LEADER – JACKIE DOAK, DIRECTOR OF THE DART GROUP: "IT'S NOT JUST ABOUT BUILDING HOTELS, BUT ABOUT CREATING OPPORTUNITIES THAT SPAN GENERATIONS" (Cayman Islands)
For more than twenty years, Jackie Doak has been part of a company that has been innovating hospitality in the Cayman Islands by combining excellence, sustainability and local roots within the Dart group.Category: North America & West Indies / Carribean islands - Cayman Islands - Hotel projects Career - Interviews
Interview made by Vanessa Guerrier-Buisine on 2025-09-15
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 Jackie Doak is the director of the Dart Group
This inspiring leader began her career as a specialized commercial litigation lawyer before succumbing to the charms of her native island. The development of Camana Bay, a Caymanian town designed as a complete ecosystem, marked a major turning point in her career. Enticed by this project, she joined Dart Realty in August 2003 as Vice President of Sales and Leasing before being promoted to COO. Thirteen years after her return to the Cayman Islands she was appointed President of Dart, a strategic role she held until 2022, before focusing on Director duties for the Dart group as a whole.
Since then, she has overseen Dart Family Office, Dart Enterprises and Dart Interests in the United States. At the same time, she has been actively involved in Dart's hotel expansion, with properties that have become iconic, such as the Kimpton Seafire Resort + Spa, The Ritz-Carlton Grand Cayman and the Four Seasons Anguilla, all awarded five stars by the Forbes Travel Guide.
In an interview with Journal des Palaces, she discusses Dart’unique hotel development model, the group's eco-friendly ambitions, and the key role played by local training and promoting the region. One conviction guides her career: ‘It's not just about building hotels, but about creating opportunities that span generations.’
Could you outline your career path? This question is used to write the introduction, so bullet points are fine.
My career path has been an exceptional journey, one shaped by a desire to lead and make a meaningful impact. I began my career as a lawyer, practicing commercial litigation in Florida. While I valued the discipline and analytical rigor of the legal profession, I felt a strong pull back to the Caribbean and the Cayman Islands, where I grew up. Returning home allowed me to reconnect with my roots and contribute to our family business.
In 2003, the Dart group announced that they were developing a new urbanism inspired town, Camana Bay, and I was intrigued by the vision of the company. I met with the leadership team and joined Dart as Vice President of Sales and Leasing, marking the beginning of a transformative chapter. Over the past twenty years, I’ve had the privilege of growing with the company, taking on diverse roles and contributing to projects that have helped shape the real estate and hospitality landscape in the Cayman Islands and beyond.
Each step of my journey has been guided by a commitment to excellence, a passion for placemaking, and a belief in the power of relationships and collaboration. It’s been a remarkable experience—one that continues to evolve and inspire me.
How would you define the Dart's DNA and the values that guide you?
The Dart group of companies has an 88-year history rooted in a manufacturing business in Michigan that grew into Dart Container Corporation and whose products include the iconic red Solo® Cup. Ken Dart moved to the Cayman Islands in 1994, starting with a small investment office.
We are guided by values, eight guiding principles, that our founder Ken Dart has imbued throughout the company – Teamwork and Respect, Reason and Logic, Honesty and Integrity, Dedication and Industriousness, Meritocracy, Personal Accountability, Innovation, and Profitability.
Collectively, these values create a culture where excellence is expected and empowered. They foster an environment where innovation and ideas are valued, individuals are held to high standards, and collaboration drives progress. By staying true to these principles, Dart is more than a developer. Through master planning and placemaking we create exceptional places, experiences, and opportunities that enrich lives now and for future generations.
Today Dart’s real estate interests encompass hospitality, residential, commercial office, retail, entertainment, energy, education, infrastructure, and lands.
All Dart businesses are unified by long-term perspective and creation of enduring value. The Dart group does not look at financial returns just by quarters or years, but thinks in terms of decades. As a Director at Dart, this generational outlook and positive impact on the communities where we invest and develop is the source of my inspiration every day.
How much has Dart invested in the hotel industry since the group entered this market less than 10 years ago?
Our hospitality journey started with the Dart-designed and developed Kimpton Seafire Resort + Spa which opened in November 2016 and was soon followed by the Residences at Seafire. Beginning with Seafire, Dart has made a multi-billion-dollar investment in more than 10 hospitality properties in the Cayman Islands, Anguilla, and the United States.
Today our luxury resort portfolio includes Kimpton Seafire Resort + Spa, Grand Cayman, The Ritz-Carlton, Grand Cayman, Four Seasons Resort and Residences Anguilla, Zemi Beach House, Anguilla, Conrad Orlando at Evermore and Evermore Orlando Resort.
With our long-term perspective and value creation, Dart not only invests in, but continues to reinvest in our hospitality assets to ensure they are innovative and exceed our guests’ expectations
An example of this is The Ritz-Carlton, Grand Cayman which Dart purchased in 2017. After a record-shattering performance in 2019 and the Cayman Islands’ extended border closure during the pandemic, Dart elected to close the hotel and invest more than $55 million in a comprehensive enhancement. This meant pulling years of capital expenditure forward, with renovations that extended far beyond the standard 7-year refresh. The Ritz-Carlton Grand Cayman will celebrate its 20th anniversary in January as the region’s only Forbes 15-star resort.
Dart’s ongoing investment in our hospitality portfolio has resulted in three resorts – The Ritz-Carlton, Grand Cayman, Kimpton Seafire Resort + Spa and Four Seasons Resort and Residences Anguilla – that have been recognized by Forbes Travel Guide as Five-Star Award Winners. In 2025, Dart was recognized as Forbes Travel Guide’s first Ownership Group of the Year.
Do you have any significant short- or medium-term investment projects in the hotel industry in the Cayman Islands and internationally?
In response to the growing demand for the Cayman Islands’ distinctive blend of unpretentious luxury set within a safe and prosperous environment, we are currently in the development planning phase for our next luxury resort on Seven Mile Beach in Grand Cayman. This new property will embody Dart’s commitment to innovation, excellence, and placemaking—creating not just a destination, but an experience that elevates the Cayman Islands’ global luxury hospitality offering.
Dart’s pursuit of the extraordinary extends beyond Cayman into Anguilla, Dart’s second market that is a British Overseas Territory. Following initial investments into landscape, sustainability initiatives, a new café and an enhanced canteen for employees, our design, and development teams are working on transformative reimagining of all guest rooms and villas at the Four Seasons and conceiving a new destination spa to be created at the property.
Dart acquired Zemi Beach House in Anguilla in December 2024. We’re considering what enhancements we can make to that resort which is a favourite among both celebrities and families who return year after year.
We’re also considering the best opportunity for the next phase of development at Evermore Orlando Resort. Evermore is a once-in-a-generation project. On 1,100 acres adjacent to Walt Disney World, Evermore represents an entirely new hospitality concept in the U.S.’s second-largest accommodations market. With more than 2,000 rooms in large houses, modern residences and classic villas, Evermore is designed for families and groups of friends to gather in professionally managed luxury vacation homes.Evermore is anchored by the modern luxury of the 433-room Conrad Orlando and surrounded by 36 holes of golf on Jack-Nicklaus signature courses. But the showstopper is the eight-acre Evermore Bay. Enveloped by beaches with a rope swing, waterslide and cabanas, Evermore is an island-style retreat in central Florida.
What criteria guide your choice of hotel operators (Marriott with Ritz-Carlton, Hilton, Four Seasons, and IHG with Kimpton and Indigo, etc.)? How does Dart's relationship with its international hotel partners work in terms of recruitment, innovation, guest experience, and operations?
Dart is agnostic as it relates to brands, management models, development approach and acquisition strategy. The selection of a hotel operator for each property is customized for the unique site, property, and experience – there is no one playbook. Dart is an active owner, collaborating closely with each management company on long-term opportunities to attract new customers and earn returning guests’ loyalty.
This is demonstrated throughout our luxury portfolio that includes properties we have developed (Kimpton Seafire Resort + Spa, Conrad at Evermore and Evermore Orlando Resort) and venerable properties we have acquired and enhanced (The Ritz-Carlton, Grand Cayman and the Four Seasons Resort and Residences Anguilla). Our three Forbes five-star resorts are managed by three different brands.
How does Dart approach sustainability, eco-responsibility, and environmental integration in its hotel projects? Can you tell us about your laundry business in particular?
As with all of Dart’s developments, our hospitality investments seek balance between economic growth and environmental and social responsibility. Dart’s first hotel, Kimpton Seafire, was the first resort in the Caribbean to be certified LEED® Silver by the U.S. Green Building Council.
Dart has invested in innovative public private partnerships to create resilient infrastructure. With market-leading investments in renewable energy, Dart is currently responsible for 11% of the Cayman Islands’ solar power production.
As Dart’s hospitality portfolio grew, our engineers developed the concept for a central laundry facility to pursue operational and energy efficiency. Cayman Linen Services allows Dart to process laundry for all its Cayman hotels in a single place, saving more than 17.8 million gallons of water per year. The relocation of the hotels’ laundry facilities also freed up valuable back of house space that was repurposed for our operational teams’ most pressing needs.
The most visible indicator of Dart’s sustainable approach is landscape. At each Dart property, the grounds are just as important as the buildings in creating an immersive experience. More than a decade before Camana Bay opened, Dart established the largest potted plant nursery in the Caribbean. Dart’s hotels are designed with native plants and trees that provide habitat for birds and butterflies while cooling the landscape. Inspired coastal green spaces add to the guest experience with pockets of privacy and natural beauty.
Kimpton Seafire exemplifies the leading role of landscape in the Dart DNA. The resort is set back from the beach ridge’s natural vegetation line. Seagrape trees that have protected the shoreline for generations provide guests with pockets of shade and picturesque natural seating on the sand. Cayman limestone boulders shape the resort’s cascading landscape along with thousands of plants, shrubs and trees, most of which were cultivated in the Dart Nursery.
Three of your hotels and one of your restaurants have been awarded five stars by Forbes Travel Guide. What does this distinction mean to you? How are you working to upgrade your properties and complete service excellence?
We are extraordinarily proud of the star designations that have been earned by the talented hospitality professionals of our three Forbes five-star hotels. The Ritz-Carlton, Grand Cayman has 15 stars for the hotel, spa, and Blue by Eric Ripert, which is also the top-rated restaurant in the Caribbean according to La Liste and Chef Ripert’s only other restaurant beyond Le Bernardin in New York. Kimpton Seafire has 10 stars for the resort and spa. Only a few months after being awarded five stars each, the spas at both The Ritz-Carlton and Kimpton Seafire are undergoing enhancements to ensure we are exceeding the expectations of our discerning guests.
Service excellence is an ongoing pursuit. Our partner brands share Dart’s belief in continuous improvement through learning, development, experience, and innovation. As an owner Dart supports this through multiple initiatives – from seeking training from external authorities in travel and luxury to having chefs from properties outside of Cayman experience Cayman Cookout at The Ritz-Carlton to exchanges between food and beverages teams in Anguilla and Cayman.
The Dart training program for young Caymanians seems innovative. What are the objectives and initial results? How many young people have already been trained? What is the employment rate for graduates in your properties?
The largest industry in the Cayman Islands isn’t tourism; it’s financial services. With Cayman’s diverse economy, which is growing through technology, reinsurance and family offices, resorts must compete to interest young Caymanians in the rich opportunities a career in hospitality can offer. Dart chose to partner with Lynn University in Boca Raton, Florida to create a custom apprenticeship. The Dart Hospitality Training Programme provide students with classroom instruction and paid work opportunities to identify and develop their talents in delivering anticipatory service. With only a few exceptions who have accepted positions in other industries, the programme graduates have gone on to full-time employment within the Dart portfolio of properties.
The Dart Hospitality Training Programme is the latest in a long history of initiatives to help with youth development in the communities Dart serves. Dart Scholar has provided high school and university scholarships, work experience and educational enrichment for more than 40 Caymanian students. The company has a legacy of supporting STEM education, most recently with Minds Inspired, a programme centered on robotics, math challenges and sustainable development competitions.
What role does Dart play in developing local talent and the hotel industry on the archipelago? What percentage of your staff are local employees?
Caymanians and permanent residents are an integral part of the 2,300-person workforce at Dart-owned hospitality properties. Dart is the Cayman Islands’ largest private employer. Our team members can move within the Dart group or properties and companies to experience other markets, learn from different brands and leaders and grow their own experience and perspective.
You are particularly committed to developing a real community in the places where your teams are based. Could you give some examples of structural initiatives that are underway or planned?
While Dart is becoming known for its hospitality investments, our flagship development is the walkable, mixed-use and master planned community of Camana Bay. Unlike many communities which begin with residential development, Camana Bay opened with Cayman International School in 2006 with the Town Centre following a year later.
The town continues to evolve, adding offices, shops, restaurants, apartments, town homes, educational facilities, medical services, a hospital and recreational spaces. Camana Bay’s colourful buildings, open green spaces, landscaped walkways, tree-filled courtyards and waterfront fountains have become a nexus for Cayman life. Camana Bay is a global business centre, a hub for community gatherings and one of the top attractions for visitors to Cayman. Camana Bay is a place to live, work, play, shop dine and learn – a community with the best of the Caribbean for your own best life.
Finally, what advice would you give to young professionals wishing to join the industry?
At Dart we’re big believers in encouraging employees to develop their superpowers – their unique skills and talents that help them excel in work that motivates and fulfils them. Nowhere is this more important than hospitality – where the ability to create exceptional memories for guests, anticipate what they need and help them create connections to the place and people they are with – is at the centre of all success.
We and our brand partners can provide training, but it’s their innate spirit - the unique spark inside each employee - that ignites experiences that earn five-star designations. Dart offers significant opportunities for growth across the organization - as demonstrated by my own journey. That’s what I enjoy and celebrate as we look towards the next decades of growth.
 The Ritz-Carlton, Grand Cayman alone has been awarded 15 Forbes Travel Guide stars
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