Head of Owner Success
Location: Chester, with UK-wide travel
Salary: Up to £80,000 + Annual Bonus + Excellent Benefits
Reporting to: Portfolio Director
About Us
Sykes Holiday Cottages is a business with big dreams and bold ambition. With over 30 years of industry experience, over 15 regional brands, and more than 23,000 holiday homes across the UK and Ireland, we’ve become one of the UK’s fastest-growing holiday let agencies.
What started as a family-run business has grown into a vibrant team of passionate people delivering exceptional experiences for guests and property owners alike.
Part of Forge Holiday Group, we’re building a culture where ambition, creativity and collaboration thrive.
We value diversity and inclusion and encourage everyone to bring their authentic self to work. Need adjustments during the recruitment process? Just ask — we’re happy to help.
About the Role
We’re looking for an experienced and commercially focused Head of Owner Success to lead and shape our owner proposition.
Reporting to the Portfolio Director, you’ll take ownership of the Owner Success strategy, leading a national, multi-layered team across Sykes based in Chester and our Regional Brands. You'll use data, owner insight and AI-powered tools to drive growth, improve retention and deliver exceptional owner experiences.
This is a senior role with regular UK travel and the opportunity to influence strategy and drive performance at the highest level.
What You'll Be Doing
Lead and develop high-performing teams across Owner Success and Property Services
Shape and deliver the long-term Owner Success strategy
Own key performance metrics including, Portfolio Growth, Owner Retention, NPS and P&L performance
Build strong relationships with key and strategic property owners
- ️ Drive operational excellence and collaborate across Commercial, Marketing, Technology and Operations
✈️ Represent Sykes across the UK through owner engagement, regional visits and industry events
What We're Looking For
We’re looking for a strategic and commercially minded leader who combines big-picture thinking with operational excellence and has the credibility to influence at senior level.
You’ll bring:
✅ Significant experience in a senior leadership role within Owner Success, Customer Success, Account Management, or a related field
✅ Experience within the holiday, travel, property management, marketplace, or a similar customer-focused sector would be highly advantageous
✅ A proven track record of building, leading and scaling high-performing teams, with experience developing talent and driving a strong performance culture
✅ Strong analytical capability and experience using data, insights and performance metrics to drive decision-making and improve outcomes
✅ Exceptional communication and influencing skills, with confidence engaging and building alignment across senior stakeholders and executive teams
✅ Experience operating with a strong commercial mindset in an operational environment, balancing customer outcomes with business performance
✅ Confidence presenting and influencing at leadership and board level
✅ A willingness to travel regularly across the UK
Our Benefits
✈️ 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
✨ Join us and help shape the future of Owner Success at Sykes Holiday Cottages.
Apply today.
