Group Lead / AI Transformation Director

The Opportunity

Dawgen Global is building a Forward-Deployed AI Transformation Group — a small, multidisciplinary team that works inside client operations to find where AI creates value, build it under proper controls and prove the result in numbers. We are looking for the founding leader of that Group.

This is not a conventional advisory role. You will work with boards and executives across the Caribbean, lead controlled implementation and be accountable for whether the investment pays off — while building the Group itself.

What You Will Do

Lead client transformation

• Lead engagements from diagnosis through implementation, scale-up or transition to a managed service.
• Work with executive teams to find business problems where AI can make a measurable difference, and prioritize use cases by value, feasibility, risk and time to impact.
• Lead 30-day sprints and multi-week programmes, client steering meetings and executive presentations, and make — and defend — the evidence-based decision to scale, redesign, stop or transition each initiative.

Prove the value

• Build business cases on measured baselines and hold every engagement to benefits tracking.
• Oversee process and operating-model redesign so that the way work is done actually changes.
• Ensure governance, risk classification and controls are built in from the first day of every deployment.

Build the Group

• Lead engineers, process, governance, cyber and change specialists across two- to four-person client pods.
• Own engagement economics, quality and delivery standards.
• Build reusable methods, accelerators and delivery assets.
• Drive business development — proposals, executive AI briefings and Dawgen Global thought leadership.

What You Bring

Essential

• 8+ years in management consulting, digital transformation, technology advisory or operations transformation, including leadership of complex client engagements.
• Working command of generative, automation and agentic AI — enough to challenge an architecture.
• A track record of turning technology investment into measured financial and operational outcomes.
• Strong financial analysis, business-case and operating-model redesign skills, and familiarity with AI governance, cyber, data and regulatory risk.
• Executive presence, sound commercial judgement and experience leading multidisciplinary teams.

Advantageous

• Big Four or comparable advisory, strategy consulting, financial-services transformation or AI programme leadership; experience in the Caribbean or comparable emerging markets.

What Success Looks Like

Time to first demonstrable client value; diagnostic-to-sprint and sprint-to-implementation conversion; recurring managed-service conversion; quantified client benefits; implementation quality; client satisfaction; reusable intellectual property; and commercial performance.

Why Dawgen Global

• Build something new. Join as a founding member of a Group built to set the standard for AI transformation in the Caribbean.
• Work where you work best. We welcome both in-office team members at our Kingston headquarters and remote team members, with travel to client sites as engagements require.
• Real problems, real support. Work inside client operations across the region's major industries, alongside specialists in audit, tax, risk, cyber, HR and advisory in 15+ territories.
• Competitive remuneration and a clear path to grow as the Group scales.

About Dawgen Global

Dawgen Global is an independent, integrated multidisciplinary professional services firm with over 24 years serving Caribbean business. Managed centrally from its Caribbean headquarters in Kingston, Jamaica, the firm serves clients across 15+ Caribbean territories in audit and assurance, tax, risk, cybersecurity, IT and digital transformation, HR, M&A, corporate recovery and business advisory. The Forward-Deployed AI Transformation Group works inside client organizations to move artificial intelligence from experimentation to measurable business results.

How to Apply

To speed up the process, please email the following three items together:

• The completed Dawgen Global Employment Application Form — download it here: https://www.dawgen.global/wp-content/uploads/2026/10/Approved-Dawgen_Global_Employment_Application_Form-for-Caribbean-2026-approved-.docx
• Your CV.
• A one-page cover letter describing one transformation you personally moved from concept to measured outcome — the baseline and the result.

Email: opportunities2026@dawgen.com Subject: FDAI-01 — Group Lead / AI Transformation Director — [Your Name]

Please indicate whether you would prefer to work from our Kingston office or remotely. Applications that do not include the completed application form will not be considered. Applications are reviewed on a rolling basis; only shortlisted candidates will be contacted. Dawgen Global is an equal-opportunity employer and appoints on merit; personal information is used only for recruitment, in line with the Jamaica Data Protection Act, 2020.