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Head of Onboarding

United Kingdom, Chester Employment contract 70000.00 - 80000.00 GBP / Year · Job Posted June 29, 2026
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Job Description

Lead the future of owner onboarding at Sykes Holiday Cottages. At Sykes Holiday Cottages, we're on an exciting journey to transform how holiday homeowners join our brands and achieve success from day one. We're looking for an experienced Head of Onboarding to lead this transformation, creating a seamless, high-performing onboarding experience that accelerates growth, maximises conversions and delivers exceptional owner experiences. This is a pivotal leadership role where you'll shape the end-to-end onboarding strategy, leading teams across our Chester headquarters and our nationwide field consultants. You'll combine commercial thinking, operational excellence and customer obsession to ensure new owners realise value faster than ever before.

Job Responsibility

  • Lead and inspire a high-performing onboarding function, creating a culture of accountability, pace and continuous improvement
  • Own the end-to-end owner onboarding journey, from enquiry through to go-live and first booking
  • Drive improvements in lead conversion, onboarding efficiency and time to value
  • Partner closely with Marketing, Commercial, Product and Technology teams to remove friction and optimise every stage of the onboarding journey
  • Develop tailored onboarding experiences for individual owners and multi-unit partners
  • Support the growth of our Multi-Unit Site proposition alongside our Business Development Managers
  • Use insight and performance data to identify opportunities, improve processes and influence strategic decisions
  • Own onboarding KPIs including conversion, speed to market, owner satisfaction and early-stage commercial performance

Requirements

  • Significant leadership experience within onboarding, commercial operations, customer lifecycle or operational leadership
  • A proven track record of improving conversion, reducing operational cycle times and driving measurable business growth
  • Strong commercial awareness with the ability to translate operational performance into business success
  • Exceptional leadership skills with experience developing high-performing teams
  • Excellent stakeholder management, with the confidence to influence at senior level
  • Strong analytical capability, using insight and data to improve performance
  • A collaborative leadership style and a passion for continuous improvement

Nice to have

Experience within travel, property, marketplaces, e-commerce or digital platforms

What we offer

  • 33 days holiday + up to 5 extra with long service
  • Buy additional holiday
  • Birthday off
  • 2 volunteering days
  • Enhanced parental leave
  • Pension contributions
  • Discounted stays at Forest Holidays & Sykes Cottages
  • Health cash plan & life assurance
  • Training & development opportunities
  • 24/7 mental health support
  • On-site gym & parking at Chester HQ
  • Employee savings scheme
  • Long service awards & company events

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