Regional Head of Sales

Digicel Cayman Ltd. is seeking a full time Regional Head of Sales The purpose of this role is to lead, develop and motivate the Digicel Business sales & deliver new revenue streams via building an ICT business for Digicel Cayman and to support the Digicel Business teams across the Atlantic region in Cayman, BVI and TCI. To achieve growth and revenue objectives as an integral part of the overall Digicel Cayman and the wider Atlantic Region.

Main Duties and Responsibilities

• Formulates, implements, and delivers strategic sales plans that align with the short- and longterm objectives of the company.
• Lead the strategy definition and new product development process of the business in GSM and ICT.
• Deep experience in maintaining relationships in the boardroom of client companies essential.
• Ability to articulate complex commercial propositions to CXO level customer representatives.
• Provide and communicate weekly, monthly and quarterly updates, revisions and modifications to the plan.
• Build technical plans for customer presentations and proposals.
• Work with international carriers for to propose MPLS network development.
• Meet or exceed Sales Objectives for the business unit.
• Defines and manages the monthly, quarterly and Annual Sales Objectives for all of the sales personnel and establishes compensation plans (along with HR) for all sales personnel including salary structures, commission, bonus and incentive plans.
• Execute the annual sales plan by coaching, guiding and motivating the associated sales teams. Serves as a resource for the development of individual action plans
• Provides Career Development based on an assessment of individual skills and aspirations.
• Leads the sales team in the development of new business opportunities.
• Provides senior level sales expertise where necessary, including negotiations and closing on large or complex accounts.
• Design, plan and maintain Operational Expense Budgets and Inventory Control Plans to allow the business to operate lean and efficiently.
• Ensures that processes and systems exist and are maintained in order to provide timely and accurate reporting of Sales progress and results.
• Flexibility and openness to perform additional and different duties as the business demands.

Academic qualifications and experience required for job (qualifications will be considered):

Education & Experience

• Degree level qualification in directly related subject and minimum 10 years directly related working experience in telecoms business sales environments, of which minimum 5 years in senior management roles.

OR

• 10 years directly related working experience in telecoms business sales environments, of which minimum 5 years in senior management roles
• Familiarity with Telecommunications networking and computing technologies a must have.
• Proficient in the sales of Mobile Internet, Broadband and fixed Internet products and service plans.
• Ability in assessing skill levels within a sales team and providing appropriate coaching and career development
• Proven sales experience with all sales channels including reseller, distributor and end-user.
• Extensive selling skills with a proven track record in Consumer, Enterprise, SMB and Government.
• Computer literate with MS Excel, PowerPoint, Word, Project Management software.
• Excellent written and verbal English communication and interpersonal skills.
• Customer focused influential and a strong negotiator.
• Results oriented and accountable for sales goals and targets with a strong commitment to succeed.
• Strong motivator in assembling and developing sales teams.
• Highly organized with effective time management skills.

Functional Skills

• Strategic and mindset with strong business acumen.
• Excellent stakeholder management across commercial, finance, and technology functions.
• Ability to manage multiple priorities and deliver under tight deadlines.

Working Condition: (e.g. abnormal hours, overtime, etc. Reporting Line: Reports directly to the Regional Head of DB with regular interaction and collaboration with Group DB, and both Market and Regional Leadership. Geographical Scope: Oversight across all Atlantic Region markets — Cayman Islands, Bermuda, British Virgin Islands, Turks & Caicos Islands. Travel Requirements: Frequent in-market travel (40–60%) to support execution, coach local teams, conduct sales reviews, and lead customer interventions. Work Environment: Hybrid model with regional office work, remote coordination, and extensive market fieldwork (customer visits, partner engagement, on-ground sales support). Team Structure: Leads a matrixed team of regional sales leads and collaborates closely with market-level sales managers and operational teams. Annual Salary Range KYD$90,000.00 – KYD$110,000.00 Working hours: 40 - 45 Mon – Friday 8am to 5pm