Sales Training Manager

Location: London / Hybrid / Remote (UK)
Team: Estate Planning
Employment Type: Full-Time

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…). We have a mission - to transform how people plan for the future and support families through some of life’s most important and sensitive moments.

We’re scaling fast and reimagining a sector that’s long resisted change. To get there, we’re building a team of top performers who care deeply about people, learning, and doing work that matters. Ready to help shape a category from the ground up?

As our Sales Training Manager (Estate Planning), you’ll shape the performance, capability, and culture of our Estate Planning Consultant (EPC) teams. You’ll design and deliver training that builds confidence, emotional intelligence, deep product understanding, and consultative sales skills - helping consultants support clients through meaningful, often personal conversations.

You’ll partner closely with EPC Leadership, Product, and Operations to create a world-class onboarding and development experience, ensuring every consultant is set up to deliver excellent customer outcomes and commercial performance in an environment that is as human as it is strategic.

This is a unique opportunity to bring best-in-class sales coaching and training expertise from financial services or other regulated, customer-centric environments into a category that needs fresh thinking.

• Creating, delivering and coordinating training programmes for new EPC cohorts taking our ‘training academy’. This focuses on customer relationships, sales performance and technical knowledge of estate planning. 
• Responsible for ongoing development of EPC team, via 1:1 coaching and mentoring and continuous performance reviews as they transition in their role outside of the academy. Including consultative sales skills, product knowledge, soft-skills mastery, compliance, and estate-planning fundamentals.
• Holding regular training and feedback sessions with regional managers, to help support and train consultants within the field and keeping everyone up to date with any changes that may affect estate planning.
• Work with Estate Planning Leadership, Legal, Product, and Operations to ensure content is accurate, current, and aligned to business goals and regulatory expectations.
• Measure training effectiveness, identify capability gaps, and iterate on curriculum to continuously raise standards.
• Support the hiring process through skills assessments, role-plays, and insight-driven evaluation.
• Champion Octopus Legacy’s mission-led, high-ownership culture by building learning experiences that empower people to grow and succeed.
  

• An experienced trainer or sales coach from a regulated or customer-centric environment (e.g., estate planning, financial services, insurance, wealth management, mortgages, or similar).
• Skilled in consultative selling, coaching frameworks, and translating complex or sensitive topics into engaging learning experiences.
• An exceptional communicator with high EQ - able to help consultants build trust and confidence with clients.
• Highly organised, comfortable working at pace, and able to manage multiple priorities in a fast-moving scaling business.
• Able to deliver engaging training in person and virtually.
• Passionate about helping people develop, and excited by our mission to humanise estate planning.
• Knowledge of estate planning is beneficial, but not essential - a strong willingness to learn quickly is far more important.
  

We want you to feel supported, empowered, and truly excited to be part of the team. Our benefits include:

• Share Incentive Scheme (SIP) - invest in the company’s success.
• Vitality Health & Life Insurance, plus access to a free Will and Lasting Powers of Attorney.
• Pension scheme to support long-term financial wellbeing.
• Enhanced parental leave for growing families.
• Cycle to Work Scheme and Electric Vehicle Salary Sacrifice Scheme.
• Charity matching (up to £500) and volunteer days.
• Octopus Springboard - cash funding and time to explore entrepreneurial ideas.
• Birthdays off - because life should be celebrated.
• Company events, socials, snacks, and a dog-friendly office.
  

• Consultants consistently delivering high-quality client conversations, driving strong customer outcomes and commercial performance.
• A scalable and robust training infrastructure that evolves with the business.
• A culture where learning, feedback, and continuous improvement are woven into everyday life.
• Consultants who feel confident, capable, supported - and proud of the work they do.
  

At Octopus Legacy, you’ll work with people who care deeply about their impact. We offer a collaborative, high-ownership environment where you can grow professionally while shaping an emerging category. You’ll help make difficult conversations easier and empower people to plan confidently for the future.