Jill Caisey used to curl up with her husband Chris in their seacoast home in New Hampshire and dream about a life in Hawaii. Their weekends were spent skiing in nearby Vermont, but they’d wrap them up on Sunday evenings “religiously binge-watching” episodes of HGTV’s Hawaii Life. They imagined trading in their ski weekends and those frigid East Coast winters for a life spent surfing, paddle boarding, running and biking.
A Proven Sales Track Record
With a thriving career in Biotech, Jill was a driven sales professional with a proven track record in Biotech and Medical sales. They had visited O‘ahu, Maui and the Big Island on incentive trips – vacations earned by the most successful sales professionals on her company’s national team. In 2011, Jill’s employer suggested a potential need for a full-time salesperson in the islands. With more than 30 sales awards to her credit, she was being considered for the role. Jill and Chris began to imagine realizing their dream of a Hawaii life.
HGTV’s Hawaii Life Appearance
Several mergers and acquisitions later, her company’s job role in Hawaii hadn’t materialized. One evening, 4 or 5 episodes into a binge session, Chris declared, “We should be on that show!” Then he set the wheels in motion and reached out to the show’s production company. They set up a simple Skype interview. “We were already planning a 3-week trip to Kauai, which was the only Hawaiian Island we hadn’t been to yet. Our vacation quickly turned into a home-buying mission,” notes Jill, now in her first year as a professional realtor with Hawaii Life.
A Cross-Country Move to Kauai
Chris and Jill appeared on HGTV’s program in 2013, on a house-hunting mission that led her straight to Hawaii Life’s doorstep. The episode was called “New Hampshire to Kauai”, and it appeared in Season 2 of the HGTV’s popular program. “We took a giant leap of faith and moved across the ocean to recreate our life on Kauai. I remember being filmed for the show and thinking that one day I would be an agent for Hawaii Life,” said Jill. She and her husband purchased a home in Kapaa, on the East Side of Kauai, and they moved to the islands in 2015. A little bored with her self-imposed early retirement, Jill sought out Hawaii Life as a means of flexing her sales muscles while also keeping a flexible schedule to enjoy her new lifestyle.
A New Career
As for the career change, Jill is enthusiastic about the changes she’s made. “I love the culture at this company and believe it to be one of the truly genius marketing engines of the entire real estate industry. This company feels like home for me and thankfully I have used my work ethic along with the tools provided here to gain momentum early on.” She’s enjoyed some early successes, and her new role as a realtor allows her the flexibility to travel and to work remotely when she needs to.
A Kauai Lifestyle
Jill’s been enjoying her Hawaii lifestyle on Kauai for the past three years with her husband Chris and daughter Ella. They enjoy surfing, hiking and biking. “It feels like a very healthy lifestyle living here. We are no longer dealing with winter, where you’re sedentary and stuck in the house, and you make every excuse not to go outside,” said Jill. While they used to surf occasionally in wetsuits in New England, they couldn’t do it every day. Now her husband Chris has worked out his schedule so he’s able to go surfing every day. Jill and her family still get the chance to play in the snow now and then. They recently returned from a 10-day ski trip to Jackson Hole.
Casting Call
Get in touch with Jill:
Check out a few of Jill’s blogs.
Learn more about available properties on Jill’s website.
For additional information about Hawaii real estate, please don’t hesitate to contact Jill via email.
Jill Caisey, REALTOR, RS-79794
808-634-8062

Jill and family hiking on the North Shore of Kauai.
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