A senior manager at DMZ, which is delivering the Cayman Islands’ first Launch Labs Incubator programme with Enterprise Cayman, described a cohort with exceptional knowledge and business experience.
Alexandra Ali-Dib, the Toronto-based startup incubator’s senior manager for global programmes, said she left the opening week in Grand Cayman feeling energised.
The early September sessions brought together founders from the programme’s 18 ventures, spanning finance and investment, business software, health and wellbeing, and local culture and heritage.
“The amount of knowledge in the room, the quality of business was exceptionally high compared to maybe what I have experienced in other jurisdictions around the world,” Ali-Dib told Cayman Independent.
“They’re all very accomplished people that have done incredible things in their careers already, and they’re sort of ready to do their own thing.”
The 14-week programme runs from 1 September to 4 December in partnership with Enterprise Cayman, the non-profit initiative created by Cayman Enterprise City (CEC).
DMZ, the tech incubator at Toronto Metropolitan University, has worked on startup programmes around the world, including in Japan, Egypt, Qatar, Turks and Caicos and Jamaica, Ali-Dib said.
A community forming
Ali-Dib said most of the founders had never met before the programme began, even in a business community far smaller than in Toronto or San Francisco.
Once they met in person, she said, they quickly began pulling one another into their existing networks, from a Friday-morning AI working session to Sunday sailing.
The cohort’s WhatsApp group exchanges around 50 messages a day, by her estimate.
“They really are helping to raise each other up,” she said.
Ali-Dib said the wider business community had also turned out.
At an informal evening where the projects were introduced, people who had already had successful exits of their own offered feedback and connections.
“What I saw when I was down there was pretty serious community support,” she said.
Inside the programme
Participants take part in weekly virtual workshops led by DMZ. Meetings and optional in-person events are held on Wednesday evenings at CEC’s Signal House.
The programme’s stated objectives include accelerating launch and commercialisation and strengthening Cayman’s startup ecosystem and global connectivity.
One of the first workshops asked founders to pin down their ideal customer profile, value proposition and business model, Ali-Dib said. The curriculum is divided into four blocks:
- Strategic foundations: Market research and validating the problem and solution
- Go-to-market and sales: Customer acquisition and building repeatable sales processes
- Financial and growth strategy: Financial planning, pricing and revenue models
- Execution and investor readiness: Preparing founders to pitch
Ali-Dib said DMZ is combining the group sessions with one-to-one support, because the ventures are at very different stages, and each team is paired with a dedicated mentor.
“We can’t do a one size fits all,” she said.
Participants also receive membership of the Cayman Islands Venture Founders Society and a year’s membership of Launch Labs Studios, a co-working space at CEC.
Looking beyond Cayman
One challenge for Cayman-based businesses, Ali-Dib said, is that a small local population means companies “have to look globally to build their customer base”.
That means founders must keep re-evaluating their ideal customer profile outside Cayman as they grow, she said.
Each time, they have to test whether what worked in Cayman will work in the Bahamas, Miami, Toronto or the UK.
That global focus had been built into the programme from the first week, she said. With DMZ’s offices around the world, the incubator could help founders reach new markets beyond Canada and the United States.
She also said she hoped DMZ will act as a bridge between the Cayman and Canadian startup communities.
Canada, she noted, is looking at trade diversification. “The United States is no longer a really good option for us,” she said.
That is one reason she sees programmes like this as important, and argued that Canada and Cayman could lean on each other for innovation.
“Technology that’s built down there can be tested up here,” she said. “I know traditionally a lot of companies from Cayman do look to Miami just because of proximity, but there’s no reason that it couldn’t be Toronto.”
What comes next
The founders will have peer feedback sessions and a pitch retreat in Grand Cayman in early December with a final pitch event on 3 December.
There, participants will present to an audience that includes members of the Cayman Islands Investment Angel Society.
Applications for the 2027 cohort have not yet opened, but Enterprise Cayman is accepting registrations of interest.
