About Us

Chief of Staff

Full-time, London, UK (Hybrid)

The Company

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, 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.

The Role

As the Chief of Staff, you will be instrumental in driving operational efficiency, fostering cross-functional collaboration, and serving as a key liaison between senior leadership and various departments while taking direct ownership of one of our critical growth channels. Reporting directly to the CEO, you will play a pivotal role in shaping the company's trajectory.

This is a great opportunity for someone looking to work in a fast-paced and changing environment, who likes to work autonomously, enjoys a challenge and wants to make an impact!

Key Responsibilities

  • Operational Execution: Execute and streamline operational processes to enhance efficiency and effectiveness across the organisation.
  • Strategic Initiatives: Lead and execute key strategic projects, ensuring alignment with organisational goals and driving successful outcomes.
  • Stakeholder Management: Serve as a liaison between the executive team, department heads, and external partners, facilitating clear communication and fostering strong relationships.
  • Cross-functional Collaboration: Facilitate collaboration between different teams, ensuring seamless execution of projects and initiatives.
  • Executive Support: Provide high-level support to the CEO, including meeting preparation, and ad hoc tasks to optimise their productivity.
  • Research and Analysis: Conduct market research, competitor analysis, and industry assessments to inform strategic decision-making.
  • Special Projects: Lead and oversee special projects as directed by the CEO, leveraging your analytical and problem-solving skills.

Who Are You?

You want to work at a startup and you’ll thrive in a fast paced environment. You have a personal growth mentality, with a hunger to learn. Autonomy doesn't scare you, and being self-sufficient and happy to come up with solutions to problems on your own is attractive to you.

  • 5-10 years experience.
  • Proven experience in a similar Chief of Staff or consultancy role.
  • Strong entrepreneurial spirit with a willingness to explore innovative solutions and contribute to the growth and success of the team.
  • Exceptional project management and organisational skills.
  • Strong analytical and problem-solving abilities.
  • Excellent interpersonal and communication skills.
  • Ability to work autonomously and handle confidential information with discretion.
  • Previous experience in a startup or smaller company is an advantage.
  • Self-motivated, with a strong work ethic and a commitment to continuous improvement.


  • Flexible working: 3 days in the office (London, Holborn) you can work remotely up to 2 days a week. You are also able to work from anywhere in the world for up to 4 weeks per year.
  • Life insurance, health insurance, will & lasting power of attorney.
  • An extra holiday day for your birthday.
  • Octopus share incentive scheme 2024+: You can invest up to £150 a month from your gross salary (i.e. pre tax) into the Octopus Group, and for every share you buy Octopus will grant you an additional 1.5 shares at no charge.
  • Cycle to Work Scheme: to help lower your carbon footprint whilst being good for your health. We also have access to the Electric Vehicle (EV) Salary Sacrifice Scheme.
  • Octopus Giving: our charitable foundation is dedicated to helping those charities that are making the world a better place, we match any charitable fundraising that you do up to £500.
  • Octopus Springboard: where we help our employees become fully-fledged entrepreneurs.

If you're not 100% sure that you are right for the role, please apply anyway. What's the worst that could happen?

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.

Start Date: Immediate

Commitment: Full time

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We’re tackling some of the biggest taboos surrounding death. Together, we can help to make some of the toughest times in people’s lives easier.

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