A Journey of Leadership and Cultural Legacy
"While I appreciate my work experience and academic and other achievements, the greatest thing I have to offer and bring to York South–Weston as City Councillor is my lived experience. No longer facing some of the barriers and challenges does not mean that I have arrived; it means that I have overcome. This is what I desire for those facing similar challenges in YSW, and at least you know where it's coming from."Sileen
Sileen is a multifaceted leader whose life journey and professional career have been profoundly shaped by her diverse experiences and rich cultural heritage. As the daughter of immigrant parents and a long-time tenant of a co-op, she has navigated the complexities of life as a single mother, sole caregiver, and survivor of numerous personal challenges. These experiences have prepared her to connect authentically with community members and advocate for solutions that address real-world barriers. Her desire to pursue municipal leadership is shaped by her faith, lived experience, and desire to serve her community. She leads from a place of empathy and compassion.
Sileen's personal life has been marked by resilience and determination. She has faced and overcome significant challenges, including homelessness, racial discrimination, domestic violence, and mental illness. As the sole caregiver for her elderly mother, who is and has been battling various cancers over 40 years, Sileen's empathy and compassion have been profoundly shaped by her lived experiences.
With over 25 years of federal experience, Sileen has been a dedicated public servant, civic participation champion, and faith-based leader. Her career has focused on advancing accountability, improving service delivery, and supporting community-centered government operations across Canada. While most of her career was strictly administration of legislation, her work includes community-focused outreach that was very successful, resulting in expansion and sustained federal support to previously underserved regions, including the Yukon, the Northwest Territories, and Indigenous communities.
Throughout her federal career, Sileen has served on several committees and boards, including Employment Equity and Diversity, Health and Safety, and Social Development. As an active member of the Public Service Alliance, she has strengthened her advocacy skills, mediating complex workplace concerns and negotiating fair solutions. These roles have reinforced her commitment to transparent governance and collaborative problem-solving.
In 2012, Sileen received the prestigious Queen Elizabeth II Diamond Jubilee Medal, recognizing her exceptional contributions to community and public service across Canada. She has also received long service awards, affirming the trust placed in her work and the consistency of her performance.
Sileen's role as an elections administrator underscores her commitment to democratic processes. She has served federally as the Assistant Returning Officer for University–Rosedale and the Primary Additional Assistant Returning Officer for Toronto Centre, and provincially as the Election Clerk for High Park–Parkdale. Her detail-driven approach ensures electoral operations are conducted with accuracy and respect for legislative requirements.
Outside of federal public service, Sileen serves as a minister for a congregation located in North York, and as the Child, Youth, and Family Coordinator at the Church of St. Peter and St. Simon. She is also the Area Coordinator of Youth Ministry for the South Archdeaconry, supporting youth leaders and programs across more than 40 parishes spanning from Scarborough to Etobicoke. In these roles, she helps strengthen youth engagement, supports volunteers, clergy, and families, and contributes to parish governance as a member of the Advisory Board for both churches.
A graduate of the University of Toronto's Knox College and Wycliffe College, and of Laurentian University, Sileen's academic achievements are extensive, with three Bachelor's degrees, four Master's degrees, and current doctoral candidacy at the University of Toronto. Her involvement in academic governance includes roles such as Chair of the TDSB's SEED Alternative School, board member of the University of Toronto's TST Graduate Students Association, and doctoral member representative on the Graduate Studies Council. Her academic pursuits reinforce her commitment to mentorship and knowledge sharing.
Sileen is a teaching assistant at the University of Toronto, assisting with graduate-level course delivery, which keeps her closely connected to academic inquiry, evidence-based practice, and student learning. The role strengthens her analytical skills, deepens her engagement with emerging scholarship, and reinforces her commitment to mentorship and knowledge-sharing: qualities that complement her broader work in public service and community care.
Sileen is an artist whose work is grounded in a deep appreciation for culture and the richness of artistic expression. Creativity is not only part of her practice: it shapes how she understands communities, identity, and the stories that connect us. She is a five-time national award recipient from the Jamaica Cultural Development Commission. Her creative work demonstrates her lifelong passion for artistic expression and dedication to uplifting the fine arts sector.
Sileen's community work includes founding Sha'Phak, a private women's support group, and partnering with the Canada Revenue Agency's Volunteer Income Tax Program to offer free tax clinics for more than sixteen years. Her leadership style, guided by faith, is grounded in humility and a deep sense of service.
Rooted in service and shaped by resilience, Sileen continues to build pathways that support stronger, safer, and more connected communities. Her leadership prioritizes environmental stewardship and reflects a commitment to care and responsibility.
Municipal government is community work at scale. I am already doing the work. Public office simply expands my reach.
I am running because I want a city where:
- safety and security is prioritized
- support can be felt and seen
- the environment is honoured and protected
- accountability is not optional
- community trust is earned, not assumed
York South–Weston deserves a leader who is a builder of systems, not just a critic of them; a leader who will not simply identify problems, but one who will help design solutions.
Sileen Phillips
