Customer Success Specialist

This is a full-time, office-based role with plenty of variety. You’ll work Monday to Friday on set shift patterns, which may vary occasionally, including early starts or later finishes, though never beyond 7pm.

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 Customer Success Specialist at Octopus Legacy (internally known as ‘Legacy Specialist’), you’ll guide people through some of the most meaningful decisions of their lives - and help them feel calm, confident and supported at every step.

You’ll be the first voice our customers hear, the trusted advisor who explains their options clearly, and the problem-solver who ensures everything runs smoothly from the very first conversation to the final document. You’ll blend empathy with commercial awareness: supporting people during emotional moments while helping them choose the services that genuinely meet their needs.

We want to be honest -  it won’t be easy. You’ll be speaking to people at difficult and emotional moments in their lives, often when they need guidance and reassurance the most. You’ll sometimes deal with complexity, high emotion, and situations where you’re holding space for someone who really needs support.

It takes resilience, calm under pressure, and the ability to stay warm and clear even when conversations are tough. But if you’re someone who finds purpose in helping people when it matters most - and you thrive in a fast-paced, high-ownership environment - this role can be incredibly rewarding.

You’ll have the freedom to be human - no scripts, no robotic call targets. With the right tools, trust, and training, you’ll take full ownership of the customer journey and spot opportunities to add value.

At Octopus Legacy, how we work matters as much as what we do. As part of our founding Customer Success team, you’ll join at a pivotal time - helping us scale, shape the way we work, and deliver the best possible experience for our customers.

Our values are simple: Customer-First. Work hard. Stay optimistic.

Key Responsibilities:

• Be the first point of contact for customers via phone, email, and chat - guiding them with clarity, warmth, and confidence.
• Understand customer needs and recommend the right estate planning products and services.
• Lead consultations, explain options clearly, and help customers make informed decisions.
• Own the customer journey end-to-end - from initial enquiry to booking and document delivery - ensuring a seamless experience.
• Hit and exceed personal and team targets for engagement, conversion, and customer satisfaction.
• Keep accurate and confidential customer records.
• Share insights and ideas to improve processes, resources, and the overall customer experience.
• Collaborate across teams to drive efficiency and elevate service.
• Bring energy, initiative, and a problem-solving mindset to help the team grow and succeed.

Who Are You?

• A compassionate communicator who builds trust easily - especially when conversations are tough.
• Experience in sales, customer service, estate planning or other advisory roles.
• Target-driven and commercially aware, with a desire to help customers choose what’s right for them.
• Resilient and adaptable, with an ability to stay calm in high-pressure situations.
• Organised, attentive to detail, and comfortable managing multiple priorities.
• Proactive and solutions-focused, always thinking about how to make things better.
• Confident using CRM tools and technology.
• A team player who leads with kindness and genuinely cares about doing meaningful work.

Why You’ll Love It Here

• We’re part of a group that believes work should mean something. You’ll be trusted to do what’s right, supported to grow, and encouraged to share your ideas and shape the way we work.
• You’ll be part of a team you can truly count on - colleagues who support each other and always put customers first, every day and at every step of your journey.
• A fast-growing business with room to learn, grow and influence change.
• Plenty of opportunities to learn, develop your skills and make a real impact.
• Competitive commission structure, great benefits and opportunities to progress.

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.