“hello2HIRED” Event: Not Caymanians Versus Employers. Instead, A Room Full Of People Trying To Match Up

By Alric Lindsay

About a hundred job seekers registered for the hello2HIRED event at the Grand Cayman Marriott on Monday afternoon, August 24, 2026, an initiative of the Ministry of Caymanian Employment.  The event did something simple and unusually effective: it put employers and Caymanian job seekers in one room, from 3pm to 7pm, and let them talk to each other.

The conversations were candid, and the most encouraging thing about them was where employers placed the responsibility. Again and again, they placed it on themselves.

“We are just like everybody else complaining about the shallow pool,” said Woody Foster, whose group includes Foster’s Food Fair, HomeGas, CarCity, Arch Automotive, Heights and Progressive Distributors. “But what are we doing to make it better? I don’t want to just complain. I want to do something about making the system better.”

The group employs about 1,300 people. Depending on which immigration definition is used, Foster put the Caymanian and RERC share at around 45 per cent measured against full work permits. Turnover runs at roughly 30 per cent, which means the company is recruiting more or less continuously. “So hiring is one issue, and the secondary issue is retention.”

He was straightforward about what makes those roles a harder sell. “Our industry is not a very sexy industry. We’ve got to work weekends. We’re not open 24 hours, but we’re basically working 24 hours. You’ve got chefs that come in at four in the morning and bakers that come in at two in the morning, and our warehouse crew works through weekends because that’s when the boat comes.”

He also repeated a comment the company hears: “Well, you don’t want to be seen to be working at Foster’s. That’s seen to be a step down.” His reply was the line of the afternoon. “We are entry-level, and we’re a stepping off, not a stepping down.”

Asked where responsibility for changing that perception of job attractiveness — the home, the school, the employer — he took it on. “I think it starts with us. We need to believe ourselves that we have something to offer, that we’re not just a bunch of cashiers and shelf packers. We have lots of technical and vocational type jobs — meat cutters, bakers, chefs. We are not doing a good enough job of leaning into that and really embracing that ourselves.”

There are concrete plans behind that. The group has brought in a new HR manager and a new chief operating officer, both tasked with building internship programmes, and Foster wants working relationships with UCCI and John Gray so that recruitment starts while students are still in secondary school rather than after graduation. “They know us. We know them.” He pointed to people who joined at entry level in the HR office and now run HR companies. “We’re just a part of the process.” Two hours in, he had two solid leads and five or six applications.

Letitia D. Hirst, a representative of the restaurant group behind Abacus and Karoo Local said the group had come looking for servers, bartenders, kitchen helpers and cooks, and had already had encouraging conversations. “We’ve had a few people that showed some interest today, which is very good.”

She was clear that inexperience is not the barrier people assume. “One of the biggest challenges is either that they don’t have the experience — which we’re willing to train, we’re willing to train.” The friction comes later, she said, when candidates learn about the hours and the long periods on their feet and weigh those against family commitments.

Rather than hire someone into a role that will not suit them, the group looks for people who genuinely want to work with the public: “We don’t want to go hire someone and they’re unhappy.” Her commitment was unqualified — “we’re willing to train, willing to take on as many Caymanians as we can” — and the group had just hired two young Caymanians, taking its Caymanian and permanent resident share to somewhere around 10 to 15 per cent.

Asked whether the missing skills could be taught in high school, she gave an answer that several other employers echoed in their own words. “To be honest with you, it all boils down to the person, their personality. If you are not a people’s person, no training on earth is going to help you in that area. You just can’t say I want to be a server because that job is available. That has to be a passion.” She was careful not to be heard dismissing education: “Of course school is helpful. I am not saying education is not helpful. But to actually do a job, love it, a passion for it — that has to be instilled.”

At Lobster Pot, manager Brigita Nemet described a market where the opportunity is real but the information has not reached the people who could use it. She has seventeen full-time staff and six part-time, of whom four full-time and six part-time are Caymanian. Front of house fills readily; the kitchen is harder.

Her diagnosis was about earnings being misunderstood. “Maybe previously Caymanians were not interested to work as servers because they thought that they cannot make money. Maybe they are not aware that the hourly rate is not reflecting on how much money they’re going to make.” In a job built on gratuities, she said, “it doesn’t matter it’s minimum wage — you can make actually almost a lawyer’s salary on a minimum wage.” She believes the message is starting to land: “Now I think the word is out.”

Asked what she would change if she were the minister, she offered something the ministry could act on tomorrow: publish the numbers. Make clear what a valet, a bellman or a server can actually earn, and explain the seasonal pattern — by her estimate two to three times more between December and March than in the slow months — so that people entering the industry understand how to plan across a year.

The same seasonal logic came from Kimberly Dangerfield of Clearly Cayman Dive Resorts, which runs the Cayman Brac Beach Resort and the Little Cayman Beach Resort, with the Reef Divers dive operation at each. The group employs around 90 people across the two properties and is about to add a third in Little Cayman. “So we’re excited about that.”

Her recruiting challenge is particular to the Sister Islands. “It’s a case of leaving the comfort zone of Grand Cayman and trying something new. Trying to go from a small island to an even smaller island can be a hard sell.” Her answer is to sell what is actually there — on Cayman Brac, “you have healthcare, you have education, there’s a great airport, there’s a real infrastructure” — and to be explicit about progression. “You may come in in this role today, but we’ve got a lot more opportunities.”

On the earnings misconception, she was direct about how to work the season. “A savvy individual would pursue a position like a server or a hostess or a bartender, particularly in the high season in Cayman, because that is truly when there’s a lot more significant income to be made. You make hay while the sun shines.”

Asked where the work of making these jobs attractive begins — home, school or a government programme — she said none of those alone. “It’s a collaboration. It’s real-life experience and exposure. You come to the properties, then you truly see not just through an associate’s eye, but through the guest’s eye. And who doesn’t love hospitality? When you get to deliver that experience, then you become part of that world, and the opportunities grow from there. There’s a lot of misconception of hospitality, but to me, there’s no more exciting industry to be in.”

Hers was also the one internship programme at the event that already exists rather than being planned. Working with Layman Scott High School on Cayman Brac, and running for years, it puts an intern through a month in each area of a resort across six months — housekeeping, front office, culinary — and offers open water dive certification at the end for those who want it. “So they leave with another skill set. We love that internship programme. It’s been very popular.”

L-R: Brigita Nemet, Nazeer, Kimberly Dangerfield

A representative of Flow, which employs 107 people of whom about 90 are Caymanian plus permanent residents, said the gap she encountered was preparation rather than willingness.

She shared:

Several of them need to have that workshop to help them write their resumes, be able to sell themselves when they come to an interview. We know that everybody isn’t going to come with the experience, but to get their foot in the door, they must be able to at least sell themselves a little bit.

Flow’s response was practical, and worth other employers copying: rather than simply declining candidates who interview poorly, its team spent the day giving feedback on the spot. “We don’t just say, well, you didn’t do a very good presentation. We will pull information out of people to figure out where they want to go and how to better themselves.”

She also challenged an assumption that shapes a great many career choices. “It’s a statement that I hate to make — not everybody can be an accountant or a lawyer.” Training programmes, she noted, are mostly built for office work. “There’s nothing wrong with being a mechanic.” Her illustration was an air-conditioning technician called out in the middle of the night, who might charge $400 for thirty minutes. “So people can make money in those positions. You don’t have to be in a bank. But we have to make those jobs attractive. Stop making them sound as if they’re uneducated people who are doing that.” Change that mindset, she argued, and the rest follows: “you’re going to learn skills, you’re going to be certified, and you can offer a service.”

Jennifer Leach-Tippetts of Massive Rental and Sales offered evidence that the retention problem is solvable. The company has 41 or 42 staff across event and construction rentals and heavy equipment sales, and many have been there ten, twenty and twenty-five years. Recruiting into warehouse and rental agent roles is the harder part — lower on the salary scale, and often outdoors.

Asked how you make a warehouse job attractive, she responded cheerfully. “We have a good reputation. A lot of people, when I say, do you know Massive? Oh yeah, we see the guys in the shirts, we see your trucks.” People want to work there, she said, because the company is known as a good employer. The company interviews twice, the second time with the supervisor for the role, precisely to get the fit right.

Douglas Cameron Jr, a food and beverage supervisor with Gyro Hut group of companies, including Al La Kebab and the Hive, made the case that better matching, rather than more applicants, is where the gains are. “Every sector has a unique employee, whether it’s skill set or personality type. You can’t put a square block into a round hole. Every individual, every person needs a job that suits them. You can’t force them to work in a sector they are interested in.”

He described what hospitality actually asks of someone — “standing on their feet for eight hours in a boiling hot kitchen” and, on the front line, absorbing a difficult customer and carrying on — and drew a conclusion that deserves more attention than it usually gets: “hospitality isn’t necessarily an entry-level position for all personalities.”

He added:

We do have a great training program.  For the last couple that we’ve hired, everything is awesome.  They’re super happy. We’re super happy. And for the first couple of weeks… and then… I think the priorities change.  They stop showing up on time or even showing up at all. And we start to run into some of the background problems why they can’t come to work all the time.

He continued:

In hospitality, if someone doesn’t show up for a shift or of someone is late, the whole team really suffers.  And sometimes you can’t fill the spot.  You know, if a cook doesn’t show up, you can’t cook any meals.  Luckily, we’re big enough to have multiple cooks. So, someone just has to end up working a double shift or not getting a day off that week.

His advice to the ministry was to make a more aggressive push for work placement programs where students can do internships at companies to get a feel for how it is to work at those companies. “That is a great program,” he said. The ministry could also look hard at where education and training effort is being directed, so that people are pointed towards work that fits them.

A representative of Workforce Opportunities and Residency Cayman was at the event explaining the mechanics of the WORC jobs portal — the part of the process job seekers most often say they do not understand. Once a Caymanian is registered, she said, they can review the opportunities posted and apply through the system. The employer sets what is required: “they might say, I’m good with just a cover letter, or I want a cover letter and a resume, or I just want the resume.” The application is meant to land in the employer’s inbox with a link through to the job seeker’s account.

What happens next is the part worth knowing. “Once they make a decision whether they’re going to interview or not, they can place a comment in the system,” she said — and that comment is visible to the job seeker. It can also be seen by the boards where a work permit is involved, and by the employment services unit where the applicant is one of their clients. Where an employer posts an advertisement and receives Caymanian applicants, “we encourage them to still put a comment on the system,” so that the outcome is recorded rather than the trail simply going cold.

The portal is open to Caymanians and permanent residents. Employment services support Caymanians who elect to receive them, and that is a smaller and more hands-on operation: of the thousands using the portal, “let’s say a few hundred come to us.” Each is interviewed at what she called the intake stage, to establish what they are qualified for and what they want, and an action plan is agreed. Her team reviews jobs posted in the previous 24 hours and matches selectively rather than in bulk. “I’m not matching you for a boat deck hand if it’s admin that you’re looking for.”

The event also brought the other side of the table into the room, and it is worth remembering who that is. One woman in her early fifties, a Caymanian, had come because her employer had told her the company restructured and that her post as an office assistant was made redundant. She was not despondent about it. She had come to hello2HIRED hopeful of finding something, and the format — employers in front of her, able to talk rather than acknowledge an application — is exactly what someone in her position needs.

Her situation is a useful corrective to the way this debate is usually framed. She is Caymanian, she is experienced, she is willing, and she is looking for work through no fault of her own. Every employer at the event said they were short of people. The task is connecting the two, and that is precisely what the afternoon was designed to do.

Another job seeker offered a different vantage point. A bartender of fifteen years who first came to Cayman in 1998 as an 18-year-old, married to a Caymanian and no longer holds a work permit. He said the change in his immigration status had given him a sympathy for Caymanians he had not had before.

“I finally understand the reason when people…when Caymanians used to say, oh, it’s so hard to get a job,” he said. “I finally understand that part of it, because I’m not on a work permit anymore.” In his experience, a worker on a permit is in a weaker position to negotiate: “when you’re on a work permit, people tend to hold that little axe over your head…it is easier to control you when you’re on a work permit.” When you’re not on a work permit, he said, it is more difficult because an employer knows “that you will stand up for yourself.”

It is one person’s account rather than a finding, and he was describing the same market the employers had been describing, from the opposite side of it. Taken together with what the companies said about pay scales, hours and lean staffing models, the two views are not in conflict — they are the same picture from two chairs.

What made the afternoon useful was that nobody left it at diagnosis. Publish what hospitality roles actually pay across a season. Run resume and interview workshops before the next event. Give candidates feedback rather than a silence. Build internships and start the conversation with students in secondary school. Interview for fit rather than for a CV.

Premier and Minister for Financial Services and Commerce, Hon. André M. Ebanks, MP, who came through the room during the afternoon, made the case for doing it again.

He shared:

What I walked in and witnessed was Caymanian job seekers getting direct access to employers, and employers being able to make judgments as to whether or not they are worth hiring, worth following up. This cuts through all the application process, which is manual or stuck into AI to sift through employees. This is direct face-to-face contact by Caymanian job seekers with employers.

He was unequivocal about what he had seen. “hello2HIRED has enormous, enormous potential, and I hope it continues more frequently. I’ve already seen maximum potential for this to work today.” If the success rate holds, he said, the ministry should run it “more frequently, maybe even quarterly, to continue to get Caymanians into good jobs and take this country from strength to strength.”

Premier Hon. André M. Ebanks (left) seen here with attendees

The Minister for Caymanian Employment, Hon. Michael Myles, whose ministry ran the event, described it as one piece of a wider effort to join up parts of government that have not spoken to each other. “Government was very siloed and very separate. What our government is trying to do is bring those pieces back together, so we’re not duplicating people’s services.”

Part of that joining up is educational. The minister backs the plan of Hon. Rolston Anglin, the Minister of Education, to make CIFEC, the Cayman Islands Further Education Centre, the island’s technical and vocational education and training hub, with the various TVET programmes brought under it — a CIFEC student wanting to train in a salon would be referred on to the Cayman Career Academy, or into dual enrolment at UCCI, while remaining within one system. “I believe in that vision that he has. It can’t happen soon enough.” He noted that the same goal was set when he worked in the ministry between 2009 and 2013.

He also wants somewhere for internships to live. “We still do not have a proper website to house all internships,” he said. “It is too frustrating for an individual to look on a hundred different sites to try to find an internship, when really we should just have a list.”

He gave a concrete example of what that has already produced. “For the last decade, employment and labour had no clue that there were 1,500-plus kids overseas, because none of that information was shared,” he said — the two functions sat in separate ministries. “Well, we’ve changed that. I now know who those students are, and I’ve given 1,500 names to recruitment centres and hiring managers. So those students are now being seen.” The ministry has also signed an agreement with Cayman Connection, which has some 2,000 students registered.  He also mentioned the relationship with Cayman Finance, which is helping to place Caymanian graduates.

He added:

We need to build a better database. The jobs portal is only a small piece of that. It’s not being utilized.  Why? For whatever reason, our people think that the moment that a job goes on a portal, [it means that it is for a] work permit. So, they don’t bother look at those jobs. But we put those jobs in the papers, and now it’s stimulated our people to apply for those jobs.

He emphasized that, although efforts are being made to make the WORC portal increasingly user-friendly, publication in newspapers has proven to be more “impactful.”

Explaining this, he said:

Our employment services unit barely places 10 people a month. And just July alone, [after] the law came into effect, we placed 25 people. Why? A majority of those people saw those jobs in a printed newspaper. I’m hoping that August will be the exact same way. 

That’s why we are having things like this. 

We also have to connect people. You would have heard, if you’ve interviewed a number of these people, the frustration is that I’ve applied to a job, I don’t hear anything back.  That’s why these things are necessary. I need to bring people together where they can sit, have a conversation.

Minister Myles (right) discussing issues with an attendee

The minister has also put money behind the two hurdles that come up most often. Where a single mother needs childcare, or someone from the eastern districts cannot afford the bus fare, the ministry will assist, rather than referring them back to the welfare office. “We have a budget that if you need childcare and you have a job opportunity, then we will pay childcare for you until you get settled in the job.”

He is realistic about the limits — “I’m not under any illusion that we’re going to fill every job in the Cayman Islands” — and about the scale of the problem, which he puts at “probably about a thousand” unemployed, with underemployment a separate and larger question. But on the scale of the place, he is optimistic. “We’re in the Cayman Islands, where we have a very small, tight-knit [community], and we can fix this problem. We really can.”