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WORC ID: T2B4S4

Regional Head of Retention Business

Digicel Cayman Ltd.
Salary
KYD$85,000 - KYD$88,560 Per Annum (paid Monthly)
Location
North Side
Work Type
Full-time
Hours/Week
40
Education
Not specified
Experience
7-8 Years

Job Description

The retention manager will lead all activities related to contract renewals across GSM and ICT services for an assigned client base. This individual will be accountable for renewal performance, customer satisfaction, retention strategy execution, and year-on-year revenue preservation and growth. The role requires strong ownership of data accuracy, forecasting, renewal pipeline management, account relationship development, and the delivery of an exceptional customer experience. The retention manager will drive the timely preparation of renewal data, pre- and post-renewal analysis, and cross-functional engagement with sales, service, finance, and product teams. This person will also lead the company’s retention strategy, directly engage clients where necessary, and steward high Net Promoter Score (NPS) performance. Success will be defined by delivering double-digit retention improvements, increased customer satisfaction, accurate renewal forecasting, and being an influential contributor to a high-performance, customer-obsessed team culture. The retention manager will also oversee the strategic conversion of existing BTC customers in Bermuda from copper-based services to fibre solutions, ensuring a smooth migration experience and supporting long-term customer retention.

Main Duties and Responsibilities

  • Lead the achievement of all renewal objectives inclusive of renewal targets, revenue

retention, churn reduction, customer satisfaction, and client engagement.

  • Manage and execute all contract renewals for GSM and ICT services across the assigned

client base.

  • Prepare renewal data monthly, maintaining 100% data accuracy and visibility for internal

stakeholders.

  • Provide detailed pre- and post-renewal analysis to support strategic decision-making,

customer engagement, and forecasting accuracy.

  • Perform weekly reviews with the sales team to align renewal pipeline, risks, opportunities,

and client action plans.

  • Lead and coordinate the conversion of existing BTC customers from copper-based services

to fiber solutions, ensuring a seamless transition, minimal service disruption, and strong customer engagement throughout the migration process.

  • Create, lead, and continuously optimize the retention strategy for Digicel Business.
  • Serve as the “client ambassador” internally by engaging and coordinating with service,

finance, product and other support functions to execute client-visible improvement plans.

  • Where necessary, directly engage with clients to support renewal negotiations, address

service concerns, or strengthen relationship outcomes.

  • Lead and manage the company’s client Net Promoter Score (NPS) program, ensuring

actions are taken to improve customer satisfaction and close the loop with clients.

  • Develop high-quality renewal proposals and propositions that support customer needs and

reinforce long-term partnerships.

  • Establish and grow “win/win” client relationships, identifying client coaches and champions

to support mutual success.

  • Commit to and adopt sales metrics including: 100% on-target rolling average renewal

performance, 100% data accuracy

  • Maintain 100% compliance with sales KPI reporting, cadence, Sales Process, and

performance-to-target reporting. Academic qualifications and experience required for job (qualifications will be considered):

Education & Experience

  • Bachelor’s degree in business administration or related discipline with a minimum of 5 years

retention management, sales, or account management experience within the telecommunications and/or technology industries.

  • OR 7 years working in a commercial sales or account management role and experience

within the telecommunications and/or technology industries.

  • Demonstrated renewal or sales target achievement/overachievement required.
  • Enterprise, corporate, and/or SME relationship experience in their market preferred.
  • Experience with sales methodologies such as Target Account Selling, Salesforce

methodology, Miller Heiman, or value-based selling preferred.

  • High standard of written communication, Microsoft Office proficiency, and strong market

language skills required.Page 3 of 3

  • Excellent communication and presentation skills across diverse client audiences. High

emotional intelligence and strong listening skills are required.

  • Focused, passionate, and relentless in achieving goals while collaborating across internal

and external teams to enable shared success. A “win/win” mindset is essential.

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. 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, conduct sales reviews, and lead customer interventions. Work Environment: Hybrid model with regional office work The salary range will be KYD $85,000 – KYD $88,560 per annum depending on qualifications, knowledge and experience. Benefits as deemed by law. Working hours: 40 Mon – Friday 8am to 5pm

Interested in this role?

5 days remaining

Details

Positions1

Timeline

PostedMarch 27, 2026
Start DateMarch 27, 2026
Closing DateApril 10, 2026