Hayden, who has worked in real estate for 14 years started his career in 2005 with Harcourts at Twiss Keir in Canterbury and was trained under the careful guidance of James Twiss. Early in his career he won the Real Estate Institute of New Zealand (REINZ) novice auctioneer of the year and has continued auctioneering since. In 2007 Hayden was asked to joined another large real estate company and moved to Auckland as their Business Development Manager for Auckland and Northland. Following this he went on to open his own real estate business under that same brand in 2009. In 2012, he opened the second office of his growing business. This was all achieved while undertaking a Graduate Diploma in business studies majoring in real estate and obtaining his Accredited Real Estate Industry New Zealand (AREINZ) status.