About Transition to Betterness (T2B) Transition to Betterness (T2B) is a Windsor-Essex County–based non-profit organization dedicated to providing comfort to patients and families impacted by life-altering illness. Founded over 30 years ago with the goal of refurbishing two oncology rooms, T2B has grown into a dynamic organization delivering more than 15 ongoing programs, along with numerous capital campaigns across local hospitals. T2B is built on compassion, community, and kindness. Our network of donors, volunteers, and partners plays a vital role in advancing our mission. From pediatric to oncology to palliative care, each of our initiatives is guided by a simple question: What would we do for a family member facing a difficult time? This philosophy continues to inspire meaningful acts of care throughout our community. Position Summary Transition to Betterness is seeking a dynamic and results-driven Director of Operations to support and enhance the organization’s ongoing growth and impact. This role requires an experienced non-profit professional with demonstrated expertise in fundraising, grant writing, operational leadership, and public relations, along with strong connections within the Windsor-Essex community. The Director of Operations will oversee day-to-day organizational functions, support strategic initiatives, and lead fundraising and community engagement efforts. This individual will play a key role in strengthening operational effectiveness, advancing revenue development, and ensuring the organization’s financial sustainability. Salary of $65,000 to $90,000 Key Responsibilities Operational Leadership & Strategy Oversee daily operations, ensuring programs are aligned with T2B’s mission, cost-effective, and delivered to a high standard. Support organizational strategic planning and ensure effective implementation of goals and objectives. Maintain and strengthen the organization’s brand and reputation within the community. Fundraising, Grants & Revenue Development Develop and execute donor-centered fundraising strategies to expand revenue and donor engagement. Lead the planning and execution of fundraising events, sponsorship initiatives, and capital campaigns. Research, write, and manage grant applications, ensuring timely submissions and compliance with reporting requirements. Identify and cultivate new funding opportunities, including foundations, government programs, and corporate partnerships. Develop compelling sponsorship proposals and stewardship strategies for major donors. Financial Oversight & Literacy Support financial planning, budgeting, and forecasting in collaboration with the Board of Directors. Monitor organizational financial performance, ensuring responsible allocation of resources. Interpret financial statements and reports to inform decision-making and organizational strategy. Ensure strong financial practices, accountability, and transparency across all operations. Community & Stakeholder Engagement Serve as an ambassador for T2B, representing the organization in the community and at public events. Build and maintain strong relationships with donors, partners, healthcare stakeholders, vendors, and volunteers. Work closely with the Board of Directors, providing regular updates and leveraging their expertise and networks. Team Leadership Lead, mentor, and support staff and volunteers to achieve organizational goals. Foster a collaborative, inclusive, and high-performing team culture. Leadership Qualities & Skills Confident, compassionate, and collaborative leadership style High ethical standards with a commitment to integrity and confidentiality Strong strategic thinking and decision-making abilities Excellent interpersonal and communication skills Demonstrated grant writing and funding proposal development expertise Solid financial acumen, including budgeting and financial analysis Creative problem-solving and adaptability Flexibility to attend evening and weekend events as required Qualifications 3-5 years of experience in fundraising, marketing, grant writing, or a related field, preferably within the non-profit sector Leadership experience managing teams and stakeholder relationships Demonstrated success in major gift fundraising and corporate partnership development Strong understanding of financial management, budgeting, and reporting Established connections within the Windsor-Essex community considered an asset Ability to serve as a strong public representative of the organization What We Offer Competitive compensation Opportunity to play a key leadership role in a respected and impactful community organization A dedicated and passionate team committed to improving the lives of others Application Process To apply, please submit your resume and a cover letter outlining your qualifications and vision for the role. Applications should demonstrate your understanding of the Windsor-Essex community and your experience in fundraising, grant writing, and public relations. Please send your application by June 30 to with the subject line: Attention Board of Directors .