We are thrilled to announce that our Managing Director, Jack Cheshire, has been shortlisted as a finalist for the ‘Rising Star’ award in the 2021 Shortyz, a global industry award ran by Short Term Rentalz which celebrates the best and brightest in the holiday rental world.

The ‘Rising Star’ category aims to acknowledge the people and companies who demonstrate enterprise, innovation, drive and provide evidence of making a significant contribution to their business and/or the short-term rental sector, so Jack is honoured to have been shortlisted.

You may not know much about Jack, as he is the man who works behind the scenes making crucial changes, leading our fantastic team and ultimately driving the business forward.

Jack joined the business after an intense 5-year career in corporate finance in London, Dubai and Monaco working specifically in investment banking and private equity funds.

Whilst he thoroughly enjoyed his career in finance, he always had ambitions of one day joining and running the family business, so made the move back to Spain in 2019; taking with him a wealth of knowledge and experience, which ultimately would prove invaluable to the business and its future.

Jacks’ contribution to the business since joining has been inspiring. Alongside a complete rebrand, he has taken us from a manual, labour-intensive business to a progressive, online business, leading us to generate 100% more revenue in the subsequent 12 months.

Following this immediate success, when COVID-19 hit Jack re-evaluated the entire business and identified various gaps in efficiencies, so took the opportunity to implement several other processes, systems and software which ultimately changed the entire business. These included:

  • Switching booking systems allowing for more efficiencies, automations, streamlining, etc.
  • Implementing a maintenance management system to better organise maintenance, inspections and co-ordinate cleans, etc.
  • Using the latest technology to enable seamless guest check-ins, individual property apps, digital guest welcome packs and property guidebooks, etc.

These changes enabled us to automate roles to grow the business without the need for hiring more staff and allowed the existing team to benefit more from their roles, grow within the business and take ownership of the things that they most enjoyed, rather than merely performing repetitive daily tasks. This boost in motivation alone generated a noticeable shift in the team’s approach to work and their output.

Jack is a great leader and motivator for the team, and we are proud to work both with and for him.

This is an amazing award to have been nominated for, and we thank ShortTermRentalz and the amazing panel of judges for acknowledging Jack's efforts and contributions to the business and the wider industry. If you want to show your support, please click here: https://bit.ly/3sgicHw to vote for Jack. Voting closes on the 29th of March so get there quick!