Director of Planning & Design at The Bentway

Position Title: Director of Planning & Design Reports To: CEO Location: Toronto, ON (Hybrid) Status: Full-time, Permanent Salary: $100,000 – 110,000 Deadline to Apply: Monday, February 2 at 5pm Position Summary The Director of Planning and Design leads The Bentway’s planning, design, and public realm initiatives, shaping the organization’s strategic growth along the Gardiner Expressway corridor and across all Bentway sites. This role oversees the Planning and Design department, directing the development and implementation of long-term framework planning, large-scale capital projects, public space enhancements, pilot programs, and community engagement strategies. The Director will set multi-year departmental objectives for projects and initiatives, ensuring strategic growth of the Bentway is coordinated across other internal divisions, is aligned with the objectives of stakeholders, and is supported by the Bentway’s leadership team. In addition, the Director will support capital campaign planning, sectoral network development, and revenue-generating initiatives to sustain and expand Planning and Design activities. This includes offering project insights, developing design concepts, and providing strategic guidance to secure funding, foster collaborations, and build organizational capacity. As a key member of the senior team, the Director also advances organizational priorities and ensures The Bentway remains a leading site for public-space innovation and civic imagination.
This is a hybrid role consisting of 2 days in office and 3 days work from home. Additional days in office/on-site may be required. About The Bentway The Bentway is a dynamic civic organization dedicated to enhancing urban life through the design and implementation of innovative public spaces, public programming, and site operations. Deeply rooted in Toronto’s urban fabric, The Bentway leads a creative movement to re-imagine the possibilities of the Gardiner Expressway. We believe in the power of art and culture to spark the urban imagination, transform communities and foster vibrant, inclusive cities. The Bentway Conservancy is a non-profit organization and registered charity that works closely with the City of Toronto, artists & creatives, and local communities to bring our work to life. Responsibilities Strategic Leadership

• Collaborate with the CEO and senior leadership to define the long-term vision and strategic priorities for The Bentway’s Planning and Design department
• Translate organizational goals into actionable strategies for public realm enhancements, capital projects, and urban design initiatives
• Represent The Bentway in municipal, civic, and professional forums, advocating for design excellence, community engagement, and the organization’s mission
• Proactively seek out and identify opportunities for alignment with external agencies and stakeholder projects to bolster the Bentway’s network, financial position, and capacity for impacting large scale change
• Contribute to organization-wide initiatives, including sustainability, accessibility, equity, and brand development

Capital Project Oversight

• Oversee all major capital projects, ensuring alignment with organizational priorities, budgets, timelines, and quality standards
• Report on capital projects as required to the Bentway Board and Board Sub-Committees to maximize effectiveness and minimize risks
• Approve project scopes, budgets, RFPs/RFQs, and contracts; monitor compliance with procurement policies, building codes, and sustainability standards
• Guide project teams in delivering projects from feasibility through construction and occupancy
• Work collaboratively with Bentway Facilities & Production teams to ensure that ongoing planning for capital projects accounts for the needs and practices of daily operations and programming

Public Realm & Urban Design

• Lead the development and implementation of public realm strategies, design guidelines, framework plans, programming initiatives, and visual communications to engage stakeholders and the public
• Apply best practices and champion innovative approaches to public space design that integrate sustainability, accessibility, programming, and multi-use functionality
• Integrate planning, design, and programming initiatives to enhance urban experience and community engagement
• Ensure that projects are supported through with succinct, brand-forward communications and visuals that build consensus in the Bentway’s vision across private and public sectors

Capital Campaign & Fundraising Support

• Partner with the CEO and development teams to support and inform capital campaigns and fundraising initiatives
• Working with the Senior Manager, develop feasibility studies, cost estimates, renderings, and design concepts to support campaign materials, donor presentations, and investment proposals
• Participate in donor briefings, site tours, and presentations to advance funding goals for strategic growth projects
• Identify and steward planning and design-related funding opportunities, including grants, sponsorships, consulting, cost-share programs, and in-kind partnerships

Sectoral Network Development

• Foster partnerships with civic, non-profit, and private sector organizations to strengthen The Bentway’s influence in urban design, public realm, and cultural sectors
• Develop and maintain sectoral networks, including the Gardiner Corridor Alliance, to facilitate knowledge sharing, collaboration, and advocacy
• Represent The Bentway in sectoral forums, advisory committees, awards submissions, conferences, publications, advisory boards and professional networks

Departmental Leadership & Management

• Lead, mentor, and evaluate Planning and Design staff, ensuring collaboration, professional growth, and high performance.
• Oversee departmental staffing plans, budgets, resource allocation, and operational planning.
• Promote cross-departmental collaboration to align Planning and Design initiatives with programming, operations, and fundraising strategies
• Establish clear performance metrics, project tracking, and reporting systems for the department.

Stakeholder & Community Engagement

• Cultivate strong relationships with government agencies, community partners, design consultants, contractors, and other key stakeholders
• Provide direction to Senior Manager and staff team on consultations and public engagement processes to ensure projects reflect community needs, priorities, and equity considerations.

Other Responsibilities

• Perform additional duties as assigned, including supporting special projects, partnerships, pilot initiatives, and organizational growth strategies

Qualifications

• Professional degree in architecture, landscape architecture, urban planning/design, construction management, or a closely related field, with a minimum of 8–10 years of professional experience in similar or a related discipline.
• Demonstrated leadership experience overseeing complex capital and public realm projects from feasibility and site planning through design stages, construction, and occupancy, with accountability for budgets, schedules, quality, and risk management
• Strong design leadership, with a portfolio demonstrating design excellence and the ability to steward a clear design vision across multiple projects and collaborators
• Proven ability to work collaboratively across sectors and disciplines, including municipal and other government agencies, private-sector partners, consultants, cultural institutions, funders, professional organizations, and community stakeholders
• Deep understanding of public-realm planning and urban design best practices, including sustainability standards and codes, climate resilience, universal design, accessibility, equity, multi-use programming, and operations-informed design
• Evidenced track record of running meaningful engagement with local residents, equity-deserving groups, business improvement areas (BIAs/BIDs) and city partners
• Demonstrated experience supporting capital campaigns and fundraising initiatives through feasibility studies, cost estimates, design concepts, visual materials, and donor-facing presentations
• Experience leading and managing teams, including staff supervision, mentoring, performance evaluation, resource planning, and departmental budgeting
• Demonstrated capacity to manage multiple projects simultaneously while maintaining quality and consistency
• Exceptional communication and presentation skills, including the ability to represent the organization publicly in meetings, design reviews, and professional forums, translating complex planning and design concepts into clear, compelling materials for diverse audiences.
• Working knowledge of visual communication and design tools; including Computer-Aided Design (CAD) and Building Information Modeling (BIM) software; Adobe Creative Suite . Working knowledge of rendering software is considered an asset

Applications The Bentway is committed to fostering a positive and supportive environment that promotes equity and diversity. We encourage applications from equity deserving groups, including Indigenous, Black and racialized applicants, persons with disabilities, and women. In accordance with the Ontario Human Rights Code, Accessibility for Ontarians with Disabilities Act, 2005, accommodation will be provided at any point throughout the hiring process, provided the candidate makes their accommodation needs known to The Bentway Conservancy at [email protected]. We kindly ask that no phone calls or emails are made to staff members. All questions regarding the position must be sent to [email protected]. To Apply Apply with a resume and cover letter via The Bentway’s job board: https://thebentway.applytojobs.ca/ Deadline to Apply: Monday, February 2 at 5pm Application Components:

• Resume (PDF format, no more than three pages)
• Cover Letter (PDF format, no more than three pages)
• Portfolio consisting of three recent projects.

The Bentway does not use AI to sort candidates, each application will be reviewed by a person. We thank all applicants for their interest and will endeavour to contact all applicants, whether successful or not.