Strategy Director at 123Dentist – Toronto, Ontario
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About This Position
Reports To: Chief of Staff to the CEO
Location: Toronto (4 days Onsite, 1 Day Remote)
Employment Type: Permanent Full-Time
Job Overview:
We are seeking a Senior Director, Strategy and Planning to join the Office of the CEO, reporting to the Chief of Staff. This role is the strategic engine of the Office of the CEO, responsible for driving the execution of priorities across the enterprise, managing cross-functional projects from early scoping through to delivery, and ensuring the company has the analytical and strategic horsepower to move fast on the things that matter most.
The Senior Director leads the Enterprise Strategy and Transformation function while also acting as a direct extension of the Chief of Staff on cross-functional initiatives, board and executive materials, business case development, and planning processes. They work in close partnership with Finance and FP&A, owning the strategy and business plan layer that sits alongside and complements the financial planning work held by Finance.
The ideal candidate brings rigorous strategic thinking, strong project execution instincts, and the credibility and relationship skills to engage senior business leaders with confidence. This is a builder's role. The function is being established, and the Senior Director will be foundational to how it is designed, operates, and scales.
Responsibilities and Duties:
Cross-Functional Project Execution
- Lead and execute strategic initiatives and cross-functional projects on behalf of the Chief of Staff and Office of the CEO, from early scoping and business case development through to implementation and follow-up.
- Manage project plans, stakeholder engagement, and delivery milestones across complex, multi-functional initiatives, ensuring the right people are aligned and progress is sustained.
- Partner with the operating businesses by building rapport with key stakeholders across the 123Dentist network, working with them effectively on project delivery while acting as an advisor on important strategic questions and the annual planning and review cycle.
- Develop senior-level reports, presentations, and decision-support materials to facilitate executive discussions, board sessions, and CEO agenda items.
- Identify and scope new initiative opportunities and business issues, developing the analytical foundation and business cases needed to support senior decision-making.
Strategy and Planning
- Support the Office of the CEO to co-lead the annual and multi-year strategic planning process alongside Finance, owning the strategy and business plan layer above and alongside the financial plan.
- Maintain an enterprise-level view of the initiative portfolio, tracking strategic alignment, sequencing, and progress, and provide senior leadership with a strategy and business plan view of how the portfolio is delivering against the company's direction, alongside the financial picture held by Finance and FP&A.
- Design and implement initiative gating frameworks that bring consistent rigour to how the organization evaluates, sequences, and commits to major investments.
- Build communication and collaboration bridges across functions by sharing best practices, identifying strategic links between initiatives, and driving consistency in how priorities are framed and communicated.
Business Case and Investment Quality
- Partner with ELT functions to strengthen business cases before they reach the CEO or board, ensuring strategic questions are well-framed and assumptions are clearly tested.
- Develop and maintain standardized strategic frameworks and analytical tools for use across the organization.
ELT Partnership and Advisory
- Act as a strategic thought partner and advisor to the Chief of Staff and ELT members, helping them shape, pressure-test, and articulate functional strategies in the context of the enterprise agenda.
- Support the Chief of Staff in managing cross-functional priorities, escalations, and decision-making processes that require a neutral, enterprise-wide perspective
Team and Function Building
- Contribute to the buildout of the ES&T function under the Chief of Staff's leadership, playing a leading role in how it develops and is perceived across the organization.
Education, Credentials, Qualifications:
Experience
- Eight or more years of relevant experience in strategy, ideally at a top-tier consulting firm or in corporate strategy at a leading Canadian organization.
- Three or more years of direct team leadership experience.
- Strong financial and business acumen applied to complex, multi-unit operating businesses. Prior experience in Canadian healthcare, retail, or consumer services is a strong asset.
- Project management abilities to structure work in executable pieces and lead cross-functional teams in a fast-paced environment.
- Experience building or formalizing planning processes and governance infrastructure from an early stage is strongly valued.
- Demonstrated ability to build effective and trusted relationships across complex, matrixed organizations.
Education
- Bachelor's degree or higher in a relevant field such as business, economics, or finance from a top-tier university.
Required Skills & Abilities:
- Excellent communication skills, with the ability to distill complex information into clear messages for senior audiences including the C-suite and board.
- Exceptional structured thinking and analytical capability. You impose clarity on unstructured problems and are energized by environments where the path is not fully defined.
- Sound judgment and discretion. This role operates at the center of the organization with access to sensitive strategic and commercial information.
- A collaborative, low-ego operating style. You are a genuine partner to the businesses and to Finance, not an oversight layer.
- A builder's mindset. You are energized by creating structure where none previously existed.