The Company

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

As a Graduate Compliance Associate, you'll play a key role in helping to prepare clear, legally sound estate planning documents, learning how to ensure accuracy, compliance, and quality at every stage. Working alongside our experienced legal and estate planning teams, you'll develop a deep understanding of estate planning while supporting clients through what can often be a complex and emotive process.

You'll join a forward-thinking team that's driving innovation in estate planning. We foster a dynamic, supportive environment where curiosity, adaptability, and ambition are valued. This is an excellent opportunity for a recent graduate to build the foundations of a long-term legal career, with full training, mentorship, and genuine scope to grow with the business.

Key Responsibilities

• Support the review of wills, LPAs, and estate planning documents to ensure they are legally binding and reflect the client's wishes
• Assist with registering documents with the Office of the Public Guardian and respond to client queries with guidance from senior colleagues
• Work closely with legal teams to learn how complex estate planning needs are managed
• Build your knowledge of will-writing regulations, inheritance laws, and industry best practices
• Maintain strict confidentiality and data security when handling client information
• Help carry out compliance checks on customer returns, contributing to a full audit trail
• Provide administrative support across will drafting and estate planning services

Who Are You?

• A recent graduate, ideally with a degree in Law or a related discipline (essential)
• A genuine interest in estate planning, private client work, or building a career in legal services
• Strong attention to detail and accuracy, with a commitment to producing high-quality work
• A collaborative approach and willingness to learn from legal professionals and estate planning colleagues
• Excellent communication skills, with the ability to explain information clearly and empathetically

Our Mission

Octopus Legacy is the place to plan for death and find support after loss. 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, leaving 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.

Benefits:

• Octopus share incentive scheme.
• Hybrid working (London Bridge).
• Flexible holiday + extra day off for your Birthday.
• Work from anywhere in the world for up to 4 weeks per year.
• Vitality Health & Life Insurance. 
• Pension scheme.
• Enhanced parental leave.
• Free Will & LPAs + discounts on other Octopus services.
• Cycle to Work Scheme and access to the Electric Vehicle (EV) Salary Sacrifice Scheme.
• Octopus Giving: we match any charitable fundraising that you do up to £500. 
• Octopus Springboard: where we help our employees become fully-fledged entrepreneurs.
• Dog friendly office.
• Breakfast every day, snacks and wellness activities.

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

The Company

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?

Start your career in Estate Planning – with the opportunity to qualify as a Private Client Solicitor

We’re now offering career changers to start their career in estate planning, with the opportunity to transition into private client legal work or develop into a permanent Estate Planning Consultant role (Field Sales), depending on your interests and skills.

Cohort starts mid-May - UK Based

📍 United Kingdom
🚗 You’ll need a valid UK driving licence and access to a car to travel to client appointments locally.

The Role

As a trainee Field Sales Consultant, you’ll support families with one of life’s most important conversations - how to prepare for the future. Through home visits and virtual appointments, you’ll help people understand the options available for wills, trusts, and powers of attorney, and guide them through next steps with care and clarity.

This is a hands-on role that’s perfect if you want to explore legal, client-facing work in a meaningful area, build practical experience, and develop deep knowledge of estate planning in real-life situations.

Responsibilities: 

• Conduct empathetic, detailed consultations with clients - either at home or online - to understand their wishes and walk them through their options
• Explain how wills, trusts, and lasting powers of attorney work in practical, jargon-free terms
• Keep accurate records and ensure the client’s decisions are clearly documented
• Collaborate with our legal team to stay up to date on legal standards and requirements
• Assist with online wills and other services across the business as needed
• Deliver exceptional aftercare - answering questions and helping clients make changes when life shifts

Who Are You?

This opportunity is ideal for:

• Career changers looking for a purpose-led, people-facing profession, preferably from a regulated background
• Individuals curious about building legal experience outside of the traditional path
  
• Candidates who want a structured training program learning about estate planning

We’re looking for people who are:

• Excellent communicators, with strong emotional intelligence
• Comfortable working independently, flexibly, and remotely
• Highly empathetic, with a genuine interest in helping others
• Organised and confident with sensitive conversations
• Comfortable driving within your local region for home appointments
• (Bonus but not required) Knowledge of wills, trusts, LPAs, or STEP qualification

Where Could This Role Take You?

Depending on your performance, interests, and qualifications, you could:

• Transition into a full-time Estate Planning Consultant (Field Sales)
  
• Be supported to train and qualify as a Private Client Solicitor
  
• Explore internal progression within our wider legal, sales, or customer service teams
  

We’ll support your development, provide training, and offer exposure to one of the most human sides of legal work.

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.

Benefits:

• Octopus share incentive scheme.
• Flexible holiday + extra day off for your Birthday.
• Vitality Health & Life Insurance. 
• Pension scheme.
• Enhanced parental leave.
• Free Will & LPAs + discounts on other Octopus services.
• Cycle to Work Scheme and access to the Electric Vehicle (EV) Salary Sacrifice Scheme.
• Octopus Giving: we match any charitable fundraising that you do up to £500. 
• Octopus Springboard: where we help our employees become fully-fledged entrepreneurs.

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

Role Summary

The General Manager will work closely with the CEO to lead Octopus Legacy towards its ambition of becoming the UK’s defining brand in estate planning and support after loss. Estate Planning is the core engine of the business - driving revenue, customer growth, brand trust, and long-term value creation.

This role carries full end-to-end accountability for the unit’s performance, growth and transformation. The GM will own strategy, commercial performance, operational delivery, people leadership, and customer outcomes.

Beyond running the business, this role will lead a critical evolution: transitioning Estate Planning from a predominantly service-led model to a scalable, technology-enabled platform that delivers exceptional customer outcomes and margin strength.

You will guide the business through a period of rapid growth and increasing complexity, stabilising and scaling operations, embedding systems and processes for efficiency, and taking full P&L ownership - all while working closely with the founder and executive team to shape the future direction of the business.

Key responsibilities

• Define and deliver a clear short and long-term strategy for the Estate Planning business that directly supports Octopus Legacy’s broader ambition and growth plans.
• Oversee all aspects of the business unit, including revenue, service delivery, and operations.
• Take full ownership of commercial and operational performance, translating strategy into clear KPIs, measurable outcomes, and disciplined execution across teams.
• Partner with Marketing and New Business to drive viral growth, strengthen the brand, and scale lead generation and conversion. 
• Partner with Product and Technology to prioritise and accelerate initiatives that improve systems, tooling, and workflows, driving operational efficiency and scalability. Build a best-in-class technology platform connecting our products and customers.
• Develop and manage financial resources, including budgeting, forecasting, and reporting to ensure sustainable growth and success.
• Take complex, ambiguous problems and opportunities from definition through to delivery, working ‘hands-on’ across teams to remove blockers, improve ways of working, and embed outcomes.
• Maintain rigorous compliance with all legal and regulatory requirements, embedding robust quality assurance and risk management processes.
• Build and maintain strong relationships with key internal and external stakeholders — including customers, partners and industry bodies — to strengthen our market position and reputation.
• Lead and strengthen our high-performance, customer-first culture during rapid scale (c.150 → 300 team size), reinforcing high standards of accountability, behaviour and results.
• Attract, recruit, develop and retain an exceptional team, building succession depth for critical roles.
• Anticipate market, regulatory and operational risks, and respond with structured, forward-looking action.
• Build the organisational scaffolding required for a scaling business unit — formal enough to ensure clarity and control, but lean enough to maintain momentum and entrepreneurial pace.
• Partner closely with the CEO, Board, and HoF team as a trusted senior operator, aligning Estate Planning priorities with company direction while helping to shape that direction.

What Success looks like

• Successful introduction of new products or service enhancements measured by time-to-market, ROI and customer satisfaction.
• A fully embedded, data-led operating cadence with clear accountability and performance visibility across all functions.
• High retention of top performers and a strengthened leadership bench across the business unit.

Profile & Approach

• Proven track record leading and scaling service-led businesses, bringing out strong performance in leaders while modelling accountability and high standards.
• Sets ambitious expectations for self and others; comfortable raising the bar and upgrading capability where needed.
• Strong commercial acumen and financial fluency, including budgeting, forecasting and advanced Excel skills.
• Comfortable leading change and driving clarity, pace and outcomes in ambiguous fast-paced environments. 
• Approaches problems structurally - capable of stepping into issues when required, but focused on building systems that prevent recurrence.
• High integrity and strong awareness of operating within regulated environments.
• Self-starting, with a strong sense of ownership and pace.
• Bias toward technology and automation as enablers of scale and efficiency.
• Strong product judgement with the ability to refine and expand service offerings.
• Operationally rigorous, data-driven and outcome-focused.

Our Mission

Octopus Legacy is the place to plan for death and find support after loss. 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, leaving 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. 

Benefits:

• Octopus share incentive scheme.
• 27 days holiday + extra day off for your Birthday.
• Work from anywhere in the world for up to 4 weeks per year.
• Vitality Health & Life Insurance. 
• Pension scheme.
• Enhanced parental leave.
• Free Will & LPAs + discounts on other Octopus services.
• Cycle to Work Scheme and access to the Electric Vehicle (EV) Salary Sacrifice Scheme.
• Octopus Giving: we match any charitable fundraising that you do up to £500. 
• Octopus Springboard: where we help our employees become fully-fledged entrepreneurs.
• Dog friendly office.
• Breakfast every day, snacks and wellness activities.

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

Please note: We’re hiring across multiple locations in England, including Edinburgh, London, Yorkshire, Newcastle, Exeter, Cambridge, and more! To apply, you must have a valid UK driving licence, access to a car, and be willing to travel within your local area for appointments.

The Company

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 are seeking a dedicated Estate Planning Consultant who will be responsible for conducting home visits to assist clients in the process of drafting and creating wills. You will take the time to discuss your clients requirements in detail, explaining how the use of wills, trusts and lasting powers of attorney can work to protect them, their estate and their loved ones. The ideal candidate will excel in providing personalised and comprehensive guidance to individuals and families, ensuring their wishes are accurately documented whilst showing compassion and care.

Key Responsibilities:

• Conduct in-depth consultations during home visits to understand clients' unique needs, assets, and preferences for estate planning
• Guide clients through the legal aspects of will creation, addressing questions and concerns with clarity and expertise
• Collaborate with legal teams and resources to stay informed about current estate planning laws and regulations
• Maintain a meticulous record-keeping system to track client information, preferences, and any legal documentation
• Support with online Wills and other services within the company when required
• Provide exceptional customer service by offering ongoing support and addressing any post-visit inquiries or adjustments
• Stay abreast of industry trends and best practices in estate planning to enhance service delivery

Who Are You?

• Comfortable being fully remote on appointments (opportunity to be in office outside of appointments)
• Must have a full UK driving license and be willing to drive around London
• STEP qualified (preferred)
• Knowledge of how to write Wills and understanding the legalities
• Knowledge of how LPAs work
• In-depth understanding of Octopus Legacy’s services and ability to upsell
• Proficient in identifying indicators of concerns related to clients' testamentary capacity
• High levels of empathy, discretion and care
• Excellent verbal and written communication skills
• Active listening skills and the ability to understand the customer’s needs
• Proactive in initiating tasks independently and effectively following instructions
• Flexible schedule to accommodate home visits based on clients' availability

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.

Benefits:

• Octopus share incentive scheme.
• Flexible holiday + extra day off for your Birthday.
• Vitality Health & Life Insurance. 
• Pension scheme.
• Enhanced parental leave.
• Free Will & LPAs + discounts on other Octopus services.
• Cycle to Work Scheme and access to the Electric Vehicle (EV) Salary Sacrifice Scheme.
• Octopus Giving: we match any charitable fundraising that you do up to £500. 
• Octopus Springboard: where we help our employees become fully-fledged entrepreneurs.

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