Workplace Strategy and Proposition Lead

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We’re looking for someone exceptional to shape, own and evolve our Workplace proposition for HR and Reward teams - defining the strategy, proposition, pricing, materials, training, and communication engine that powers one of the most important parts of Octopus Money.

Workplace is our most mature channel, trusted by employers to provide financial wellbeing to tens of thousands of employees. But expectations are rising. HR and Reward leaders want clarity, value, and outcomes - and we need someone who can keep us ahead of the curve.

About Octopus Money

At Octopus Money, we’re on a mission to make money advice accessible to all – because the right advice can turn your life dreams into reality.

The facts are alarming: half of Brits reach retirement age without enough money to live the life they want, financial stress is a leading cause of poor mental health and only 8% of us have access to 1-to-1 advice.

There’s plenty of information out there, but most of us just wish that someone we trust would tell us what to do with our money!

With Octopus, you get a personalised plan and a friendly expert to help you make it happen. We combine advisers, coaches and technology to understand your situation and recommend the right steps for your savings, investments, pensions and more. Then, we make it easy to invest in a custom portfolio, managed by experts.

We believe everyone deserves personal, 1-to-1 advice with their money.

What the role is about

This person will be the strategic lead and internal expert of our Workplace proposition. They’ll design how it works, evolve it with insight from HR/Reward buyers, and enable sales and delivery teams to scale it.

They’ll:

Shape and evolve the proposition

• Own the full Workplace strategy across pricing, positioning and commercial model.
• Gather insight from HR/Reward leaders, sales, success, planners, coaches, advisers and operations to continuously evolve the proposition.
• Turn feedback into clear decisions: what we offer, how it works, what it costs, and how it delivers value.

Build and communicate a clear narrative

• Create simple, compelling messaging that resonates with HR/Reward buyers.
• Build all proposition artefacts - decks, one-pagers, Q&A, scripts, objection handling, FAQs and internal briefs.
• Work closely with marketing to package the proposition in a way that cuts through.

Enable sales and success teams

• Train sales and account managers to tell the story confidently and consistently.
• Run regular enablement sessions and ensure the field always has the latest materials.
• Create exemplar client journeys, demo scripts, and use cases that bring the proposition to life.

Support scale and delivery

• Ensure the Workplace proposition is designed to be delivered repeatedly and consistently.
• Provide clarity to planning, coaching and success teams about what we promise - and how to deliver it.
• Work cross-functionally to refine employee journeys, hand-offs, and referral pathways.

Be the internal point of truth

• Act as the SME for anything related to Workplace strategy, pricing, and proposition.
• Translate complexity into clarity for colleagues and clients.
  Stay on top of HR/Reward market trends and use them to inform the evolution of the product.

The experience you’ll bring:

We’re looking for someone commercially sharp, strategically strong and deeply comfortable working with HR/Reward leaders. You should thrive in a role that blends proposition design, commercial thinking, field enablement, and cross-functional leadership.

Likely backgrounds include:

• HR/Reward consulting, employee benefits advisory, or workplace wellbeing providers
• Commercial or strategy roles within employee benefits, fintech, or SaaS businesses
• Sales or account management roles selling into HR/Reward, particularly with experience shaping propositions
• Marketing or proposition leadership roles in benefits, pensions, financial wellbeing or similar

You’re likely someone who:

• Can create clarity where none exists
• Is comfortable gathering input from all sides of the business
• Can translate qualitative feedback into strategic decisions
• Communicates simply and effectively
• Enjoys enabling others to be brilliant
• Balances strategic thinking with hands-on execution

In return for your contribution, we offer a base salary of £85,000-100,00 DOE + benefits.

Please note, as a regulated business we are required to run background checks for all employees which covers adverse financial and unspent convictions. These will only take place upon a successful job offer.

About Octopus Group
Octopus is a group of companies which invests in the people, ideas and industries that will help to change the world. We collectively believe that the companies serving two of our most important needs – our financial wellbeing and our planet’s future – are failing. And we want that to change. We want everything we do, whether that’s in financial services or energy supply, to have a positive impact on the people it touches. The energy supply business - Octopus Energy is the #1 rated UK energy supply business, and the only one to be recommended by Which? three years in a row.

Perks & Benefits

Make a difference
We're on a mission to help millions of people improve their finances. Seeing the impact we can make on our client's lives is deeply rewarding, and motivates the whole team to keep doing more to improve our service. Our client feedback is extremely positive, with a rating of 4.8 out of 5 on Vouchedfor.

Flexible working
We currently operate a hybrid model which is a mix of office and remote. You'll have the option of working from home 2 days per week (Monday and Friday) with the remainder from our central London office in Holborn.

Work from anywhere
We give an 18 day work from anywhere allowance to swap out the on site days or take some time working from another country. NB - Due to compliance regulations this does not apply to individuals that give regulated financial advice.

Join a great team
We're a diverse team with decades of experience in financial services and a proven track record. We believe in treating everyone with transparency and respect.

Rapidly grow your career
We believe in hiring people who are better than us, and giving them opportunities to achieve great things. As we continue to scale up, there will be opportunities for ambitious new joiners to demonstrate their skills and take on bigger roles.

Share incentive plan and team bonus
Being part of Octopus we benefit from the group share incentive plan. In addition, for those who are not commission based we offer a team bonus provided we meet our team goals.

Pension, enhanced parental leave, private medical insurance & other perks
As an Octopus Money employee you'll get access to a company pension, enhanced parental leave, PMI, day off for your birthday and other benefits to make sure you're healthy and happy, now and in the future! 

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We believe in equal financial education for everybody, no matter their background.  We pride ourselves on building an inclusive working environment where diversity is celebrated.

We do not and never will discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

If you require support completing your application please contact Luke Stepney, Head of Talent at applications@octopusmoney.com