IT Service Consultant

Dear Reader,

I am a visionary leader with several years of dynamic experience in IT, telecommunications, software development, and cybersecurity. My greatest strength lies in driving transformative change within business environments.

If you’re interested in my services, please feel free to contact me via email at mychitterman@gmail.com or WhatsApp at +1 473 423 1109.

My CV is listed here for your reference:

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IMI CHITTERMAN
La Digue, St. Andrew’s, Grenada W.I.
Email: mychitterman@gmail.com
WhatsApp: +1 (473) 423 – 1109


OVERVIEW

A dynamic and seasoned ICT executive with over 16 years of experience in managing large-scale technology infrastructure projects, ICT policy development, and digital transformation initiatives. I have a proven track record of leading successful World Bank-funded projects, implementing national fiber networks, and spearheading legislative efforts such as the Grenada Data Protection Act of 2023. My extensive work includes directing cybersecurity initiatives, disaster recovery, business continuity strategies, and collaboration across multiple government sectors. With deep expertise in project management, I have led cross-functional teams to deliver innovative, secure, and resilient ICT solutions for the Government of Grenada and across the Caribbean region.


KEY STRENGTHS

  • Strategic ICT Planning & Leadership
  • World Bank Project Implementation & Management
  • Disaster Recovery & Business Continuity
  • Cybersecurity & Data Protection
  • Stakeholder Collaboration & Communication
  • ICT Infrastructure Management
  • Financial Management & Budgeting
  • Procurement & Vendor Management
  • Application & Systems Development
  • ICT Policy Development & Compliance

PROFESSIONAL EXPERIENCE

Chief Information Officer

Government of Grenada | 2010 – Present

  • Led the development and implementation of the Grenada Data Protection Act of 2023, which established national standards for data privacy and compliance. This included:
  • Drafting policy documents, conducting public consultations, and collaborating with legal teams.
  • Establishing the Data Protection Authority responsible for enforcing compliance and managing citizen data protection rights.
  • Team Leader for a 2019 ransomware incident, leading the cybersecurity response that restored government operations. Developed and implemented cyber incident response strategies.
  • Managed the rollout of a national fiber network across three islands, connecting over 480 buildings, including government offices and schools via EduNet, a dedicated fiber network for education.
  • Led the CARCIP Phase 2 Small ICT Grants Distribution, overseeing the distribution of grants to support ICT innovation and development across Grenada.
  • Led the development of the Medium Term ICT Plan (2022-2024), collaborating with the Cabinet Office and the Ministry of ICT to align ICT initiatives with national priorities.
  • Managed budgets for multiple World Bank-funded projects, including DG4R (Digital Governance for Resilience) and CARDTP, securing over USD 15 million in funding.
  • Collaborated with stakeholders, including Digicel OECS, the Ministry of ICT, and government departments, to implement cost-effective ICT solutions such as digitization of government records and the development of EduNet.
  • Led NADMA operational centers annually, ensuring the provision of IT and telecommunication support for disaster recovery and emergency response. Supported the NTRC in establishing a Land Mobile Radio network with the Royal Grenadian Police Force under the 2018 strategic plan.
  • Spearheaded the establishment of the Grenada Data Center, ensuring its integration with national ICT infrastructure and providing secure data storage for government records.

WORLD BANK PROJECT MANAGEMENT

Project Manager & Technical Lead

DG4R (Digital Governance for Resilience) & CARDTP Projects | 2021 – 2022

  • Managed the DG4R and CARDTP projects, leading the drafting of Terms of Reference (TORs) for project components, including the acquisition of a project management firm, development of a new tax system, and digitization of government paper records.
  • Developed business case justifications and cost-benefit analyses for ICT projects, securing USD 15 million in funding for DG4R.
  • Collaborated with government departments and international stakeholders to ensure project alignment with World Bank standards, maintaining consistent communication on project progress and risks.

CYBERSECURITY & DISASTER RECOVERY

  • Led the response to the 2019 ransomware attack that affected government operations. Worked with local and international cybersecurity teams to restore services, strengthen cyber defenses, and prevent future incidents.
  • Developed and maintained disaster recovery plans for critical ICT infrastructure, ensuring continuity of government services during crises.
  • Supported NADMA in executing disaster recovery and emergency communication strategies, including deploying the Land Mobile Radio Network with the Royal Grenadian Police Force.

INFRASTRUCTURE & APPLICATION DEVELOPMENT

  • Managed the deployment and maintenance of ICT infrastructure, including servers, network equipment, and telecommunication systems for EduNet and government offices.
  • Directed the development of several in-house applications, integrating SharePoint Office 365 solutions to automate internal workflows and streamline government operations.
  • Implemented enterprise API integration (SOAP and REST APIs) to support secure and scalable application development within the government ecosystem.

EDUCATION

  • MSc Information Technology – Project Management
    University of Sydney, Australia | 2014–2015
  • Graduate Diploma in Enterprise Software Engineering
    Humber College, Ontario, Canada | 2008–2009
  • BSc Computing and Information Systems
    University of London | 2008–2010
  • Diploma in Computing and Information Systems
    University of London | 2004–2006

CERTIFICATIONS & TRAINING

  • PMP Certification (trained)
  • PRINCE2 – Project Management Certification trained
  • TankU Practice- Japan ( Certified)
  • COBIT – IT Governance Framework (Trained)
  • Advanced SPSS Certification – Organization of Eastern Caribbean States
  • Microsoft Certified Systems Administrator (MCSA) – Exchange 2003 Servers
  • IT Governance – Under the COBIT Framework (Trained)
  • Power BI ( Trained)
  • Data Analytics ( Trained)
  • Mapping GIS with Drones (Trained)
  • Advance Negotiation UNDP ( Trained/Certified)

SKILLS

  • Strategic ICT Planning & Leadership
  • Project Management (PRINCE2, PMP)
  • ICT Infrastructure & Operations Management
  • Cybersecurity & Data Protection Compliance
  • Disaster Recovery & Business Continuity
  • Procurement & Vendor Management
  • Network Infrastructure (LAN/WAN, Fiber)
  • Digital Transformation Leadership
  • Collaboration & Team Management
  • Financial Management & Budgeting

REFERENCES

Reference CategoryNamePositionOrganizationContact Information
Academic and ResearchDr. Lindonne TelesfordAssistant Dean of Graduate Studies, Associate ProfessorSchool of Medicine, St. George’s UniversityPhone: +1(473) 444-4175 ext. 3078
Email: ltelesfor@sgu.edu
Statistical and Data AnalysisJunior AlexisSenior StatisticianCentral Statistical Unit, Government of GrenadaEmail: junior.alexis@gmail.com
Maurice GeorgeSenior IT Technical/Web Master GeneralGovernment of Grenada W.I.Email: info@gov.gd
IT TeamPaul MilletteIT ManagerParliamentary Elections Office, GrenadaPhone: +1(473) 440-2357 / 2698
Email: millettepaul@yahoo.com
ProcurementTerrence VictorSenior Procurement OfficerGovernment of GrenadaPhone: +1(473) 405-7071
Email: terrencevictor@procurement.gov.gd
Jenny AlexanderSenior Procurement OfficerGovernment of GrenadaEmail: jennyalexanderspo@procurement.gov.gd
Advisory and Private Sector ResearchCurlan GilchristAdvisory and Private Sector Research ConsultantEmail: curlangilchrist@gmail.com
Software Development (.NET)Peter EnglishIT ManagerSupreme Court Registry, GrenadaEmail: mypedroe@gmail.com
Professional Work Reference (Consultant)Alice BainPrivate ConsultantEmail: nnaola23@gmail.com

This table format offers a clean and structured way to display your references, making it easy to navigate through different categories. Let me know if you’d like any further refinements!

Terrence Victor Senior Procurement Officer, Government of Grenada (+1 (473) 405-7071)

Some of My work in the recent time ( past 5 years)

Job Duty / ResponsibilityYour Experience / ResponseWorkload Classification
Develops and maintains the ICT strategic plans, business continuity plans, and internal operating processes.Led the development and implementation of strategic ICT policies for the Government of Grenada, including the CARCIP Project and the Grenada Data Protection Act of 2023. Collaborated with the Cabinet Office to direct the Medium Term Plan of 2022 to 2024.Strategic Planning & Leadership
Leads ICT Department operational and strategic planning, including fostering innovation, planning projects, and negotiating the allocation of resources.Managed strategic planning and resource allocation for the rollout of a national fiber network and digitization projects. Collaborated with the Ministry of ICT, Grenada, to create the strategic plan for Cyber Security and the Data Protection Agency.Strategic Planning & Leadership
Develops short and long-range plans covering the resource needs associated with delivery of ICT infrastructure, operations, application, and process support.Planned and executed long-term ICT infrastructure projects, including the establishment of the Grenada Data Center and EduNet, ensuring resource optimization. As CIO (2018-2022), led the collaboration and management of resources to deliver core ICT outputs in Grenada.Strategic Planning & Leadership
Develops department budget and collaborates with relevant executive staff members and other Departmental Managers to complete the department’s budget.Managed budgets for World Bank-funded projects (DG4R, CARDTP) and CARCIP. Planned, negotiated, and managed the budget allocation for the Ministry of ICT (2018-2022), developing quarterly cash flow projections.Financial Management & Budgeting
Provides advice, guidance, and assistance to staff members and end-user areas on matters related to the design, development, and application of automated information systems.Regularly provided advisory services to government departments on digitization efforts, transitioning to electronic records management and developing national ICT systems. Managed vendors and developed systems using SharePoint Office 365/Skybow for internal workflow automation.ICT Support Services
Manages financial aspects of the ICT Department, including purchasing, budgeting, and budget review.Managed financial planning for ICT projects, including procurement of ICT infrastructure and vendor management for large-scale national projects.Financial Management & Budgeting
Develops business case justifications and cost/benefit analyses for ICT spending and initiatives.Developed business cases for DG4R and the national fiber network, securing over USD 15 million in funding. Created more than 20 business cases for various departments and agencies in Grenada.Financial Management & Budgeting
Works closely with key decision-makers/stakeholders to identify, recommend, develop, implement, and support cost-effective world-class ICT solutions for all aspects of the Agency.Collaborated with key stakeholders, including Digicel OECS and government departments, to implement cost-effective ICT solutions such as EduNet and the digitization of government records. Worked closely with the Ministry of Finance in decision-making processes.Stakeholder Collaboration & Communication
Directs and may participate in developing in-house applications, purchasing vendor software, and integrating the applications of either or both.Managed the development and implementation of several software packages, including .NET systems, SharePoint applications, and Windows desktop and web applications.Application & Systems Development
Collaborates with other Departmental Managers to review project(s) status, discuss problem areas, and plan future courses of action.Collaborated with senior managers to review project statuses during the CARCIP and DG4R projects, providing solutions to overcome challenges and ensure timely implementation.Stakeholder Collaboration & Communication
Develops applications programming standards, including project management models, design, development, and maintenance procedures and related protocols.Developed software using a combination of Agile and Waterfall methodologies, based on the ADKAR change management framework. Used enterprise APIs (SOAP, REST) for client-supported systems.Application & Systems Development
Maintains the necessary documentation for the department’s functions.Managed detailed documentation of project milestones, financial records, and compliance protocols for the DG4R and CARCIP projects.ICT Policies & Compliance
Manages the deployment, monitoring, maintenance, development, upgrade, and support of all ICT systems, including servers, PCs, mobile phones, wireless internet devices, etc.Led the deployment of national ICT systems, including EduNet, government network infrastructure, and the digitization of government records. Additionally led deployments across the Caribbean region.Infrastructure & Operations Management
Benchmarks, analyses, reports, and makes recommendations for the improvement and growth of the ICT infrastructure and systems.Provided strategic reports and recommendations for improvements in national ICT infrastructure, including the rollout of fiber optics and secure digital government records management systems.Infrastructure & Operations Management
Oversees provision of end-user services, including help desk and technical support services.As a change management advocate, reinforced the concept of continuous improvement via help desk support and self-development training, ensuring that staff undergo upgrades and training at least twice per year.ICT Support Services
Works with stakeholders to define business and systems requirements for new technology implementations.Collaborated with government departments to define system requirements for the implementation of EduNet and the digitization of government records. Examples include platforms for e-services, e-tax, and e-payment.Stakeholder Collaboration & Communication
Directs research on potential technology solutions in support of procurement efforts.As a practicing statistical officer and researcher, this forms a core part of my responsibilities for evaluating potential technology solutions in procurement efforts.Procurement & Vendor Management
Approves and oversees ICT-specific projects internal to the Agency.Led key ICT projects, including the Grenada Data Protection Act of 2023, CARCIP Phase 2 Small ICT Grants Distribution, and the rollout of a national fiber network.ICT Policies & Compliance
Develops and implements all ICT policies and procedures, including those for architecture, security, disaster recovery, standards, purchasing, and service provision.Developed ICT policies and procedures for the Government of Grenada, including security protocols, disaster recovery plans, and data protection standards under the Grenada Data Protection Act of 2023.ICT Policies & Compliance
Negotiates and administers vendor, outsourced consultant contracts, and service agreements.Negotiated contracts and service agreements with vendors for large-scale ICT projects, including the national fiber network and EduNet.Procurement & Vendor Management
Practices asset management for ICT hardware, software, and equipment.This is core to my daily operations. Without my inventory, then who can I service. Procurement & Vendor Management
Establishes and maintains regular written and in-person communications with the Agency’s executives, department heads, and end-users regarding pertinent IT activities.Provided regular communication to senior management and department heads on ICT activities, including bi-weekly updates on project progress and challenges for World Bank and CARCIP projects.Stakeholder Collaboration & Communication
Keeps abreast of the latest technologies.Regularly updated the government’s ICT infrastructure with the latest technologies, including fiber optics, secure digital records systems, and mobile computing platforms for data capture.Continuous Improvement & Innovation
Liaises and collaborates with the ICT personnel within the Agency (Headquarters, JRCC, and RIFC) in the execution and implementation of the Agency’s projects.Collaborated with key ICT personnel and teams across the government to ensure the successful execution of national ICT projects like EduNet and the national fiber rollout.Stakeholder Collaboration & Communication

Alignment of my past experience to meet the current workload as per the Advertisement.


Workload Summary

Strategic Planning & Leadership:

  • High involvement in defining ICT roadmaps, business continuity strategies, and long-term planning. This includes projects like the Grenada Data Protection Act of 2023, CARCIP, and leading the development of the Medium Term Plan (2022-2024).
  • Involvement in planning the Cyber Security and Data Protection strategic plan.

Financial Management & Budgeting:

  • Moderate to high responsibility, including creating and managing budgets for World Bank-funded projects like DG4R and CARDTP, as well as managing the budget for the Ministry of ICT from 2018-2022.
  • Responsibilities include financial oversight, cost-benefit analysis, and quarterly cash flow planning.

Infrastructure & Operations Management:

  • High workload in managing day-to-day ICT operations, ensuring uptime and stability of systems, including national ICT infrastructure, EduNet, and government networks.
  • Led the deployment and upgrade of ICT systems, not just in Grenada, but also regionally.

ICT Policies & Compliance:

  • Significant focus on creating, implementing, and maintaining compliance with ICT policies, security protocols, disaster recovery plans, and data protection standards under the Grenada Data Protection Act.
  • Involvement in aligning policies with global best practices and ensuring data privacy and security.

Application & Systems Development:

  • Moderate workload, with a focus on developing and integrating software solutions such as SharePoint applications, Office365 workflows, and .NET systems.
  • Utilized Agile and Waterfall models for software development, managing API integration (SOAP, REST).
  • Develop .Net web base application for various government agencies. Include of the Cabinet Record management system for Grenada. Web Based system with securely embedded PDF file employing .NET technologies, C#, and the MS SQL server for storage of meta data.
  • Several other small .NET application within the Public Sector of Grenada.

ICT Support Services:

  • Significant focus on maintaining help desk services and technical support across departments, ensuring reinforcement through regular staff upgrades and continuous improvement.
  • Help desk management is oriented towards service delivery and user satisfaction.

Procurement & Vendor Management:

  • Moderate involvement in managing vendor contracts, procurement processes, and external service agreements.
  • Successfully negotiated contracts for large ICT projects, including fiber network installations and EduNet.

Stakeholder Collaboration & Communication:

  • High level of collaboration with internal teams, ministries, and key stakeholders (e.g., Digicel OECS, Ministry of Finance) to align ICT initiatives, solve problems, and manage project implementations.
  • Regular updates to senior management, ensuring clear communication of progress and challenges.

Disaster Recovery & Business Continuity:

  • Essential focus on maintaining critical ICT services and preparing for potential disruptions. As team leader for a cyber-related ransomware incident in 2019 that affected the government, I led response and recovery efforts to restore operations.
  • Additionally, I led NADMA operational centers annually for IT and telecommunications, supporting the NTRC to establish a Land Mobile Radio Network in conjunction with the Royal Grenadian Police Force, as part of the 2018 strategic plan for disaster readiness and emergency response.

Continuous Improvement & Innovation:

  • Ongoing focus on adopting the latest technologies, such as fiber optics, secure digital records, and mobile computing platforms for improving existing systems and delivering innovative solutions.
  • Promoting a culture of technological advancement and continuous system enhancement.

Skills Sets

#Project Management # Project Portfolio Management #WorldBank Procurement # Software Implementation #Digtial Change Management #Digtial Transformation Management #Cyber security support #IT Networks ( Telecommunication and LAN) #.NET web hosting ( Sever 2000+ to all current version) #Windows Users #MS SQL Server # Power BI #SPSS #R Studio #SharePoint(office365) Skybow Forms Designer #Lighteening Tools # DocuEase #IT Adoption Training and Support #Remote Assistance #Chief Information Officer #Office365 Admin #OneDrive #MS Teams #Small Business Business Platforms #Drone Imagery (Pix4D,Metashape) #MS Excel #MS SQL Servers ( Admin, Management, Advance developer)

Here’s a scoring matrix based on the qualifications and skills mentioned in the job description and your CV:


Scoring Matrix for Qualifications and Skills

Qualification/Skill AreaWeight (%)Max Points (Out of 10)Evaluator ScoreComments
ICT Infrastructure Planning & Implementation15%108Strong experience with national fiber network rollout and EduNet, but more details needed on specific technologies and protocols (LAN/WAN, voice/data).
Strategic Planning and Leadership15%109Excellent leadership on large-scale projects like DG4R and CARCIP. More detail on long-term strategy and innovation could further boost this section.
Vendor Management & Procurement10%107Procurement experience mentioned but could include specific outcomes (RFPs, cost savings). Strong vendor relationship management.
Cybersecurity & Systems Security10%108Good cybersecurity leadership (e.g., ransomware response), but more emphasis on proactive measures and recent technologies would strengthen this area.
Disaster Recovery & Business Continuity10%108Demonstrated experience with NADMA and cyber incident recovery, but could expand on detailed plans or frameworks used for business continuity.
Financial Management & Budgeting10%108Managed large budgets for World Bank projects, with some details provided. More concrete examples of financial oversight and outcomes are needed.
Project Management (PMP, PRINCE2)10%109PRINCE2 and PMP training is strong, with a history of managing complex ICT projects. Completing PMP certification could enhance this section further.
Collaboration & Stakeholder Engagement10%109Strong examples of collaboration with government entities and private sector. Could expand on engagement outcomes and alignment with organizational goals.
Application & Systems Development5%108Experience with SharePoint and .NET development mentioned. Could be enhanced by elaborating on software development standards and methodologies used.
Certifications & Continuing Education5%107Solid certifications (PRINCE2, COBIT) but more recent certifications or completed PMP would boost this score.
Communication & Reporting5%109Excellent communication and reporting skills, particularly in project updates to senior management and stakeholder alignment.
Innovation & Continuous Improvement5%108Regular updates on technology adoption and process improvements mentioned. More specifics on how these innovations impacted efficiency or security would help.

Total Score:

Using the weights and scores:

| Weighted Score = (Weight * Score) for each section.
For example, for ICT Infrastructure Planning:
= (15% * 8) = 1.2

| Total Maximum Weighted Score = 10
= Sum of all weighted scores


Evaluator Comments:

Your CV performs very well across a range of criteria, particularly in leadership, project management, and stakeholder engagement. To further enhance your application, focusing on more quantifiable outcomes in procurement, cybersecurity, and certifications will strengthen your overall profile.

Here’s a Glossary of Terms for your CV, providing clear definitions for the technical and professional terms used:


Glossary of Terms

  • ADKAR Model: A change management framework that focuses on five key elements for successful change: Awareness, Desire, Knowledge, Ability, and Reinforcement.
  • Agile Model: A project management and software development methodology that promotes continuous iteration and collaboration, delivering small, functional segments of a project.
  • API (Application Programming Interface): A set of tools and protocols that allow different software applications to communicate with each other. Common types include SOAP (Simple Object Access Protocol) and REST (Representational State Transfer).
  • Business Continuity Plan (BCP): A strategy that outlines how a business or organization will continue operating during and after a disaster or major disruption.
  • CARCIP (Caribbean Regional Communications Infrastructure Program): A World Bank-funded initiative aimed at improving communication infrastructure in the Caribbean region.
  • Change Management: The structured approach to transitioning individuals, teams, and organizations from a current state to a desired future state, minimizing resistance and disruption.
  • COBIT (Control Objectives for Information and Related Technologies): A framework for developing, implementing, monitoring, and improving IT governance and management practices.
  • Cybersecurity: Measures and practices taken to protect systems, networks, and data from digital attacks or unauthorized access.
  • DG4R (Digital Governance for Resilience): A World Bank project aimed at strengthening the digital governance framework of an organization to enhance resilience.
  • Disaster Recovery (DR): A process or set of procedures to recover and protect an organization’s IT infrastructure following a disaster.
  • EduNet: A dedicated fiber network in Grenada designed to connect schools and educational institutions, providing secure and high-speed internet access.
  • Enterprise API: A set of protocols and tools used to build software for large-scale enterprise applications. SOAP and REST are commonly used in enterprise APIs.
  • ICT (Information and Communication Technology): The infrastructure and components that enable modern computing, including telecommunications, computers, software, and networks.
  • ICT Governance: The framework and processes used to ensure that ICT resources are managed in alignment with an organization’s goals and objectives.
  • LAN (Local Area Network): A computer network that connects devices within a limited geographical area, such as a building or campus.
  • PMP (Project Management Professional): A globally recognized certification for project managers, issued by the Project Management Institute (PMI), indicating proficiency in managing and leading projects.
  • PRINCE2 (PRojects IN Controlled Environments): A structured project management method and practitioner certification program emphasizing dividing projects into manageable stages.
  • Procurement: The process of finding, acquiring, and buying goods, services, or works from an external source, often via a tendering or competitive bidding process.
  • RFP (Request for Proposal): A document that solicits proposals from suppliers, detailing the project’s requirements and scope. It is used during procurement to evaluate potential vendors.
  • RFQ (Request for Quotation): A business process in which an organization invites suppliers to provide pricing and terms for specific goods or services.
  • SaaS (Software as a Service): A software distribution model in which applications are hosted by a service provider and made available to customers over the internet.
  • SharePoint: A web-based collaboration platform used for document management, storage, and team collaboration.
  • SOAP (Simple Object Access Protocol): A messaging protocol that allows programs running on different operating systems to communicate with each other over a network.
  • Stakeholder Engagement: The process of involving people who may be affected by or have an influence on the outcomes of a project or initiative.
  • Strategic Planning: The process of defining an organization’s strategy, direction, and decision-making to allocate resources and pursue specific goals.
  • WAN (Wide Area Network): A telecommunications network that extends over large geographical distances, typically connecting multiple local area networks (LANs).

When applying for a job with a long list of duties, especially if it seems like the position is being established for the first time, it’s important to ask the right questions to ensure you have a clear understanding of the role and the organization’s expectations. Here’s a list of questions you might consider asking:


Questions about Role Clarity and Expectations:

  1. How is the success of this position measured?
  • It’s important to know how your performance will be evaluated. Are there specific KPIs (Key Performance Indicators) or goals?
  1. Is this a newly created position, or are you replacing someone?
  • If it’s a new role, it’s important to understand how the expectations were developed and if there is flexibility in shaping the role. If replacing someone, ask about their challenges and successes.
  1. What are the top priorities for the first 6 to 12 months in this role?
  • This helps you gauge what the organization expects you to focus on initially and whether those priorities are realistic.
  1. How many of these responsibilities are already in place, and how many will require building from the ground up?
  • Some tasks might already be ongoing, while others might need to be created from scratch. This question helps you understand the scope of the work.
  1. Are there any immediate challenges or roadblocks I should be aware of in executing these duties?
  • This can help you uncover any potential issues with resources, processes, or organizational support.
  1. Can you describe the structure of the team and the resources that will be available to support these duties?
  • You need to know if you’ll be working with a team, external vendors, or alone. This helps clarify if the workload is manageable.
  1. How do you prioritize these numerous responsibilities in day-to-day operations?
  • This helps to uncover whether there is an understanding that all duties cannot be handled simultaneously and if there is flexibility in workload management.
  1. What is the expected balance between strategic leadership and hands-on execution in this role?
  • If the role involves both leadership and execution, it’s important to understand the expectations for how much time should be spent on each.
  1. How much autonomy will I have in making decisions related to these responsibilities?
  • If you’ll have significant responsibilities, you need to know if you’ll have the authority to make key decisions or if you’ll be required to escalate every issue.
  1. How does this role fit within the broader organizational structure?
    • Understanding how your position integrates with the rest of the organization can help you navigate internal processes and identify key stakeholders.

Questions about Resources and Support:

  1. What resources are currently in place to support the execution of these duties?
    • This can include technology, budget, staff, or external consultants.
  2. Is there an allocated budget for training, upskilling, and professional development?
    • If you’re expected to manage diverse duties, understanding whether the organization supports your growth is crucial.
  3. Will I have access to dedicated administrative or technical support?
    • Knowing whether you have support staff or technical experts to assist you can help determine whether the workload is feasible.
  4. Are there any planned system upgrades or policy changes that might impact the duties of this role?
    • You’ll want to know if there are any upcoming changes that could affect your responsibilities, especially if you’ll need to adapt quickly.

Questions about Job Scope and Workload:

  1. Given the extensive list of duties, is there any flexibility in adjusting the role as we assess the workload over time?
    • Asking this shows that you are thinking critically about the job and want to ensure you can deliver quality work without burnout.
  2. How do you ensure workload distribution is balanced, especially in this wide-ranging role?
    • This helps assess if they have realistic expectations or a process for prioritizing tasks.
  3. Are any of these duties shared with other departments or roles, or will I be solely responsible for all listed tasks?
    • Knowing if you’ll share responsibilities with other teams can help you assess if the workload is reasonable.

Questions about Strategic Vision and Organizational Culture:

  1. How does this role contribute to the long-term strategic vision of the organization?
    • Understanding the bigger picture can help you align your work with the organization’s goals.
  2. What is the culture like when it comes to innovation, change management, and adaptability?
    • Since the duties indicate a broad and potentially evolving role, knowing how open the organization is to change can help you understand how much room you’ll have to innovate.
  3. How does the organization support work-life balance, especially in a role with such a comprehensive list of responsibilities?
    • This helps you gauge if the organization values work-life balance and has systems in place to prevent burnout.

Questions about Career Growth and Development:

  1. What opportunities for career progression exist for this position?
    • If the role involves significant responsibility, it’s important to know what opportunities exist for future growth and advancement.
  2. Will there be opportunities to delegate tasks as the role grows or expands over time?
    • If this is a first-time position, understanding how the role might evolve and whether you’ll eventually have support staff is critical.

By asking these questions, you can clarify the scope of the job and ensure that both you and the employer have aligned expectations. It will also help you assess whether the position offers the support and resources you need to succeed.

Here’s a tailored cover letter focused on your application for a CARICOM position and emphasizing how your experience aligns with the job description:


Imi Chitterman
La Digue, St. Andrew’s, Grenada W.I.
Email: mychitterman@gmail.com
WhatsApp: +1 (473) 410-7767
[Date]

Hiring Manager
[CARICOM Secretariat]
[Address]
[City, Country]

Dear [Hiring Manager’s Name],

I am writing to express my interest in the [Job Title] position at the CARICOM Secretariat. As an experienced ICT professional with over 15 years of hands-on leadership in managing large-scale government projects and regional initiatives, I believe my background strongly aligns with the role’s responsibilities in supporting CARICOM’s impact on regional digital transformation and ICT advancement.

In my current role as Chief Information Officer for the Government of Grenada, I have led a number of high-impact ICT projects, many of which have required cross-regional collaboration and alignment with international standards. Notably, I was the technical lead in the rollout of Grenada’s national fiber network, which connected over 480 buildings across three islands, including government offices, schools, and healthcare institutions. This large-scale project directly supported the government’s goal of improving national connectivity, and it is this kind of strategic leadership I aim to bring to CARICOM.

Furthermore, I have led key World Bank-funded initiatives, such as the Digital Governance for Resilience (DG4R) Project and CARCIP (Caribbean Regional Communications Infrastructure Program). These projects were instrumental in enhancing Grenada’s digital governance framework and increasing the country’s capacity for regional ICT integration. My role involved not only the implementation of ICT policies but also the management of financial resources, stakeholder engagement, and the development of robust procurement processes—all crucial to executing multi-country initiatives like those at CARICOM.

Some of my core achievements that align with the job description include:

  • Strategic ICT Planning & Governance: Led the implementation of the Grenada Data Protection Act of 2023, ensuring compliance with international data protection standards while fostering regional digital collaboration.
  • Cross-regional Collaboration: Worked extensively with stakeholders from various Caribbean nations through projects like CARCIP, ensuring alignment with CARICOM’s ICT goals.
  • Disaster Recovery & Business Continuity: Directed the response to the 2019 ransomware attack on government systems, which strengthened my understanding of regional cybersecurity frameworks, a key focus area for CARICOM.
  • Vendor & Procurement Management: Managed procurement processes for large-scale ICT projects, ensuring cost-efficiency and compliance with regional standards, which will be invaluable in supporting CARICOM’s ICT development.

The opportunity to work within CARICOM, driving impactful digital initiatives across the Caribbean region, is a natural extension of my career aspirations. I am particularly motivated by the chance to leverage my experience in ICT infrastructure, governance, and cross-country collaboration to contribute to CARICOM’s mission of strengthening the region’s digital future.

Thank you for considering my application. I am excited about the potential to contribute to your team and am confident that my skills and experiences will add significant value. I look forward to discussing how my background can support CARICOM’s ongoing ICT and digital transformation efforts.

Sincerely,
Imi Chitterman


This cover letter highlights your key achievements and focuses on the CARICOM Secretariat’s mission, positioning you as a strong candidate for their digital transformation initiatives. Let me know if you’d like to make further adjustments!

Based on the document provided, here’s a tailored Table of Contents (TOC) for your CV:


Table of Contents

  1. Cover Letter…………………………………………………………………………………………….1
  • Introduction to the Role
  • Key Achievements
  • Conclusion
  1. Overview…………………………………………………………………………………………………2
  • Summary of Experience
  • Key Strengths
  1. Professional Experience………………………………………………………………………….3
  • Chief Information Officer, Government of Grenada
  • World Bank Project Management
  • Cybersecurity & Disaster Recovery
  • Infrastructure & Application Development
  1. Education………………………………………………………………………………………………..6
  • Academic Qualifications
  • Certifications & Training
  1. Skills………………………………………………………………………………………………………..7
  • Technical Skills
  • Project Management Skills
  1. References………………………………………………………………………………………………8
  • Academic and Research References
  • Statistical and Data Analysis References
  • IT Team References
  • Procurement References
  • Advisory and Private Sector Research Reference
  • Software Development (.NET) Reference
  • Professional Work Reference (Consultant)
  1. Workload Alignment………………………………………………………………………………..9
  • Alignment of Past Experience to Job Advertisement Workload
  • Workload Classification Summary
  1. Scoring Matrix for Qualifications and Skills……………………………………………….10
  • Detailed Qualifications
  • Scoring Criteria
  1. Glossary of Terms…………………………………………………………………………………..11
  • Key Terms and Definitions Related to ICT and Project Management
  1. Questions for Clarification………………………………………………………………………12
  • Role Expectations and Resources
  • Strategic and Operational Questions
  1. Disclaimer…………………………………………………………………………………………….13
  • Use of AI Assistance

This TOC offers a structured layout for your CV, making it easy to navigate the various sections. Let me know if you’d like to make any further adjustments!

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