Aimed at experienced field sales professionals with a background in high-value B2C sales who are comfortable with sensitive conversations.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Octopus Legacy via Greenhouse
Position: Senior Sales Executive
Location: Field-based (home and virtual appointments)
Start date: ASAP
Commitment: Perm, full-time
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?
Your next move, with more purpose
You don't need a background in law or estate planning to join us. We'll teach you everything you need to know about wills, trusts and lasting powers of attorney. What you do need is a proven track record in field sales: you've sold face-to-face, you've hit your numbers at a business with a high bar, and you know how to earn a client's trust in the first five minutes.
Maybe you've been a field sales executive or BDM at a well-known brand, and you're looking for work that means more. If you're the person clients trust to explain things clearly and do right by them, and you can close, we want to talk to you.
The Role
As a Senior Sales Executive, you'll help families plan for one of life's most important moments. Through home visits and virtual appointments, you'll take people through their options for wills, trusts and lasting powers of attorney, and help them choose the plan that's right for them.
You won't need to find your own leads. Every appointment is booked in for you by our team, with clients who've already asked to speak to us. No cold calling, no prospecting - your time goes on what you do best: sitting with clients and helping them get a plan in place.
This is a sales role, and you'll have targets. But it's never about pushing. Our best consultants win because clients trust them, understand what they're buying and feel genuinely looked after. You'll be the face of Octopus Legacy in our clients' homes, so presence, credibility and judgement matter as much as your close rate. You'll be rewarded for getting that right.
We want to be honest - it won't always be easy. You'll be talking to people about death, family and money, sometimes at difficult moments in their lives. It takes warmth, confidence and resilience. But if you want a role where every conversation counts, this is it.
What You'll Do
Run consultations with clients at home or online, getting to know their family, their wishes and what worries them
Attend appointments booked in for you by our team, making the most of every opportunity in your diary
Explain wills, trusts and lasting powers of attorney in plain, jargon-free terms
Recommend the right products and services for each client, and help them make an informed decision
Follow up with the clients you've met, turning conversations into completed plans
Hit and exceed your targets for conversion and customer satisfaction
Keep accurate, confidential records, so every client's decisions are clearly documented
Work closely with our legal team to make sure every plan meets the right standards
Deliver great aftercare - answering questions and helping clients update their plans as life changes
Who You Are
This opportunity is ideal for:
Experienced field sales executives or BDMs looking to bring their skills to a sector with real purpose
People who've built their career at one or two well-known, respected businesses with a high bar for performance
Strong closers who'd rather spend their time with clients than chasing leads
Anyone who wants structured training in a new sector and a clear path to grow
We're looking for people who:
Have a strong academic background - a degree or equivalent
Have a proven track record in face-to-face, field-based sales, with consistent results against target
Have sold considered, high-value products or services, where clients take time to decide and trust is everything
Are polished, credible and comfortable in any client's home
Are excellent communicators, with strong emotional intelligence
Are motivated by targets and by doing right by the client - and know the two go together
Are confident having sensitive conversations about family, money and death
Are self-motivated and organised, comfortable working independently in the field
Are resilient, with the ability to stay calm and warm when conversations get emotional
Are happy driving within their local area for home appointments
(Bonus but not required) Have some knowledge of wills, trusts or LPAs
Training and Support
You'll start with a structured training programme covering estate planning, our products and how we run a great consultation, building on the sales skills you already have. After that, you'll have ongoing coaching and support from our team and our legal experts, so you're never on your own.
Where Could This Role Take You?
Depending on your performance and interests, you could:
Progress into a senior consultant role
Move into coaching or leading a team of consultants
Explore opportunities across our wider legal, sales or customer teams
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
Competitive base salary plus commission
Octopus share incentive scheme
Flexible holiday + an 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
If you are not 100% sure if you are right for the role, please apply regardless and we will be happy to consider your application.
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.