At a Glance
- Tasks: Lead and develop high-performing teams to enhance owner experiences and drive growth.
- Company: Join Sykes Holiday Cottages, a vibrant team with over 30 years of industry experience.
- Benefits: Enjoy 33 days holiday, enhanced parental leave, and health cash plans.
- Other info: Dynamic role with UK travel and excellent career development opportunities.
- Why this job: Shape the future of Owner Success and influence strategy at a senior level.
- Qualifications: Proven leadership experience in Owner Success or related fields is essential.
The predicted salary is between 80000 - 80000 £ per year.
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.
Head of Owner Success employer: Sykes Cottages
Sykes Holiday Cottages is an exceptional employer that fosters a vibrant and inclusive work culture, where ambition and creativity are celebrated. Located in Chester, with opportunities for UK-wide travel, employees benefit from a comprehensive package including generous holiday allowances, enhanced parental leave, and ongoing training and development. Join a passionate team dedicated to delivering outstanding experiences for property owners and guests alike, while enjoying unique perks such as discounted stays and 24/7 mental health support.
StudySmarter Expert Advice🤫
We think this is how you could land Head of Owner Success
✨Tip Number 1
Network like a pro! Get out there and connect with people in the industry. Attend events, join relevant groups on social media, and don’t be shy to reach out to potential colleagues or mentors. You never know who might have the inside scoop on job openings!
✨Tip Number 2
Prepare for interviews by researching the company and its culture. Understand their values and how they align with your own. This will help you tailor your responses and show that you’re genuinely interested in being part of the team at Sykes Holiday Cottages.
✨Tip Number 3
Practice your pitch! Be ready to explain how your experience in Owner Success can drive growth and improve retention. Highlight your leadership skills and how you’ve built high-performing teams in the past. Confidence is key!
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets seen. Plus, it shows you’re serious about joining our vibrant team at Sykes. Let’s make those big dreams happen together!
We think you need these skills to ace Head of Owner Success
Some tips for your application 🫡
Tailor Your CV:Make sure your CV reflects the skills and experiences that align with the Head of Owner Success role. Highlight your leadership experience and any relevant metrics you've achieved in previous roles to show us what you can bring to the table.
Craft a Compelling Cover Letter:Your cover letter is your chance to tell us why you're the perfect fit for this position. Share your passion for owner success and how your strategic mindset can help shape our future. Be authentic and let your personality shine through!
Showcase Your Data Skills:Since this role involves using data to drive decisions, make sure to mention any analytical tools or methodologies you’ve used in the past. We want to see how you’ve leveraged insights to improve outcomes and drive performance.
Apply Through Our Website:We encourage you to apply directly through our website. It’s the best way for us to receive your application and ensures you’re considered for the role. Plus, it shows us you’re keen on joining our team at Sykes Holiday Cottages!
How to prepare for a job interview at Sykes Cottages
✨Know Your Numbers
As a Head of Owner Success, you'll need to be comfortable with key performance metrics like Portfolio Growth and NPS. Brush up on these numbers before your interview, and be ready to discuss how you've used data to drive success in previous roles.
✨Showcase Your Leadership Style
This role requires leading high-performing teams, so think about your leadership style and be prepared to share examples of how you've developed talent and fostered a strong performance culture. Highlight specific instances where your approach made a difference.
✨Build Relationships
Since the job involves engaging with property owners and stakeholders, demonstrate your relationship-building skills. Share stories that illustrate how you've successfully collaborated with senior stakeholders or influenced decisions at a high level.
✨Be Ready to Travel
With regular UK travel involved, express your enthusiasm for getting out there and meeting property owners. Mention any relevant experiences you have with travel in previous roles and how it helped you connect with clients or stakeholders.
