Sales Development Representative

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?

As a Sales Development Representative (SDR) at Octopus Legacy, you’ll be the engine behind our growth. This is a fully outbound, phone-based role – your job is to pick up the phone, open doors, and book meetings that move the business forward.

You’ll work on a rolling set of outbound projects across the business – from partnerships and B2B distribution to new product launches and other commercial initiatives as they come up. No two weeks look quite the same.

We want to be honest – outbound is hard. You’ll hear “not interested” a lot, and the wins come to people who stay consistent when it’s uncomfortable. But if you get energy from the phone, love a target, and want to learn B2B sales from the ground up - this role can be seriously rewarding.

At Octopus Legacy, how we work matters as much as what we do. As one of our founding SDRs, you’ll join at a pivotal time and help shape the outbound playbook from day one.

• Make high-volume outbound calls to book qualified meetings for the commercial team.
• Pick up outbound projects across the business as they come up (partnerships, B2B distribution, new launches and other commercial initiatives).
• Hit and exceed weekly targets for calls, conversations and meetings booked.
• Keep the CRM clean and accurate after every call.

• A natural starter of conversations - comfortable picking up the phone to a stranger and making them glad you did.
• Some experience in outbound sales, SDR/BDR, business development, recruitment, or another target-driven role is a plus - but attitude and work ethic matter more than years on a CV.
• Commercially sharp and target-driven, with genuine hunger to hit and exceed numbers.
• Resilient and consistent – you can take a “no” on call 20 and still bring energy to call 21.
• Organised and methodical, with the discipline to plan your week, work your lists and keep activity high.
• Curious and commercially minded – you enjoy understanding how different businesses make money and where we can add value.
• Confident using CRM tools (HubSpot, Salesforce or similar) and outbound tech.
• A team player who shares what’s working, learns fast, and celebrates other people’s wins.
• (Bonus, not required) Exposure to legal services, financial services, wills/probate, funeral or bereavement sectors, or B2B partnerships.

• 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.
• Clear progression paths into Account Executive, Partnerships and wider commercial roles.
• Competitive base salary + commission, great benefits and opportunities to progress.

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.

• 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.