Head of Customer

Remote Worker LTD.; United States; Hybrid; USD 140,000 - 200,000; Full time

Benefits offered by this job

Hybrid working

Flexible holiday

Work from anywhere (4 weeks/year)

Vitality Health & Life Insurance

Pension scheme

Enhanced parental leave

Free Will & LPAs discounts

EV Salary Sacrifice Scheme

Job summary

Octopus Legacy is redefining estate planning with a high-touch, service-led approach. We are building a leadership team to own the end-to-end customer experience, from first enquiry to renewal, guiding teams with empathy, commercial rigor and scalable processes.

As Head of Customer, you will shape strategy, manage the Customer and Bookings teams, and drive metrics such as conversion, CSAT and retention at scale, while collaborating closely with Sales, Legal, Product and Operations to deliver an

Qualifications

• An experienced leader who has run customer-facing operations in a genuine service business, where relationships develop over time.
• Strong track record of managing managers, building high-performing teams and developing talent.

Responsibilities

• Own the customer strategy and roadmaps for acquisition, service and retention across wills and estate planning.
• Lead the Customer and Bookings teams and their managers to foster a customer-first culture while driving speed and growth.
• Be accountable for conversion, CSAT/NPS, retention and cost to serve with robust reporting for leadership.
• Collaborate with Operations and Product to streamline the customer journey and scale processes and tooling.
• Balance growth targets with compassionate approaches for grieving or vulnerable customers and coach teams accordingly.
• Partner across Sales, Legal, Marketing and Product to ensure a joined-up customer experience.
• Advocate for customers at the leadership table and translate feedback into strategic decisions.

Skills

Leadership

Customer-facing ops

People management

Data literacy

Commercial mindset

Customer obsession

Dashboard interpretation

Job description

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

Our Customer and Bookings teams sit at the heart of the estate planning business unit, guiding people through some of the biggest, most emotionally loaded decisions of their lives, often at life’s toughest moments. As we scale, we need a leader who can turn that frontline into a genuine competitive advantage: fast, warm, commercially sharp, and built to grow.

As Head of Customer, you'll own the end-to-end customer experience across the estate planning business unit, from first enquiry and booking, through advice and delivery, to renewal and referral. You'll lead our Customer and Bookings teams directly, set the strategy for how we serve and convert customers at scale, and be accountable for the metrics that sit at the intersection of customer experience and the P&L: conversion, satisfaction, retention, and cost to serve.

Estate planning is an ongoing, deeply human service, customers need guiding, reassuring and following up with over weeks and months, often at one of the hardest points in their lives. We need someone who's built and run that kind of relationship-driven service function before, and who knows how to combine that with commercial rigour at scale. You'll manage people and managers, partner closely with Sales, Legal, Product and Operations, and report into the General Manager. You'll be given real autonomy to shape how this function works, and real accountability for the numbers it moves.

Your Mission

Key Responsibilities:

• Own the customer strategy: set the vision and roadmap for how we acquire, serve and retain customers across wills, probate and the wider estate planning journey, balancing warmth and trust with commercial rigour.
• Lead the frontline teams: manage and develop the Customer and Bookings teams and their managers, building a culture that puts customers first and where people going above and beyond is normal, all without losing sight of speed, efficiency and growth.
• Drive the metrics that matter: be accountable for conversion, response times, satisfaction (CSAT/NPS), retention and cost to serve, and for building the reporting that makes performance visible to leadership.
• Redesign for scale: work with Operations and Product to remove friction from the customer journey, streamline handoffs between teams, and build processes and tooling that hold up as volumes grow.
• Bridge commercial and human: make the trade-offs between growth targets and doing right by grieving or vulnerable customers, and coach your team to do the same, every day.
• Partner across the business: work closely with Sales, Legal, Marketing and Product to make sure the customer experience is consistent and joined-up from first contact through to delivery and beyond.
• Champion the customer at the top table: represent the voice of the customer in leadership conversations, and make sure decisions elsewhere in the business account for the impact on the people we serve.

Who Are You?

• An experienced leader who has run customer-facing operations in a genuine service business, one where the customer relationship unfolds over time, not a self-serve or SaaS product where the job is done once someone's onboarded. Think professional services, healthcare, financial advice, legal services, or similar high-touch categories.
• Someone who's solved this specific problem before: taking a small, customer function and building it into something senior, structured and reliable. A strong track record of managing managers, building high-performing teams, and developing talent — though we're flexible on exact seniority or title for the right person, provided the depth of experience is real.
• Commercially fluent: you understand how customer experience metrics connect to conversion, retention and the P&L, and you make decisions with both in view.
• Customer-obsessed: you instinctively think about problems from the customers perspective rather than relying on industry norms.
• Comfortable with data: you can read a dashboard, spot what's really going on, and know when to trust a number and when to dig further.
• A natural at operating in a sensitive, high-trust category: you understand that how you say something matters as much as what you say, and you bring that judgement to your team.
• Calm under pressure and comfortable with ambiguity, happy to build processes and structure where none exist yet, and to change course as the business learns.
• A genuinely values-led leader who cares about doing right by people going through one of the hardest moments of their lives, and can hold that alongside a growing, commercial business.

Our Mission

In 2016 Sam’s mum died suddenly in a car accident. The experience that followed was overwhelming - with mountains of paperwork, sitting on hold and navigating financial stress. All at a time when he needed the space to navigate grief.

Death is difficult enough, without everything else that comes with it. Octopus Legacy was created to make the experience of losing someone easier for those left behind - so that they can focus on what matters.

Since then we have helped over 700,000 people plan for death and find support after a loss and are now the second largest estate planner in the UK.

When people think about planning for death they think about wills, life insurance and funerals. These small but mighty acts make a huge difference to the people we love. But why stop there?

We take these cold processes and turn them into something more human. We help customers share more than just money. Encouraging them to leave voice notes, music, recipes. So they can shape a legacy that connects them with the people they love while they’re here. And after they’re gone.

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.