Director of Planning & Design

The Bentway Conservancy; Toronto; On-site; CAD 100,000 - 110,000; Full time

Job summary

A leading civic organization in Toronto seeks a Director of Planning & Design. This role will lead strategic planning and design initiatives, oversee capital projects, and enhance community engagement. The ideal candidate has extensive experience in urban design and management of complex projects, alongside a dedication to promoting inclusive public spaces. This full-time position offers a salary range of $100,000 – $110,000 annually and supports hybrid work arrangements.

Qualifications

• Minimum of 8-10 years of professional experience in related fields.
• Experience managing public realm projects from planning through to occupancy.
• Evidence of successful fundraising and capital campaigns.

Responsibilities

• Define vision and strategic priorities for the Planning & Design department.
• Oversee major capital projects ensuring alignment with priorities and budgets.
• Lead public realm strategies and design guidelines integration.

Skills

Leadership

Urban design knowledge

Stakeholder engagement

Project management

Communication skills

Education

Professional degree in architecture, landscape architecture, or urban planning

Tools

CAD software

BIM software

Job description

Position Title

Director of Planning & Design

Reports To

CEO

Location

Toronto, ON (Hybrid – 2 days in office, 3 days remote; additional on‑site days may be required)

Salary

$100,000 – $110,000 per year

Employment Type

Full time, Permanent

Deadline to Apply

Monday, February 2 at 5pm

Position Summary

The Director of Planning & 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. The role oversees the Planning and Design department, directing 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, ensure strategic growth is coordinated across internal divisions, align with stakeholder objectives, and support the Bentway’s leadership team.

In addition, the Director supports 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, securing funding, fostering collaborations, and building organizational capacity. As a key member of the senior team, the Director advances organizational priorities and ensures The Bentway remains a leading site for public‑space innovation and civic imagination.

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. 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 registered charity that works closely with the City of Toronto, artists and creatives, and local communities.

Responsibilities

• Strategic Leadership
  • Collaborate with the CEO and senior leadership to define vision and strategic priorities for the 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.
  • Seek opportunities for alignment with external agencies and stakeholder projects to strengthen the network and financial position.
  • Contribute to organization‑wide initiatives, including sustainability, accessibility, equity, and brand development.
• Capital Project Oversight
  • Oversee all major capital projects, ensuring alignment with priorities, budgets, timelines, and quality standards.
  • Report on projects to the Board and sub‑committees, maximizing effectiveness and minimizing risks.
  • Approve scopes, budgets, RFPs/RFQs, and contracts; monitor compliance with procurement policies, building codes, and sustainability standards.
  • Guide project teams through feasibility, construction, and occupancy stages.
  • Coordinate with Facilities & Production teams to incorporate operational needs into planning.
• Public Realm & Urban Design
  • Lead development and implementation of public realm strategies, design guidelines, framework plans, programming initiatives, and visual communications.
  • Apply best practices and champion innovative approaches that integrate sustainability, accessibility, programming, and multi‑use functionality.
  • Integrate planning, design, and programming to enhance the urban experience and community engagement.
  • Produce brand‑forward communications and visuals that build consensus across private and public sectors.
  • Partner with the CEO and development teams to support capital campaigns and fundraising.
  • Collaborate with the Senior Manager on feasibility studies, cost estimates, renderings, and design concepts for donor presentations.
  • Participate in donor briefings, site tours, and presentations to advance funding goals.
  • Identify and steward 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 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, and professional networks.
  • Lead, mentor, and evaluate staff, ensuring collaboration, professional growth, and high performance.
  • Oversee staffing plans, budgets, resource allocation, and operational planning.
  • Promote cross‑departmental collaboration to align initiatives with programming, operations, and fundraising strategies.
  • Establish performance metrics, project tracking, and reporting systems.
• Stakeholder & Community Engagement
  • Build strong relationships with government agencies, community partners, design consultants, contractors, and key stakeholders.
  • Guide the team on 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.
• Demonstrated leadership experience managing 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 and a portfolio demonstrating excellence and ability to steward a clear design vision across multiple projects and collaborators.
• Proven ability to collaborate across sectors and disciplines, including municipal agencies, private‑sector partners, consultants, cultural institutions, funders, professional organizations, and community stakeholders.
• Deep understanding of public‑realm planning and urban design best practices, sustainability standards, codes, climate resilience, universal design, accessibility, equity, multi‑use programming, and operations‑informed design.
• Evidence of running meaningful engagement with local residents, equity‑deserving groups, and business improvement areas (BIAs/BIDs) and city partners.
• 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 supervision, mentoring, performance evaluation, resource planning, and budgeting.
• Capacity to manage multiple projects simultaneously while maintaining quality and consistency.
• Exceptional communication and presentation skills, including the ability to represent the organization publicly and translate complex planning and design concepts into clear, compelling materials for diverse audiences.
• Working knowledge of visual communication and design tools, including CAD and BIM software; rendering software knowledge is an asset.

Applications

We are committed to fostering a positive and supportive environment that promotes equity and diversity. We encourage applicants from equity‑deserving groups, including Indigenous, Black, racialized, persons with disabilities, and women.

In accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act, 2005, accommodation will be provided at any point throughout the hiring process if the candidate informs The Bentway Conservancy of their needs.

We kindly ask that no phone calls or emails be made to staff members. All questions regarding the position must be sent to the email provided in the posting.

To Apply

Please submit a resume and cover letter via The Bentway’s job board by Monday, February 2 at 5pm. Application components:

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

The Bentway does not use AI to sort candidates; each application will be reviewed by a person.

Thank you for your interest. We will endeavour to contact all applicants, whether successful or not.