Position Type: One-Year Contract

Hours: 35 hours per week, Monday - Friday

Salary: $90,000 annually

Work Location: In person / Toronto, ON

Contract Duration: 1 year (starting early/mid November 2025)

About Jessie’s – The June Callwood Centre for Young Women

Jessie’s is a multi-service resource centre for pregnant young women, young parents, and their children. We offer a broad spectrum of services addressing the social determinants of health and supporting young families as they navigate education, housing, healthcare, parenting, and community life.

We operate from a feminist, pro-choice lens that affirms a person's right to make informed decisions about their sexual health and pregnancy options. Jessie’s is committed to fostering a culture of diversity, equity, inclusion, and belonging (DEIB) in all aspects of our work—with both staff and participants.

Jessie’s serves a diverse population of young women and families - many of whom are navigating multiple systemic barriers, including poverty and racism. Services are delivered by a multidisciplinary team, including social workers, early childhood educators, healthcare professionals, and child and youth workers, through both structured programming and a drop-in setting.

Key Responsibilities

1. Program Leadership & Management

•Lead the design, delivery, and evaluation of participant-centered programs for young women, young parents, and their children.

•Supervise and support a multidisciplinary team working in both structured and drop-in program settings.

•Chair bi-weekly service coordination meetings with the direct service team to ensure alignment and collaboration across programs

•Develop and apply program evaluation tools; track data and recommend changes to improve service delivery.

•Prepare required reports for funders and internal use (as required).

•Monitor program budgets and approve expenditures in line with organizational priorities.

2. Human Resources (in collaboration with the Executive Director)

•Lead the recruitment, hiring, training, coaching, and performance management ofprogram staff.

•Build team capacity through supervision, mentorship, and team-building.

•Address and support resolution of staff and participant-related concerns.

3. Financial & Funding Support:

•Assist in the preparation and submission of funding proposals and reports for government and community funders (e.g., United Way).

•Monitor program financials to ensure alignment with approved budgets.

4. Facilities & Operations (as required)

•Support oversight of building maintenance, IT systems, and vendor contracts, in theabsence of the Executive Director.

5. External Relations & Partnerships:

•Maintain Jessie’s social media platforms and ensure regular communication updates.

•Plan and coordinate six outreach events per year in collaboration with program staffand community partners.

•Oversee the development and distribution of Jessie’s newsletter, ensuringconsistent, engaging, and timely communication with stakeholders.

•Act as liaison with the Toronto District School Board for Jessie’s Section 23/ECPPschool program.

6. Board & Committee Support:

•Prepare reports and materials for Board Committees as requested.

•Attend Committee meetings as required.

Qualifications & Experience:

•Minimum 3 years of experience managing multidisciplinary teams in a community or drop-in setting.

•Strong background in program development, staff supervision, and service delivery for young women and families facing complex social and economic challenges.

•Ability to think strategically and contribute to organizational and program planning.

•Demonstrated understanding of the unique challenges faced by pregnant and parenting youth.

•Proven ability to lead with an equity-focused approach that aligns with Jessie’s feminist,pro-choice lens and commitment to diversity, equity, inclusion, and belonging (DEIB).

•Excellent interpersonal, organizational, and conflict resolution skills.

•Skilled in managing conflict, crises, and escalating situations calmly and confidently.

•Skilled in using data, feedback, and evaluation tools to guide program improvements and decision-making.

•Experience developing and maintaining respectful, collaborative, and productive relationships with partners, and external stakeholders.

•Experience with program budgeting, grant writing, and outcome evaluation is an asset.

How to apply: Please submit your resume and cover letter (in a single PDF) to joanna@jessiescentre.org by September 22, 2025. Applications will be reviewed as they are received, so early submission is strongly encouraged.

Jessie's Centre is committed to the principles of employment equity. We strongly encourage applications from women of diverse race and culture groups, Indigenous women, women with ‘dis’abilities, and 2SLGBTQ+ community.

We thank all applicants for their interest, however only those selected for an interview will be contacted.