Director Performance Strategy Jobs in Ontario (NOW HIRING)

At Glassroom, we transform brilliant strategies into inspiring results.

Glassroom is a fast-growing independent media agency, a true laboratory where we prioritize transparency with our advertisers, the continuous professional development of our experts, and the constant improvement of our practices.
We are convinced of the strength of the collective. It's curious, ambitious, and autonomous humans who allow us to offer a unique service to our clients. Human intelligence and teamwork are the fuel of our agency.

We are part of Humanise, a collective of independent and complementary companies that share a simple conviction: consumers are first and foremost people.

At Glassroom, we don’t just accept differences—we celebrate them. We believe that a diverse team brings a wider range of perspectives, leading to more innovative solutions and a better environment for everyone. We are committed to building a space where every "you" feels welcome, regardless of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.
Even if you don’t check every single box on this job description, we encourage you to apply. We value potential, passion, and lived experience just as much as a formal checklist.

Job description

As a Director, Strategic Planning, you will be responsible for the day-to-day strategic leadership of client accounts (retail), delivering best-in-class, omnichannel media solutions. You will champion clear, impactful media strategies and serve as a trusted partner to your clients, internal teams, and vendor partners. This role requires a collaborative leader who can mentor direct reports, partner with agency management, and develop and support dynamic plans that deliver measurable business results.

Your responsibilities (What You Will Do Daily)

• Strategic Media Leadership: Guide the development and execution of integrated media strategies and actively lead client planning sessions and key deliverables.

• Subject Matter Expertise: Serve as an agency SME on core planning principles, emerging channels, and market trends. You must be able to think strategically about platforms and media of all types. You can also follow our proprietary media planning approach, Clearframe.

• Client Advocacy & Presentation: Formulate clear, data-informed rationale for media recommendations and present compelling strategies directly to clients.

• Performance Optimization: Monitor campaign performance alongside cross-functional teams, leveraging key metrics to refine strategies and maximize impact.

• Operational & Team Leadership: Oversee the planning and implementation process across Supervisors, Planners, and Campaign Managers , mentoring direct reports and managing day-to-day media operations. Collaborate with leadership on the account across multiple markets.

• Innovation: Stay ahead of industry shifts and foster a culture of creative, forward-thinking media planning. Be able to leverage analytics reports to adjust plans. And be able to identify areas of growth for new projects for clients and business development.

• Relationship Management: Build trusting, collaborative partnerships with clients at all levels, proactively managing business concerns to solve issues early.

Your assets (What you bring)

• Experience: 8–10+ years in media planning, buying, or strategic marketing (agency experience preferred).

• Omnichannel Expertise: Proven track record planning across all media channels (digital, broadcast, OOH, print, audio).

• Client & Communication Skills: Confident in client-facing environments with exceptional written, verbal, and presentation skills.

• Empathetic communicator: Listens well and responds with care to team members.

• Active listener: Values different viewpoints and seeks to understand before being understood.

• Relationship builder: Connects easily and builds trust across diverse groups.

• Leadership & Collaboration: Strong attention to detail with a natural ability to mentor talent, influence stakeholders, and work cross-functionally.

• Technical Skills: Advanced proficiency in Microsoft Office (Excel, PowerPoint, Word) and standard media planning software.

• Education: Post-secondary education in marketing, business, or a related field is an asset.

Your skills (Your Glassroom Mindset)

• Leadership and strong communication skills; you enjoy working in a team. You are starting to master and implement change management in an organization.

• Curious; you like to ask questions to understand current ways of doing things.

• Rigorous; you treat client budgets with diligence and strong attention to detail.

• People Over Process: You know how to build an effective process, but you also factor in how people adopt it and how it aligns with the requirements of financial rigour.

What Glassroom Offers You (Our Benefits)

At Glassroom, we invest in your well-being and development:

• Hybrid Work: A perfect balance with 3 days in the office for team connection and 2 days remote.

• Generous time off: 3 weeks of annual vacation + the agency is closed during the Holiday season.

• "Human" days: All statutory holidays doubled + 5 human days to take care of yourself + 1 volunteer day to give back to the community.

• Comprehensive health: Group insurance plan (life, medication, dental, paramedical, travel...) with 3 coverage options.

• Active well-being: $250 per year reimbursed for your physical activities or the purchase of home fitness equipment.

• Green transportation: Discounts on Bike share

Ready to transform ideas into business success with us? We look forward to hearing from you! #glassroom