Programme Manager

Reports to: Executive Director of one2one Cayman Islands

one2one Cayman Islands is a non-profit organisation whose mission is to provide children, youth, and young adults with opportunities to thrive and grow through sustainable mentoring relationships to make positive contributions in our society.

Our programmes provide support, guidance, and encouragement to young people, helping them build resilience, self-confidence, and life skills to achieve their full potential.

Position Objective

The Programme Manager delivers match management services related to recruiting, screening, matching and monitoring mentoring relationships. The post holder will be responsible for developing and delivering innovative mentoring programmes and strengthening community partnerships. The successful candidate will combine strategic thinking with practical delivery, ensuring that one2one programmes are impactful, youth-focused, and aligned with the Cayman Islands' community needs.

Key Responsibilities

Case Management (60%)

• Supervise a caseload of 80–100 matches comprised of mentors, mentees and parents/caregivers with the goal of creating impactful and sustainable mentoring relationships

• Conduct recruitments, orientations, and interviews for mentees, mentors, parents/caregivers referred to mentoring programmes

• Engage in the match management process by performing and overseeing screenings, assessments, training, supervision, recognition and match closure activities

• Provide regular monitoring and support to mentoring matches to ensure child safety, match quality, positive youth development outcomes, and mentor satisfaction

• Develop and implement case management plans that respond to mentees' needs, including appropriate referrals, advocacy, and collaboration with partner agencies

• Respond promptly and professionally to challenges and safeguarding concerns, ensuring compliance with local safeguarding legislation and the organisation's safeguarding policies

• Maintain accurate and confidential database records, ensuring compliance with internal policies and Cayman Islands legal requirements

• Assist with other administrative duties and activities as needed

Programme Development & Delivery (30%)

• Design and implement individual and group mentoring programmes, workshops, and events that respond to the identified needs of the target population

• Coordinate and deliver orientation and educational sessions for mentors, mentees, and parents/guardians

• Evaluate programme effectiveness using qualitative and quantitative data to include in fundraising proposals and operational reports

• Ensure programmes are culturally relevant, evidence-based, and aligned with one2one's mission of positive youth development

Community Outreach & Partnerships (10%)

• Represent one2one Cayman Islands at community events, schools, and stakeholder meetings to raise awareness and promote mentoring services

• Build strong partnerships with schools, churches, community organisations, and government agencies to broaden reach and increase mentoring relationships

Qualifications, Experience & Skills

• Bachelor's degree in Human and Social Services, Social Work, Psychology, Education, Children and Youth Development or related field

• 3–5 years of experience in programme management, youth development, or social services

• Experience in case management, safeguarding, or child protection preferred

• Strong organisational skills with the ability to work independently, as one2one operates in a primarily virtual environment

• Strong interpersonal skills

• Excellent verbal and written communication skills

• Sound decision-making skills to inform the match management process

• Strong understanding of the Cayman Islands' cultural and community landscape

• Proven track record of community outreach, partnership building, and programme delivery

• Ability to work flexible hours including weeknights, occasional weekends and travel across districts in Grand Cayman as required

• Proficiency in MS Office, including Word, Outlook, Excel, and PowerPoint is essential

• Driver's licence is required

Job Details

• Location is hybrid, combined remote working and community locations

• Work week is 45 hours per week as per the CI Labour Act

• The working schedule is dynamic as per the needs of the organisation. Weekends, evenings, holidays and public holiday hours should be expected

Benefits

• Salary Range CI$4,500 – CI$5,500 per month based on education and experience

• Health insurance, pension contributions as per the CI Labour Act

• Annual vacation as per the CI Labour Act

All eligible qualified Caymanians and others legally resident to work are encouraged to apply by sending your CV and 1 professional reference to boardoperations@one2one.ky by September 25th, 2026. WORC ID: R4M8G