Careers at one2one

We are a Non-Profit Organization on a mission to empower youth and young adults to thrive and make positive contributions to our society. Formerly known as Big Brothers Big Sisters of the Cayman Islands, our organization has a rich history of fostering sustainable mentoring relationships that have a lasting impact on the lives of young individuals.

At one2one, we believe that every young person deserves the opportunity to reach their full potential, regardless of their background or circumstances. Our dedicated team of professionals and volunteers work tirelessly to provide guidance, support, and mentorship to help young people unlock their talents and achieve their dreams.

If you are passionate about making a difference in the lives of youth, and if you share our commitment to building a brighter future for the Cayman Islands and beyond, then we invite you to explore the exciting career opportunities we have to offer. Join us in our mission to create a world where every young person has the support they need to succeed and thrive. Your journey towards a rewarding career with purpose starts here at one2one.

Vacancies

Executive Director

The one2one Cayman Islands is a Non-Profit Organisation whose mission is to provide children, youth, and young adults opportunities to thrive and grow through sustainable mentoring relationships to make positive contributions in our society.

Position Objective: The Executive Director reports directly to the Board of Directors. The post holder is responsible for the overall leadership and strategic plan execution for the agency. Main responsibilities include the development and coordination of mentoring programmes, securing sustainable funding sources and staff management.

Primary Responsibilities

  • Manages the day-to-day operations of the agency in alignment with Agency standards and International best practices.

  • Provides Supervision to 1—2 case managers who are responsible for the delivery of mentoring programmes and services.

  •  Manages the Support Volunteer programme to address auxiliary services.

  • Manages and ensures a system for quality assurance and youth protection consistent with the policies and requirements of the Cayman Islands legislation.

  • Develops and coordinates new programmes and initiatives which respond to the emerging needs of children, youth, and young adults in the Cayman Islands.

  • Works closely with the Board of Directors Finance team by providing programmatic inputs for the annual budget preparation, oversees and controls expenditures within the approved operational budget. 

  • Prepares operational reports for the Board of Directors, which include programmatic progress, challenges, and contingency plans.

  • Proactively ensures that the organisation develops strong long-term relationships with individuals, stakeholders, and corporate donors/funders.

  • Identifies sources for funding and prepares proposals or applications for grants and sponsorships. 

  • Oversees all public relations campaigns, advertising and public relations activities for fundraisers and volunteer recruitment activities.

  • Oversees communication and marketing of the agency and ensures that visibility and promotion of the agency are aligned with the organisation's vision, mission, and values. 

  • Actively participates in the organisation’s growth through attracting, hiring, retaining, developing, and leveraging staff talent to perform at high-quality levels. 

  • Engages in the performance management process, which includes ongoing monitoring and an annual performance review; ensures ongoing training and professional development opportunities are made available to staff. 

 Qualifications and Skills

  • Master’s Degree with 3-5 years of experience or Bachelor’s degree with 5–7 years’ experience in Social Services/Human Services is required; certification or experience in business management would be an asset. 

  • Experience in programme development and coordination is required.

  • Strong organisational skills are required for this position.

  • Excellent interpersonal and communication skills.

  • Experience in non-profit or small business management would be an asset. 

  • Excellent written and verbal communication skills and public speaking skills to develop and deliver presentations related to funding and programmes are critical. 

  • Strategic thinking, business savvy, data-driven decision-making, sound problem-solving skills, ability to assess situations with nimbleness and talent for setting and achieving a forward-thinking direction for an organisation are all required attributes. 

  • A demonstrated record of accomplishment in creating and implementing sustained growth strategies in a non-profit or corporate environment; fundraising experience is a definite asset.

  • Demonstrated ability to effectively lead, motivate and develop staff; must be self-motivated and responsible; able to work independently with minimal supervision.

  • Proficiency in computer applications software, including Microsoft Office (Word, Excel, Access, and PowerPoint) and Microsoft Teams. 

  • A driver’s license is required.

Package

  • Salary $6,000 - $7,000 per month plus benefits 

Deadline

  • 21 November 2025

How to apply

APPLY FOR JOB