Strategy Jobs in Pickering, ON (NOW HIRING)

The Strategy Manager is the senior operational layer of Foundation's strategy practice. This role exists to own client relationships at the oversight level, develop the strategists beneath them, and free VP-level leadership to operate on business growth, team architecture, and company direction.

The Strategy Manager is accountable for strategic quality across a $2M+ book of business, acts as the primary escalation point for their assigned accounts, and takes full ownership of the people leadership gap that currently sits between individual strategists and VP-level oversight. They are expected to hold positions, defend recommendations under pressure, and grow the capabilities of their team without waiting to be asked.

• Serve as the senior point of contact for each account in your book, building and maintaining relationships with budget decision-makers and senior client stakeholders.
• Act as the primary escalation owner when strategic direction is challenged, client expectations are at risk, or a situation requires a more senior voice.
• Host strategy presentations, sell the direction, and hold your ground under pushback. Clients should feel they have a senior strategic partner, not just access to a team.
• Maintain a clear, current view of account health across your entire book, surfacing risks to the VP of Strategy before they become problems.

• Oversee GEO and content strategy execution across every account you own, ensuring work is aligned with the defined strategic direction and meeting client-specific KPIs.
• Provide meaningful oversight review on strategic deliverables including content plans, QBRs, and monthly reporting, identifying drift, outdated assumptions, or missed opportunities.
• Bring a GEO-first lens to every account. You should be fluent in generative and answer engine optimization, and it should show in how you review and elevate the work.
• Partner with Account Management on each shared client to ensure contracts, upselling, and cross-team coordination are handled cleanly and strategically.

• Manage 3-5 strategists with real accountability for their development, not just their output. Build meaningful PDPs, run structured 1:1s, and move people along the specialist-to-strategist path.
• Coach strategists on call confidence, client communication, and the ability to own and defend strategic positions. The most common development gap on this team is deference; your job is to close it.
• Score and review strategist client calls using the Foundation performance rubric, delivering specific, actionable feedback that names patterns and sets expectations.
• Develop team GEO capability. Ensure the strategists you lead can articulate and execute generative engine optimization with confidence, not just describe it.
• Flag performance concerns to the VP of Strategy early, with supporting evidence, rather than waiting for a formal review cycle.

• Identify upsell and expansion opportunities within your book and route them to Account Management with a clear strategic rationale.
• Participate in strategic sales conversations for new accounts where your subject matter expertise adds credibility and conversion value.
• Contribute to Foundation's GEO positioning by staying current on platform shifts, citation behavior, and AI-search trends, and by surfacing what matters to the wider team.

• Have moved past legacy SEO and actively build content and GEO strategies for generative and answer engine visibility, not as an add-on but as a core discipline.
• Are fluent in B2B and SaaS/tech client relationships, where the funnel, the stakeholder dynamic, and the sales motion are fundamentally different from B2C.
• Can hold a position under pressure. You present, defend, and close on strategy recommendations in front of senior client stakeholders without defaulting to hedging or deferral.
• Want to build people, not just manage them. You have real examples of growing a direct report's capability, not just a willingness to try it.
• Are ready to lead a team before you feel completely ready. You default to ownership, not escalation.

• 5+ years in digital strategy, content strategy, or multi-channel marketing strategy, with at least 2 years in a senior or oversight capacity.
• Demonstrated experience managing or meaningfully developing at least one direct report.
• Proven GEO fluency: you have built and delivered content strategies designed for AI-driven answer engines and can speak to it with authority.
• Strong B2B or SaaS/tech client portfolio, with experience presenting and defending strategy at the VP or Director level.
• Strong analytical capabilities across digital platforms such as Google Analytics, Search Console, Ahrefs, and HubSpot.
• Exceptional ability to communicate complex strategic direction with precision and confidence, in writing and in real-time client conversation.

1. Account Health and Retention

Target: Zero unmanaged escalations. Post-Strategy NPS of 8 or above (internal and external). Retention rate across your oversight book remains positive.

2. Strategic Quality

Target: Strategic deliverables across your book are delivered on time, clearly structured, and to spec. Oversight review catches drift before client delivery, not after.

3. Team Performance Development

Target: Each direct report has an active PDP reviewed monthly. At least one strategist advances measurably on a named development gap per quarter, as evidenced by rubric scores and call review data.

4. GEO Execution Quality

Target: GEO strategies recommended across your book reflect current platform behavior and best practice. Accounts influenced by GEO-informed strategic pivots show measurable improvement in AI citation visibility within 90-180 days.

5. Revenue Contribution

Target: Commission tied directly to expansion within your oversight book. Upsell opportunities are identified proactively and routed to Account Management with clear strategic rationale, not flagged after the fact.

• Base Pay Range: $80,000 - $110,000 CAD / year
• Expected Total Comp (OTE): $105,000 - $145,000 CAD+ / year
• How We Set Comp: Final compensation is determined by experience, role level, and location. We use a role level location framework. We pay intentionally, hire globally, and reward impact.

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2. Apply through the application form