Director of Finance & Integrator – Executive Alignment Role

SimplySmart Child Care Centre & Montessori; Oakville; On-site; CAD 180,000 - 228,000; Full time

Job summary

SimplySmart Child Care Centre & Montessori is seeking a Director of Finance & Integrator to support the CEO's vision. This role combines financial strategy and operational leadership, requiring experience in finance and proven leadership skills. The ideal candidate will thrive in a fast-paced, purpose-driven environment and contribute significantly to both the financial and operational successes of the company. Opportunities for growth into executive leadership roles are available.

Benefits

Competitive salary and performance-based bonuses

Flexible schedule

Opportunity for growth into Chief of Staff or Executive Leadership

Work alongside a visionary CEO

Qualifications

• 5+ years in finance or strategic leadership, ideally in wellness or education.
• Proven experience with financial tools and team management.
• A systems mindset and process-oriented approach.

Responsibilities

• Oversee multi-entity financial operations and monitor financial performance.
• Bridge communication between various teams and optimize internal systems.
• Support HR with hiring strategies and anticipate operational bottlenecks.

Skills

Strategic leadership

Financial management

Executive communication

Cross-functional team leadership

Emotional intelligence

Education

Bachelor's Degree in Finance or related field

Tools

QuickBooks

Excel

Job description

Director of Finance & Integrator – Executive Alignment Role

Director of Finance & Integrator – Executive Alignment Role

Direct message the job poster from SimplySmart Child Care Centre & Montessori

About Us :

At SimplySmart and OsteoStrong Ontario, we’re more than just businesses—we’re movements. One empowers children through inspired Montessori education. The other transforms adult wellness through cutting-edge

skeletal strength and biohacking technologies. Behind it all is a growing entrepreneurial ecosystem powered by purpose, precision, and people.

As our CEO expands her vision, we’re hiring a Director of Finance & Chief Integrator—someone who can be her right hand, second brain, and calm command center. This role goes far beyond spreadsheets. It’s about making mission-aligned decisions, leading cross-functional teams, and holding the operational reins with clarity and

conviction.

This is your role if you’re the kind of person who says :

Let me take that off your plate.”

Here’s how we streamline that.”

I’ve already handled it.”

Your Impact :

As our Director of Finance & Operations (Integrator), you will :

• Lead Financial Strategy : Manage cash flow, budgets, grants, vendor payments, P&Ls, and quarterly reports across all ventures
• Operational Oversight : Own day-to-day business flow—from construction timelines to franchising deliverables, licensing prep to SOP optimization
• Strategic Execution : Work directly with the CEO to convert vision into reality, providing accountability, prioritization, and decision-making support
• Cross-Functional Leadership : Bridge communication between site managers, finance, legal, franchising, construction, and marketing
• System Optimization : Refine internal systems, workflows, and team accountability to support scalable growth
• Embody the Integrator Role : Act on behalf of the founder with maturity, integrity, and grounded leadership

Key Responsibilities :

• Oversee multi-entity financial operations, including SimplySmart and OsteoStrong locations
• Monitor and report on financial performance, including budgets, KPIs, forecasts, and cash flow
• Supervise and improve internal systems, SOPs, and team accountability frameworks
• Coordinate with legal, construction, and franchising teams on project milestones and compliance
• Manage grant applications, reporting, and government funding processes
• Support HR with hiring strategies, performance reviews, and compensation planning
• Anticipate bottlenecks, align resources, and drive execution across projects

You’ll Thrive In This Role If You Have :

• 5+ years in finance, or strategic leadership (bonus if in wellness, education, or franchise environments)
• Mastery of financial tools like QuickBooks, Excel, and cloud-based systems
• Experience making autonomous decisions, managing budgets, and leading cross-functional teams
• High emotional intelligence, grounded presence, and grace under pressure
• A systems mindset and process-oriented leadership style
• Strong executive communication skills—with a bias for action
• Occasional travel to SimplySmart or OsteoStrong locations in Ontario

What We Offer :

• A rare opportunity to work side-by-side with a visionary CEO
• A fast-paced, purpose-driven environment with real community impact
• Competitive salary and performance-based bonuses
• Potential to grow into Chief of Staff or Executive Leadership
• Flexible schedule within a structured leadership role
• A team that gets it—and gets things done

To Apply :

Send your resume and a 1-2 minute short video explaining why you’re the Integrator Harleen’s been looking for to the email on this job posting.

Seniority level

Seniority level

Director

Employment type

Employment type

Full-time

Job function

Job function

Finance and Sales

Education Administration Programs

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