Our IT director came into this Caribbean insurance company to help lead their digital transformation through insurance tech implementation and mentoring.

Company Profile

A leading insurer operating in the Caribbean. They boast a $75m Gross Written Premium with 220 staff operating in Jamaica, Barbados, and Turks & Caicos. Their vision is to evolve into a customer-centric, digitally transformed pan-Caribbean insurer. This transformation is anchored in leveraging insurance tech innovations and reimagining straight-through process automation, digital self-service, and partner ecosystems. By integrating these transformative IT strategies for insurance, they aim to reduce expenses, enhance scalability, expedite market innovations, and facilitate M&A activities.

While technology plays a pivotal role in their growth, reshaping their core to become a dynamic, fully-automated, scalable digital innovator in the insurance sector is paramount. Some technological enablers have been identified, but the journey towards this insurance company digital transformation is still in its infancy.

CEO’s Mission

The company’s growth had stagnated due to conventional operational methods and technology hindering its innovative potential. Their existing setup, although competitive, posed challenges to their ambitious pan-Caribbean expansion goals. The solution? Bringing on board an interim CIO with deep expertise in insurance and insure tech from outside the local market. This would infuse the company with the knowledge needed to catalyse their transformation and bridge the existing gaps in senior leadership.

CIO’s Objectives

The primary engagement involved an interim CIO role to:

  • Initially, Craft the IT strategy and roadmap, emphasising the role of IT in insurance development.
  • Spearhead the organisational transformation strategy.
  • Then, offer strategic and operational guidance to their IT, change, and data analytics teams.
  • Mentor their IT manager, grooming him for a future CIO role.
  • Given the novelty of such an extensive program, setting realistic expectations and skill-building became crucial.
  • Finally, as the Director delved into the technology strategy, it became evident that there was a broader business change agenda to address, encompassing business strategy definition and organisational design elements.

What the Director did 

Provided Strategic Leadership, Engaging the Board to Define the Transformation Agenda 

The IT Director reviewed the organisational aspirations and structured them into delivery pillars with clear business outcomes, each supported by technology and organisational change activities.  This was achieved through a series of facilitated workshops and the use of structured models. 

The Director worked with the executive team and the board to gain alignment, which was initially not present, and a funding agreement for the transformation programme. 

Defined the Transformation Roadmap and Implementation Plans. 

The Director defined the transformation roadmap, moving away from the traditional “big bang” expectation to a faster-to-value, lower-risk approach involving an innovative greenfield start-up.   

Resourced and Initiated Programme & Project Delivery 

The Director recruited the core programme team, overseeing the implementation of good governance.  This required expediency, persuasion and tenacity on the associate’s part to go outside the Caribbean market to acquire the necessary skills.  He provided leadership and guidance to an inexperienced change team in the interim in order that the programme was able to continue to make progress. 

Sourced and Procured Key Technologies

The Director reviewed the procurement process to date and the selected vendors.  He used his industry knowledge, understanding of the client’s business and insurance tech insights to conduct a revised procurement process that would give the client a good view of the business possibilities while offering a choice of viable suppliers. 

Designed a Bespoke Development Plan for the Senior IT Manager 

The Director built the structured development path around the individual’s development needs. It included the necessary maturation of the IT function and the needs from the transformational programme. They then, performed the departmental due diligence using industry-standard models. In this case, he used CoBIT, and he benchmarked the requirements of a modern CIO using skills models like the Skills Foundation for the Information Age. The plan emphasised that 70% of learning comes from ‘doing’, 20% from colleague support, and 10% from professional training.


The Results

  •  There is an agreed framework for the transformation which is understood within the organisation which relates the transformational activities to the strategic goals of the organisation 
  • Defined technology and ’non-technology’ deliverables that together will achieve the desired transformation, with clear ownership. 
  • Avoided an expensive mismatch between vendor and customer, digital aspirations and traditional ‘does everything’ monolith, instead engaging a supplier with a clear match between their capabilities and the client’s strategic needs and digital aspirations. 
  • IT maturity assessment complete and development plan in place with a clear training plan, developmental activities and senior-level support in place.