place where Sam only sees what genuinely needs him.
• Draft and send emails, messages and replies in Sam's voice, from partner follow-ups and investor updates to team announcements and LinkedIn posts.
• Write first drafts of internal memos, all-hands notes, briefing documents and talking points so Sam starts from 80% rather than a blank page.
• Know when to reply on his behalf, when to flag, and when to hold.

Prioritisation and protecting time

• Manage Sam's calendar strategically, not just logistically: protect focus time, push back on low-value meetings, and make sure his week reflects the company's priorities.
• Run a clear, live view of what's on Sam's plate, what's waiting on others, and what's slipping, and chase it.
• Prepare Sam for every meeting that matters: who he's meeting, why it matters commercially, what we want out of it, and the follow-ups afterwards.
• Make judgement calls under pressure and keep things moving when priorities shift mid-week.

Commercial support

• Understand our business model, key metrics and quarterly goals well enough to spot what's commercially important in a busy inbox or diary.
• Support on partner, investor and board activity: scheduling, preparing packs, tracking actions and keeping relationships warm.
• Track key commercial follow-ups (partnerships, deals, introductions) so nothing valuable goes cold.
• Manage budgets for events, suppliers and office spend, negotiate with suppliers, and look for ways to get better value.
• Support with payroll, invoices and expenses, ensuring accuracy and deadlines are met.

Team and culture

• Organise all-hands, team events and offsites that bring everyone together, delivered on budget.
• Keep the office running smoothly, from supplies to mail to last-minute requests.
• Help shape a fun, engaging and collaborative culture as we scale.
• Jump into ad hoc tasks and special projects as the business needs.

Who Are You?

• 2+ years in a PA or EA role, ideally supporting a founder, CEO or senior leader in a fast-moving environment.
• Commercially minded: you're curious about how the business makes money and what drives growth. You read the inbox and the diary through that lens, and you can tell the difference between busy and valuable.
• A strong writer: you can pick up someone's tone quickly and write clear, warm, confident emails and documents that sound like them, not like an assistant.
• A ruthless prioritiser: you're comfortable saying no (politely), you protect time like it's money, and you're calm when everything feels urgent.
• Proactive and two steps ahead: you anticipate what Sam needs before he asks and close loops without being chased.
• Discreet: you handle sensitive documents, payroll, financial and personal information with absolute confidentiality.
• Adaptable: you thrive when plans change at short notice and you're happy to roll up your sleeves.
• A team player: you build good relationships across the business and help make the workplace somewhere people want to be.

Our Mission

When people think about planning for death they think about wills, life insurance and funerals. We take these cold processes and turn them into something more human. Share more than money: leave voice notes, music, recipes. Shape a legacy that connects you while you're here. And after you're gone.

Founded by Sam after his mum died suddenly, we're a group of people who work in death because we've been affected by it. We know the difference a good plan makes, and what it's like when there isn't one.

Death can come between us, leave mess, legal fees, frustration. But it can also make us stronger. We see a world where people talk openly about death, and work out the real meaning of legacy, one that connects to them. We're here to make that world happen.

• Flexible working: 3 days in the office (London Bridge), 2 days remote
• Flexible holiday, plus an extra day off for your birthday
• Work from anywhere in the world for up to 4 weeks per year
• Vitality Health & Life Insurance
• Enhanced parental leave
• Free Will & LPAs, plus discounts on other Octopus services
• Cycle to Work Scheme and access to the EV Salary Sacrifice Scheme
• Octopus Giving: we match any charitable fundraising you do, up to £500
• Octopus Springboard: we help our employees become fully-fledged entrepreneurs
• Dog-friendly office
• Snacks and wellness activities

We know that to be truly innovative, we need a diverse team around us. That's why Octopus Legacy is committed to creating an inclusive environment and is proud to be an equal opportunity employer.