Sr. Director, Strategy & Foresight

DEADLINE TO APPLY: WEDNESDAY, NOVEMBER 18TH, 2026

The Greater is looking for a Sr. Director, Strategy & Foresight to join our team.

This is a senior strategy role for someone who understands how organizations use brand, sponsorships and other strategic partnerships to drive their business. You’ll work across a range of client projects, helping organizations make better decisions, identify opportunities, solve complex problems and bring new thinking to the table.

Sponsorship and partnerships are an important part of our work, but this role will also contribute across broader business and brand strategy projects.

We’re looking for someone who can do the work, not just manage it. You should be equally comfortable conducting a landscape scan, writing an executive brief, facilitating a workshop, analyzing data or sitting across from a senior client and delivering a clear recommendation.

Most importantly, we’re looking for someone who is proactive. Someone who sees something interesting and brings it forward. Who has a point of view. Who doesn’t wait for a perfectly defined brief, but can mobilize quickly to turn an observation or opportunity into a recommendation.

What you'll do:

Your work will include:

• Leading and contributing to strategy development across business, brand, sponsorship and partnership challenges.
• Conducting landscape scans, research and competitive analysis to identify trends, opportunities and implications for clients.
• Turning data, research and cultural signals into clear insights, recommendations and strategic stories.
• Developing executive communications, strategic presentations, briefs and recommendations for senior audiences.
• Designing and facilitating working sessions, ideation sessions and senior-client discussions.
• Bringing proactive ideas and perspectives to clients, not just responding to briefs.
• Working across client and agency teams, navigating different disciplines, organizations and perspectives while keeping the work moving.
• Helping clients consider how changing consumer behaviour, technology, culture and business models could affect their organizations and strategies.
• Applying strategic foresight, trends analysis and scenario thinking to identify what may be coming and what it could mean for clients.

What we're looking for:

You have meaningful experience in strategy, brand, sponsorship, partnerships or a closely related field, and you’re comfortable operating at a senior level.

You can move between big-picture thinking and hands-on delivery. You know how to take in a lot of information, find what matters and make it simple. You’re confident enough to have a point of view and collaborative enough to work within a larger team.

Specifically, we're looking for someone who:

• Has strong strategy experience, with meaningful experience in sponsorship, partnerships or brand strategy.
• Has experience or strong working knowledge of financial services and banking. Experience in payments, fintech, neobanks and/or loyalty programs is also valuable.
• Is tapped into sport, entertainment and culture and genuinely curious about what's changing.
• Has experience working with senior clients and is polished and credible in executive settings.
• Can navigate complex, multi-agency and inter-agency teams.
• Is a strong writer and communicator who can make complicated ideas clear.
• Is comfortable with numbers, data and analysis — and knows how to turn them into a story and recommendation.
• Is proactive and self-directed. You bring forward insights, recommendations and ideas rather than waiting to be asked.
• Understands traditional sponsorship models but isn't beholden to them. We're looking for someone interested in new approaches, new business models and new ways sponsorship can create value.
• Can facilitate a workshop and help groups make decisions.
• Has experience with strategic foresight, trends analysis, scenario planning or related methodologies. This is an asset, not a requirement.
• Experience or strong working knowledge across arts and entertainment and/or Latin America would also be an asset. If you have relevant experience in these areas, we'd like to hear about it.

How we work:

This role reports to the Partner & Head of Strategy at The Greater and works closely with colleagues across the firm, as well as with clients and agency partners.

This is not a remote role. You should expect to work in person three to four days per week across The Greater, client and other locations in the GTA. Some travel will also be part of the role. Occasional evening and weekend availability will be needed for client events and other work-related commitments.

Compensation:

The expected salary range for this role is $140,000–$155,000, depending on experience.

Interview process:

Our interview process will involve multiple conversations and is designed to give us a sense of both your experience and how you think.

Candidates should be prepared for:.

• Scenario-based and case-style questions based on the types of strategic challenges you would encounter in the role.
• A potential conversation with members of a client team and/or interagency partners.

Please note: In effort to ensure a fair hiring process, we will not be taking any meetings with prospective candidates ahead of time to discuss the role. If you're selected, you'll have lots of time to learn more about the role through the interview process.

How to apply:

DEADLINE TO APPLY: WEDNESDAY, NOVEMBER 18TH, 2026

Send the following to [email protected] with the subject line “Sr. Director, Strategy & Foresight”

• Link to you LinkedIn profile.
• A short note — 500 words or less — explaining what makes you a strong fit for this role.
• One prediction for the future of sponsorship or partnerships. Tell us what you think is coming and why it matters.
• Note: applying through LinkedIn is insufficient and you most follow these instructions to be considered for the role.

About The Greater:

The Greater is a strategy consulting firm and social enterprise with a deep specialization in sport and entertainment. We help organizations win the right way — finding clarity in complexity across business, brand and partnership strategy.

We are strategists first, combining senior-level counsel and hands-on delivery with deep sector expertise and a connected network across the Canadian sport and entertainment industry.

Founded on the belief that business can be great and do good, The Greater reinvests 50% of its net profit back into community organizations — an industry-leading commitment that has driven more than $400,000 in community investment to date.