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Octopus Legacy

Online estate planning and bereavement services

Executive Assistant

Full-Time
No salary listed
Junior
London, UK
HybridRemote up to 4 weeks per year; London-based role with occasional global remote work."
Administrative & Executive AssistanceExecutive Support

About the job

Requirements
  • 2+ years' experience in a PA or EA role, ideally supporting busy teams or senior leaders
  • Highly organized: you juggle multiple priorities effortlessly while keeping every detail in check. From financial accuracy to managing diaries, nothing slips through the cracks.
  • Confidentiality: you're a vault. Handling sensitive documents, payroll, and financial transactions with absolute discretion is second nature to you.
  • Proactive Problem-Solver: you see challenges as opportunities and are always thinking two steps ahead, finding smarter ways to get things done.
  • Clear communicator: you keep things simple and straightforward.
  • Adaptable & Flexible: you're not fazed by change and thrive when things shift gears quickly.
  • Team player: you love collaboration. You bring a positive attitude, create a sense of community, and help make the workplace an inspiring place to be.
Responsibilities
  • Manage the founder's calendar, keeping appointments, meetings, and calls running smoothly and efficiently.
  • Keep on top of emails, draft responses, and prioritise requests to make sure nothing slips through the cracks.
  • Support with payroll, invoices, and expenses, ensuring accuracy and deadlines are met.
  • Organise team events, all-hands meetings, and team-building activities that bring everyone together and keep things fun.
  • Make sure the office runs seamlessly - from supplies to mail to those last-minute ad hoc requests.
  • Lead the charge on creating a fun, engaging, and collaborative workplace culture.
  • Jump into ad hoc tasks and special projects, ready to roll with the needs of a fast-paced startup.

About the company

Octopus Legacy offers estate planning and bereavement support in the UK, combining online will writing, Lasting Power of Attorney forms, life insurance, probate services, and bereavement resources on a single platform. It works through direct-to-consumer channels and partnerships with charities, employers, and funeral directors; its will-writing product is subscription-based with unlimited updates, and users can store digital memories in a digital vault alongside legal documents. The company differentiates itself by providing a holistic, customer-focused platform that covers legal, financial, and emotional planning, backed by strategic acquisitions and Octopus Group capital to scale. Its goal is to simplify and consolidate the fragmented death-planning market into an accessible, end-to-end solution for end-of-life planning and legacy management.

Company Size

51-200

Company Stage

N/A

Total Funding

N/A

Headquarters

London, United Kingdom

Founded

2018

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Simplify's Take

What believers are saying

  • Octopus Legacy treble-sized to 57 staff by January 2025, signaling rapid operating momentum.
  • The NewLaw team acquisition boosted probate capacity and expanded Octopus Legal Services by roughly one-third.
  • Octopus Group's 2022 investment funded scaling, acquisitions, and a trusted Octopus consumer-brand halo.

What critics are saying

  • Legal Futures said Octopus will grow probate 1,000% without adding frontline legal hires, straining quality.
  • Shoosmiths transferred no staff, forcing Octopus to absorb files while retraining and onboarding alone.
  • Death-planning is fragmented and trust-sensitive; one service failure would damage referrals and employer partnerships fast.

What makes Octopus Legacy unique

  • Octopus Legal Services launched in January 2025, bringing probate inside an SRA-regulated ABS.
  • WSL Will Writing added 300,000 clients, making Octopus Legacy Britain's second-largest estate planner.
  • Shoosmiths' 2026 will-bank acquisition deepens regulated scale and strengthens its consumer brand.

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Benefits

  • Health Insurance
  • Pension scheme
  • Family Planning Benefits
  • Fertility Treatment Support
  • 401(k) Retirement Plan
  • 401(k) Company Match
  • Flexible Work Hours
  • Hybrid Work Options
  • Remote Work Options
  • Unlimited Paid Time Off
  • Paid Vacation
  • Paid Holidays

Growth & Insights and Company News

Headcount

6 month growth

24%

1 year growth

24%

2 year growth

24%
Today's Media
Apr 24th, 2026
Octopus Legacy acquires Shoosmiths will bank in push to become UK's largest estate planner

Octopus Legacy has acquired the will bank of Top 100 law firm Shoosmiths, strengthening its position in regulated estate planning. The deal follows Octopus Legacy's acquisition of WSL Will Writing in the past 18 months, which brought over 300,000 clients and positioned it as the UK's second-largest estate planning firm. Sam Grice, founder and CEO of Octopus Legacy, called the acquisition "an important milestone" and testament to the company's growth within the regulated space. The firm aims to become the largest private client firm in the country whilst modernising estate planning services. For Shoosmiths, the transfer aligns with its strategy of focusing on core practice areas, following previous sales of its private client team to Rothley's and personal injury business to Fletchers.