Lindsay Baxter had 15 years at the top of one of the world’s largest events companies. She could have gone anywhere. She came to Jamaica, posted on Threads, and accidentally started a movement.
Key Takeaways
- Baxter Spent Nearly Two Decades in Global B2B Events and Media. She Chose Jamaica Over Every Other City the World Had to Offer.
- The Boardroom JA Is Application-Only, Personally Reviewed, and Deliberately Curated. That Is the Model, Not the Limitation.
- The Skill Swap Feature Is the Most Innovative Thing The Boardroom JA Is Building and Nobody Is Talking About It Yet
- The Boardroom JA Is Already Planning Regional Expansion Across the Caribbean
- Baxter Also Runs a B2B Events and Media Consultancy. Her Ask of Jamaica’s Government Is Practical and Specific.
- Lindsay Baxter spent nearly two decades at the top of the global B2B events and media industry, including seven years at Informa, one of the world’s largest events companies, before choosing Jamaica as the place to rebuild.
- She launched The Boardroom JA after a single Threads post asking if any other women wanted to co-work and received an overwhelming response about the specific struggles of female entrepreneurship in the region.
- The Boardroom JA is application-only, personally reviewed, has grown to over 100 members in two months, and is building toward regional Caribbean expansion with a skill swap feature and dedicated app nearly ready to launch.
She posted on Threads asking if any other women in Jamaica wanted to work from a cafe together.
She was sitting alone in her Kingston apartment, laptop open, tired of the isolation that comes with building something new in a city you chose but do not yet fully know. She thought maybe five or ten women would respond.
What came back were long DMs. Pages of them. Women writing about the loneliness of entrepreneurship, about being overlooked for promotions, about business meetings that turned out not to be business meetings, about the specific and sometimes unnamed weight of building a company as a woman in the Caribbean.
“I’ve always championed women in business. When I got that response I felt like I have to do this. Like I’ve been chosen.”
Two months later, The Boardroom JA has over 100 members, an app nearly ready to launch, and a regional expansion in planning. Lindsay Baxter did not move to Jamaica to build a women’s business network. But Jamaica had other ideas.
Baxter Spent Nearly Two Decades in Global B2B Events and Media. She Chose Jamaica Over Every Other City the World Had to Offer.
She spent nearly two decades in the global B2B events and media industry, including seven years at Informa, one of the world’s largest events companies, where she served as Business Development Director and then Product Director. Before that she spent three years at Climate Action, an organization working in partnership with the UN Environment Programme to build business and government collaboration around sustainable development where she built commercial partnerships alongside the annual climate conferences. She led government bids for Singapore and Hong Kong. She had a team beneath her, results behind her, and rooms full of heads of state who understood immediately why she was there.
Then she was offered redundancy.
“I chose violence. If God put something in front of you, sometimes you just follow his path.”
She took the option, spent a few months traveling, and then arrived at the question every person who has built their entire identity inside one institution eventually faces: now what?
A friend suggested a fitness and wellness retreat event for tourists. She had the events background and the passion for travel. She tried Greece first. It moved too slowly, winter was coming, and she pivoted to Jamaica a country she had visited as a tourist, knew through years of living in Brixton, and could get government endorsement from the Ministry of Health and Visit Jamaica. The event, Gains and Planes, ran. It was a B2C learning curve that introduced her to the right people, kept her in Jamaica, and eventually led to everything else.
“If it wasn’t for that, I wouldn’t have met so many amazing people. And if I didn’t meet those people, I wouldn’t still be here.”
The Boardroom JA Is Application-Only, Personally Reviewed, and Deliberately Curated. That Is the Model, Not the Limitation.
Every application to The Boardroom JA is reviewed by Lindsay personally. The most common reason for rejection is simple: relevance. It is a women in business network. That is the criteria. A small number of men have attempted to join the WhatsApp group directly. They have been removed.
The membership is deliberately diverse within that one criteria. Corporate employees on a career ladder who have no plans to leave their jobs sit alongside founders selling physical products — jams, confectionery, immunity shots, juices. Lawyers. AI and tech service providers. Digital businesses. The range is intentional because the value of the network is not similarity but complementarity.
“I knew there was people sitting in their apartments or sitting in a cafe on their own working day in, day out. And it’s lonely. You certainly don’t move halfway across the world to sit in your apartment on your own.”
She set a mental threshold of 100 members as the point at which the group needed to move from one open community to structured silos. She is now building those silos segments within the network organized by industry, stage, and need so that every member is getting specific value rather than general noise.
The application-only structure is not gatekeeping for its own sake. It is a trust infrastructure. In a market where Lindsay quickly learned that doing business in Jamaica requires more face-to-face relationship building than she was accustomed to in London, building a curated network where members know every other member was vetted is a commercial decision as much as a community one.
The Skill Swap Feature Is the Most Innovative Thing The Boardroom JA Is Building and Nobody Is Talking About It Yet
Inside The Boardroom JA app — technically complete, awaiting final back-end work before launch is a feature Lindsay calls the skill swap.
The logic is straightforward and the problem it solves is real. Caribbean entrepreneurs consistently have more ideas than cash. A lawyer who now runs a podcast business needs marketing. A marketer selling handmade products needs legal advice. Both have the skill the other needs. Neither has the budget to pay for it.
“Everyone has a skill to offer and they might have time but no cash. So why don’t we help each other?”
The skill swap creates a structured barter system inside the network. Members post what they need and what they can offer. Terms are negotiated between members directly. The network facilitates the connection and holds the trust infrastructure that makes the transaction feel safe.
This matters more in the Caribbean context than it would in London or New York. Lindsay arrived in Jamaica understanding that the formal professional services infrastructure she was accustomed to — the email that closes a deal, the phone call with a senior title behind your name that generates a response — does not translate directly. Trust is built in person, over time, through evidence of intent and capability. The skill swap builds that trust inside the network before money is ever involved.
The Boardroom JA Is Already Planning Regional Expansion Across the Caribbean
The Boardroom JA started in Jamaica. It will not stay there.
Lindsay sees the network as a regional infrastructure for women in business across the Caribbean islands that are currently operating in similar isolation to the Kingston apartment she was sitting in when she made the original Threads post. The struggles that filled her DMs are not uniquely Jamaican. They are Caribbean.
“The specific struggles that come with female entrepreneurship they do exist in a different way to what men face.”
She talks about the studies showing men apply for jobs when they meet three out of ten listed qualifications and women do not apply when they meet nine out of ten. She talks about potential being extended to men as a courtesy that women have to earn through proven completion. She talks about the specific vulnerability of female founders operating outside the safety of a large regulated company, where the absence of institutional backing changes how some people behave in rooms.
The Boardroom JA is a response to all of that. Not through protest or positioning but through infrastructure. A vetted network. A skill swap. An app. A community that travels across the Caribbean because the problems it is solving travel across the Caribbean too.
Jamaica is the starting point. Two to three more Caribbean countries are in the plan.
Baxter Also Runs a B2B Events and Media Consultancy. Her Ask of Jamaica’s Government Is Practical and Specific.
Alongside the Boardroom JA, Lindsay runs Baxter Advisory, a consultancy working with B2B events and media companies internationally. Her consulting clients are currently all outside the Caribbean the B2B events and professional services market in the region does not yet have the scale of the London market she built her career in, and she has chosen to go deep in her niche rather than broad in a new one.
She is direct about what held her back in the early period of building as a solo operator.
“Wasting time and it’s not until you have the confidence to start moving that you go, what a waste of time that was. You’re updating the website and tweaking a word here or there and changing the PDF. That held me back.”
Her ask of the Jamaican government is specific. Make it easier for skilled migrants and returning diaspora to settle, set up businesses, and access fair certified services. Remove the friction. Create a clear pathway.
“You really do have to have a love for the country to persevere. And I think if there was any of the agencies that could come together to enable that better, there would be a lot more diaspora coming.”
She would still choose Jamaica. She says so plainly when asked. She would do a few things differently. But the answer is yes.
And somewhere in Kingston, Port of Spain, Santo Domingo, Georgetown right now, a woman is working alone in her apartment wondering if anyone else is doing the same thing. Lindsay Baxter is building the answer.
The Boardroom JA: Instagram @theboardroomja
Website: https://theboardroomja.com/
Baxter Advisory: baxteradvisory.co.uk | LinkedIn: lindsaybaxter | Email: lindsay@baxteradvisory.co.uk
You can watch/listen the full conversation with Lindsay on the Foundpreneur podcast.
Foundpreneur covers the Caribbean founder economy. Subscribe to The Foundpreneur Weekly at foundpreneur.co
Stephen Stanberry
