Director, Strategic Initiatives

About Across Boundaries

Across Boundaries provides equitable, inclusive, and holistic mental health and addiction services and supports for racialized adults and youth aged 16 and older across the Greater Toronto Area. Working within Anti-Racism/Anti-Oppression (AR/AO) and resisting Anti-Black Racism frameworks, our progressive strategies are rooted in current research, meaningful community engagement, and a deep commitment to advancing equity in mental health care.

For more than 30 years, we have worked alongside communities to challenge systemic barriers, advocate for social justice, and improve mental health outcomes for racialized individuals and families.

We are a dedicated team, passionate about the services we provide and the communities we serve. You will thrive at Across Boundaries if you are:

• An experienced practitioner of Anti-Racism, Anti-Oppression, and Anti-Black Racism Frameworks, with a proven ability to embed these principles into programs, policies, practices, and organizational culture through strategy, operations, partnerships, and people leadership.

• An experienced and collaborative leader who enjoys building relationships and bringing people together around a common purpose.

• A strategic thinker who is energized by innovation, organizational growth, and systems change.

• Passionate about creating meaningful impact for the communities we serve.

The Opportunity

Across Boundaries is seeking an experienced, collaborative, and visionary leader to join our leadership team as Director, Strategic Initiatives. Reporting directly to the Executive Director, this position offers an exciting opportunity to help shape the future direction of an organization recognized for its leadership in advancing mental health equity for racialized communities.

As a key member of the Management Team, you will lead organization-wide strategic initiatives that strengthen Across Boundaries' impact, foster meaningful partnerships, and support innovation across the organization. Working at the intersection of strategy and execution, you will translate organizational priorities into actionable initiatives while collaborating with staff, consultants, community organizations, academic institutions, government partners, and sector leaders.

This role is designed to lead and advance strategic initiatives that foster innovation and expand Across Boundaries' impact across the mental health sector. You will identify opportunities, provide strategic oversight of key organizational initiatives, and help ensure strategic priorities are successfully implemented.

Your portfolio will be dynamic and evolving. Current and emerging initiatives include advancing organizational Anti-Racism and Anti-Oppression work, strengthening quality improvement and accreditation initiatives, enhancing organizational data and evaluation, expanding education and training, supporting research and innovation, developing AI-enabled initiatives, building strategic partnerships, and leading new organizational priorities that strengthen our impact across the sector.

This role is ideal for a strategic leader who enjoys building new initiatives, navigating complexity, fostering collaboration across diverse stakeholders, and translating innovative ideas into meaningful organizational impact.

What You Will Do

Reporting to the Executive Director, you will provide strategic leadership across a diverse portfolio of organizational initiatives in the following key areas:

Strategy & Initiative Development

• Lead the development, planning, and implementation of strategic initiatives aligned with Across Boundaries' mission, strategic priorities, and long-term organizational goals.

• Translate organizational priorities into clearly defined initiatives with measurable objectives and outcomes.

• Identify, assess, and advance strategic opportunities that strengthen organizational capacity, innovation, sustainability, partnerships, and community impact.

• Provide strategic advice and recommendations to the Executive Director to support organizational planning, decision-making, and the advancement of strategic priorities.

Initiative Execution & Oversight

• Lead multiple complex strategic initiatives from concept through implementation.

• Provide strategic oversight and coordination of organizational initiatives by working collaboratively with internal staff, consultants, project leads, and external partners to ensure initiatives are effectively planned, implemented, evaluated, and aligned with organizational priorities.

• Establish priorities, timelines, deliverables, and performance measures across concurrent initiatives.

• Provide oversight to organizational consultants and specialized project resources supporting communications, accreditation, evaluation, data analytics, innovation, and other strategic initiatives.

• Monitor initiative outcomes, identify risks and opportunities, and provide recommendations that support continuous improvement and successful implementation.

Organizational Leadership

• Serve as an active member of the Management Team, contributing to organizational planning and decision-making.

• Foster a culture of collaboration, accountability, innovation, and continuous improvement.

• Ensure all work reflects Across Boundaries' commitment to Anti-Racism, Anti-Oppression, resisting Anti-Black Racism, and equity.

• Collaborate across the organization to build alignment, foster engagement, and support the successful integration of strategic initiatives into organizational practice.

Organizational Excellence & Innovation

• Lead initiatives that strengthen organizational quality improvement, evaluation, research, education, communications, innovation, and organizational effectiveness.

• Support projects related to accreditation, data strategy, performance measurement, digital transformation, and emerging AI initiatives.

• Develop sustainable approaches that strengthen organizational learning, collaboration, and continuous improvement.

Partnerships & Systems Engagement

• Build and sustain strategic relationships with community organizations, government partners, academic institutions, healthcare organizations, and advocacy coalitions.

• Represent Across Boundaries at external tables, collaborative initiatives, conferences, and sector engagements.

• Cultivate strategic partnerships that enhance organizational capacity, promote innovation, and advance Across Boundaries' leadership within the mental health and community services sector.

What You Bring

• A graduate degree in Public Policy, Health Administration, Social Work, Education, Public Administration, or another relevant discipline. An equivalent combination of education, lived experience, and professional experience will also be considered.

• Demonstrated experience leading complex strategic initiatives involving multiple stakeholders, organizational change, and cross-functional collaboration within healthcare, community services, mental health, government, education, or related sectors.

• Demonstrated commitment to advancing equity through the application of Anti-Racism, Anti-Oppression, and Anti-Black Racism principles, with a strong understanding of the systemic barriers experienced by racialized communities.

• Experience working at a systems level, including organizational strategy, organizational development, change management, or systems transformation.

• Demonstrated success leading multiple complex, cross-functional initiatives from concept through implementation.

• Exceptional project leadership, organizational, and problem-solving skills, with the ability to manage competing priorities in a dynamic environment.

• Outstanding relationship-building and partnership development skills across diverse stakeholder groups, including community organizations, government, academic institutions, and healthcare partners.

• Excellent communication, facilitation, presentation, and influencing skills.

• A collaborative leadership style that builds trust, empowers others, and fosters strong cross-functional relationships.

• Strong analytical skills with the ability to translate complex information into practical, actionable strategies.

• Experience within the community mental health, healthcare, or broader non-profit sector is preferred.

• Experience leading quality improvement, accreditation, evaluation, or organizational performance initiatives is an asset.

• Experience supporting research, education, policy development, or systems advocacy is an asset.

• Experience leading digital transformation, innovation, or AI-enabled initiatives is an asset.

• Experience working within a unionized environment is an asset.

Why Join Across Boundaries?

Across Boundaries is entering an exciting period of organizational growth, innovation, and strategic evolution. This is an opportunity to play a key leadership role in advancing initiatives that will strengthen the organization, deepen strategic partnerships, and expand our impact across the mental health sector.

As Director, Strategic Initiatives, you will help shape the organization's future by leading transformative initiatives, fostering innovation, and strengthening partnerships that advance equitable mental health care for racialized communities.

You will join a collaborative leadership team that values curiosity, creativity, shared leadership, and meaningful community engagement while supporting work that makes a lasting difference in the lives of the communities we serve.

What We Offer

Across Boundaries offers a competitive total compensation package, including:

• Annual salary of $100,000–$105,000, commensurate with experience and qualifications.

• Comprehensive employer-paid extended health, dental, and vision benefits.

• Twenty (20) vacation days.

• Eighteen (18) paid sick days.

• Five (5) paid personal/wellness days.

• Employee and Family Assistance Program.

• Professional development and continuing education opportunities.

Working Conditions

Across Boundaries is open Monday-Friday 8:00am to 8:00pm and Saturday 10am-6pm. In addition to their regular scheduled work hours/shift, employees also work a rotational schedule consisting of evening and weekend shift(s) every 2 weeks.

How to Apply

Interested applicants are invited to submit a resume and cover letter no later than September 4, 2026, following the application instructions provided with this posting. We thank all applicants for their interest; however, only those selected for an interview will be contacted. An eligibility list may be established for similar positions of various tenures and will be retained for a maximum period of 12 months.

We strongly encourage applications from members of Black and racialized communities and those with diverse backgrounds that may not meet all requirements of our job posting but have equally transferable skills for the role.

Across Boundaries is strongly committed to the principles of anti-racism/anti-oppression and resisting anti-Black racism and adheres to the tenets of the Ontario Human Rights Code. We encourage applications from all racialized communities, ethnic origins, religions, genders, LGBTQ++ abilities.

Our hiring process does not use artificial intelligence (AI) or automated decision making tools in the recruitment or selection process. All applications are reviewed and evaluated by our hiring team.

About Strategisense Consulting

StrategisenseConsulting is a boutique Canadian management consulting firmestablishedin 2000, serving nonprofit, public sector, and purpose-driven organizations. Our services span executive search, organizational strategy and design, leadership development, executive coaching, governance and board effectiveness, and facilitation. Guided by our promise of Purpose. People. Strategy., we partner with mission-driven organizations to strengthen the leadership capacity, organizational systems, and strategic thinking required to deliver lasting impact in the communities they serve.