About Us

Gambit Holdings is a growing group of businesses operating across insurance, marketing, recruitment, and community-led initiatives.

In this role, you will support the wider group, including:

Gambit Partners - a sales, marketing, and growth consultancy
Gambit Insurance Solutions & Mode Insurance - modern insurance businesses supporting charities, freelancers, and growing businesses
iCAN - one of the UK insurance industry’s leading diversity and inclusion platforms

We are a fast-moving and entrepreneurial business group focused on growth, partnerships, innovation, and creating meaningful impact across the industries we work in.

Job overview

As the Executive Assistant, you will play a key role in supporting the leadership and operations of Gambit Holdings.

This is a high-impact role combining executive support, operational coordination, administration, and project support across multiple businesses and stakeholders.

Working closely with the Founder and the wider leadership team, you will help keep priorities aligned, operations organised and key business activities moving forward.

This role would suit someone who thrives in a fast-paced environment, enjoys solving problems and takes pride in creating structure, organisation and efficiency.

We are looking for someone proactive, dependable, and excited to become a trusted part of a growing business group.

Key responsibilities

Executive Support

Provide proactive support to senior leadership across the group
Manage busy diaries, scheduling, meetings, travel, and priorities
Help keep projects, actions, and communications organised and moving forward
Prepare documents, presentations, and meeting materials where required

Business Support

Support the smooth day-to-day running of the business across multiple teams
Assist with invoicing, administration, reporting, and operational processes
Maintain accurate records, systems, and internal coordination
Identify opportunities to improve organisation, efficiency, and workflows

Projects & Coordination

Act as a central point of coordination across the group
Support team organisation, scheduling, and project visibility
Assist with internal projects, research, and business initiatives
Support CRM management, data handling, and administrative processes

Events & Stakeholder Support

Support the planning and delivery of events, meetings, and business activities
Assist with logistics, communications, and stakeholder coordination
Provide occasional support at external events and networking activities

Knowledge, skills and abilities

The core skills expected for this role:

Exceptional organisation and attention to detail
Strong time management and ability to prioritise effectively to meet deadlines
Excellent written and verbal communication skills
Proactive mindset with the confidence to take ownership
Ability to manage multiple stakeholders and projects simultaneously
High level of professionalism, discretion, and reliability
Comfortable working in a fast-paced and evolving environment

Experience required

Previous experience in an Executive Assistant, Operations, Project Coordination, or similar role
Experience supporting senior leadership, founders, or fast-moving teams
Strong experience managing diaries, administration, and operational workflows
Confidence working across multiple teams, projects, and priorities
Familiarity with CRM systems, project management tools, and operational reporting
Experience supporting events, projects, or business operations would be beneficial

What is on offer?

Competitive salary
Flexible remote working with occasional in-person collaboration and events
Minimum of 27 days holiday + bank holiday, with additional opportunities for paid time off (pro rata from Jan-Dec)
Annual team events and team building days
3 months’ notice period
Pension Scheme – post probation, eligibility to join the group pension scheme, totalling 9% with an employer pension contribution of 6% and employee contribution on a salary sacrifice basis provided you contribute at least 3%
Access to the “Employee Perks” programme, offering discounts and rewards
Opportunity to grow alongside an ambitious and expanding business group

Additional requirements

Occasional travel across the UK may be required to support events and team activities
Flexibility to adapt responsibilities as the role evolves
Willingness to take ownership and contribute to continuous improvement across the business

Why this role is different

This is not a traditional Executive Assistant role.

You will become a trusted operational partner across a growing group of businesses, helping leadership operate effectively, improving operational efficiency, and supporting projects that directly contribute to business growth.

We are looking for someone who enjoys taking ownership, solving problems, and becoming a trusted part of a fast-moving entrepreneurial business.

iCAN jobs

Executive Assistant (Group Role)