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Octopus Legacy

Octopus Legacy

Online estate planning and bereavement services

Account Executive

Full-Time
No salary listed
Mid
London, UK
Hybrid

Hybrid role: 3 days on-site in London Bridge per week, up to 2 days remote.

About the job

Requirements
  • 2 - 4 + years of experience in a sales role
  • Comfortable on the phone and in the demo, enjoy outbound work, confident running a structured demo, and able to adapt your style to whoever's in the room
  • Direct with prospects, with the team, with yourself; you set your own pace and build your own structure
  • You don't need managing; you can set your own pace and get on with it
  • You understand what it means to operate in FCA-regulated environments, Consumer Duty, and you take that seriously
  • Naturally curious; you dig into how a partner's business actually runs before the demo, understand their clients, their pain points and where we fit
  • You actually care about this; you can explain why bereavement support and estate planning matter - and make IFAs care too
  • You will own the deal from start to finish; you'll need the outbound hunger to go and find opportunities, and the relationship tact and commercial polish to close
  • Map your channel and build a targeted pipeline; identify right partners and convert them into long-term relationships that scale
  • Leverage existing relationships across the Octopus Group to open doors faster
  • Run deals end-to-end from first conversation to signed contract; navigate organisations with multiple stakeholders, run demos, align commercial terms and get ink on paper
  • Build partner-specific business cases that show how the platform adds value to their customers
  • Grow senior relationships within your channel; the kind of conversations where partnerships are shaped, not just sold
Responsibilities
  • Leverage existing relationships across the Octopus Group to open doors faster
  • Map your channel and build a targeted pipeline. Whether that's employer networks, IFA platforms, charities or financial institutions, you'll identify the right partners and convert them into long-term relationships that scale
  • Get us known. Whether that's speaking at industry events, doing outbound reach, hosting roundtables or simply being visible in your market. People know Octopus. This is a hunting role and about showcasing the breadth of what we can now offer
  • Run deals end-to-end. From the first conversation to a signed contract, you'll navigate organisations with multiple stakeholders, run demos, align commercial terms and get ink on paper
  • Build partner-specific business cases that show how our platform adds real value to their customers
  • Grow senior relationships within your channel. The kind of conversations where partnerships are shaped, not just sold
Desired Qualifications
  • Experience selling into financial services, IFAs, brokers or intermediaries is a strong plus, but not essential

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

Parental Leave

Wellness Program

Mental Health Support

Gym Membership

Cycle to Work Scheme

Home Office Stipend

Phone/Internet Stipend

Conference Attendance Budget

Professional Development Budget

Stock Options

Company Equity

Adoption Assistance

Childcare Support

Meal Benefits

Growth & Insights and Company News

Headcount

6 month growth

27%

1 year growth

27%

2 year growth

27%
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.