General Manager - Estate Planning

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

The General Manager will work alongside 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.

The role carries full end-to-end accountability for the unit’s performance, growth and transformation. You 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  sustainable profitability.

You’ll guide the organisation through a period of rapid growth and increasing complexity, strengthening operational foundations, embedding scalable systems and processes, and taking full P&L ownership. Working closely with the CEO, founder, and executive team, you’ll play a key role in shaping the future direction of both the business unit and Octopus Legacy as a whole.

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, brand, 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

• Deliver strong, sustained revenue growth, with consistent YoY growth exceeding 50%.
• Improve profitability and operating efficiency, reducing cost-to-serve and turnaround times while maintaining exceptional customer outcomes.
• Embed a clear, data-driven operating cadence, with strong performance visibility, accountability, and disciplined execution across the business.
• Launch and scale new products and service enhancements that drive measurable commercial and customer impact.
• Build a high-performing, resilient organisation, retaining top talent and strengthening leadership depth across the business unit.

Who Are You?

• Proven track record leading and scaling high-growth, service-led or tech-enabled businesses, with full ownership of commercial and operational performance.
• Strong commercial and financial acumen, with experience managing budgets, forecasting, and performance in a P&L-driven environment.
• Highly structured and data-driven, able to bring clarity, pace, and execution to complex or ambiguous challenges.
• Experienced in building scalable systems, processes, and teams to support rapid growth.
• Strong leadership presence, with the ability to set high standards, build trust, and drive accountability at every level.
• Technology-minded, with a clear view of how systems, automation, and product evolution enable scale.
• High ownership, pace, and integrity, with the judgement to operate effectively in a regulated environment.

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 opportunity employer.