Head of Winter Events & Trails

Posted 2 Days Ago
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Gloucester, Gloucestershire, England, GBR
Hybrid
Senior level
Events • Food • Payments • Hospitality
The Role
Leads the strategic, commercial, and operational development of winter light trails and live entertainment events. Oversees event teams, partner relationships, planning, delivery, budgets, settlements, guest experience, F&B operations, and continuous improvement. Drives account growth, new event opportunities, service expansion, stakeholder management, and team development across multi-day, multi-location events.
Summary Generated by Built In
The Head of Winter Events & Trails is responsible for driving the strategic, commercial and operational development of Freemans Event Partners’ (FEP) partnership with leading light trail production organisations, ensuring that every event strengthens the relationship and supports long-term growth.
The role oversees the planning, delivery and performance of all seasonal light trail and entertainment projects, ensuring exceptional guest experience, operational quality and commercial success.
Beyond operational excellence, the Head of Winter Events & Trails is responsible for identifying expansion opportunities, influencing future planning with key clients, and positioning FEP as their preferred F&B and event services partner for future projects.
This is a growth-focused role that blends strategic leadership, partner management, operational delivery and team development, ensuring FEP continues to innovate, evolve and expand within the existing client portfolio.
Job Requirements
Essential
  • Senior leadership experience in festivals, concerts, live entertainment or large-scale event operations - with particular focus on multi-day multi-location events.
  • Proven track record in managing high-profile partners and growing strategic accounts
  • Demonstrated success in leading multidisciplinary event teams
  • Strong commercial acumen with experience in budget oversight, commercial models or settlements
  • Experience in high-pressure, fast-paced live-event environments
  • Strong communication, influencing and stakeholder management skills
Desirable
  • Understanding of promoter relationships, production environments and live-event industry dynamics
  • Experience expanding service offerings or growing commercial partnerships
  • Knowledge of festival infrastructure, site operations or backstage management
  • Experience introducing innovation or new service models to live events

Job Responsibilities
Strategic Leadership & Partnership Growth
  • Lead the long-term strategic direction of the FEP / Client partnership
  • Maximise commercial and operational opportunities within the client portfolio
  • Influence future planning and event strategy with client leadership
  • Identify opportunities for new event activity, expanded services or new revenue streams
  • Ensure every event strengthens the partnership and contributes to long-term growth
Leadership of Event Teams
  • Lead, coach and develop Event Managers delivering light trail events
  • Set clear performance standards, KPIs and delivery expectations
  • Build a culture of creativity, innovation and high performance
  • Ensure consistent delivery across all festivals, concerts and multi-day live entertainment events
Business Development & Opportunity Expansion
  • Work closely with the core senior colleagues (incl. Projects, Operations and Business Development) to:
    • Secure new live events
    • Expand FEP’s service offerings
    • Win additional projects or venues under the client umbrella
  • Represent FEP as the senior operational leader in commercial and strategic discussions
  • Build strong relationships with promoters, production leads and potential event partners
Operational Excellence
  • Ensure exceptional planning, readiness and delivery across all winter trail events
  • Maintain consistently high standards across F&B, concessions, bars and guest experience
  • Support onsite troubleshooting and escalation management
  • Implement best practice and drive continuous improvement in event delivery
Commercial & Financial Management
  • Support the commercial performance of winter trail events, including budgets, forecasting and settlements
  • Identify commercial risks and opportunities to enhance profitability
  • Ensure service delivery meets or exceeds commercial expectations
Stakeholder & Partner Management
  • Act as the senior FEP representative to client’s leadership
  • Build strong, trust-based relationships with promoters, production stakeholders and suppliers
  • Ensure client’s expectations are understood, managed and consistently exceeded
  • Provide proactive insights, solutions and recommendations
Cross-Divisional Collaboration
  • Work closely with Food Service, Bars, Catering, Concessions, Operations, Brand Partnerships, Marketing and FEP PAY
  • Ensure seamless alignment across planning, delivery and review phases
  • Support organisational initiatives that enhance delivery quality and commercial performance
People Leadership & Development
  • Lead the development and progression of Event Managers operating within the client portfolio
  • Provide coaching, mentoring and performance feedback
  • Support recruitment, succession planning and seasonal resource management
  • Foster a cohesive, engaged and motivated team culture
Innovation & Continuous Improvement
  • Identify opportunities for innovation in technology, service, food operations or audience engagement
  • Lead post-event reviews, embedding lessons learned into future planning
  • Drive continuous improvement projects across all light trail events

Benefits
  • Competitive salary, commensurate with experience.
  • Bonus scheme 
  • 25 days’ annual leave plus bank holidays.
  • Pension scheme.
  • Access to FEP’s wider employee benefits programme.
  • A dynamic, fast-paced environment where you can make a genuine impact at some of the UK’s most exciting venues.

Skills Required

  • Senior leadership experience in festivals, concerts, live entertainment, or large-scale event operations, particularly multi-day, multi-location events
  • Proven track record managing high-profile partners and growing strategic accounts
  • Demonstrated success leading multidisciplinary event teams
  • Strong commercial acumen, including budget oversight, commercial models, or settlements
  • Experience working in high-pressure, fast-paced live-event environments
  • Strong communication, influencing, and stakeholder management skills
  • Understanding of promoter relationships, production environments, and live-event industry dynamics
  • Experience expanding service offerings or growing commercial partnerships
  • Knowledge of festival infrastructure, site operations, or backstage management
  • Experience introducing innovation or new service models to live events
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The Company
HQ: Stroud
367 Employees
Year Founded: 1975

What We Do

Freemans Event Partners is a family-owned, multi-service event provider established in the United Kingdom. It partners with major European events, venues, and brands to enhance fan and spectator experiences. Its offering includes bespoke food and beverage operations, event infrastructure and logistics, cashless and PCI-compliant payment services, commercial brand partnerships, immersive activations, and on-site event management across sporting, cultural, and entertainment occasions.

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