Executive Assistant

Octopus Legacy Limited; Greater London; Hybrid; GBP 40,000 - 60,000; Full time

Benefits offered by this job

Flexible working (3 days in office)

Flexible holiday and birthday day off

Work from anywhere up to 4 weeks/year

Vitality Health & Life Insurance

Enhanced parental leave

Free Will & LPAs discounts

Cycle to Work Scheme

Octopus Giving match donations

Octopus Springboard

Dog-friendly office

Snacks and wellness

Job summary

Octopus Legacy Limited is seeking a sharp Executive Assistant to work closely with the Founder. This role goes beyond diary and travel management, acting as the right hand to prioritise work that moves the business forward.

You'll manage the inbox end-to-end, draft in Sam's voice, guard time, and support on partner, investor and board activity. Flexible, hybrid London work with exposure to a scaling tech business.

Qualifications

• 2+ years in a PA or EA role, ideally supporting a founder or senior leader in a fast-moving environment.
• Commercially minded: understands how the business makes money and drives growth.
• Strong writing style that matches the leader's voice.
• Ruthless prioritisation: protects time and says no when needed.
• Proactive and two steps ahead, able to close loops without chasing.
• Discretion with confidential documents, payroll and personal data.
• Adaptable to changing plans and able to roll up sleeves.
• Team player who builds relationships across the business.

Responsibilities

• Inbox ownership and ghostwriting: triage, action, delegate, and draft in Sam's voice.
• Draft emails, investor updates, partner follow-ups, and LinkedIn posts.
• Prepare memos and briefing documents to start from 80%.
• Know when to reply, flag, or hold on behalf of Sam.
• Calendar management: protect focus time and prioritise meetings.
• Provide a live view of Sam's plate and chase progress.
• Prepare for key meetings with context on commercial relevance and outcomes.
• Make quick, reasoned calls when priorities shift.
• Understand our business model, metrics, and quarterly goals.
• Support partner, investor and board activity: scheduling, packs, tracking actions.
• Track follow-ups and manage budgets for events and office spend.
• Assist with payroll, invoices and expenses accurately and on time.
• Organise all-hands, team events and offsites within budget.
• Keep the office running smoothly and help shape a collaborative culture.
• Jump into ad hoc tasks and special projects as needed.

Skills

Executive support

Diary management

Written communication

Prioritisation

Calm under pressure

Discretion

Team collaboration

Stakeholder management

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.

We’re tackling some of the biggest taboos surrounding death. Together, we can help to make some of the toughest times in people’s lives easier.

Take this free 1-minute quiz. You’ll find out how prepared you are, and how to improve.