Director of Finance & Integrator – Executive Alignment Role

SimplySmart Child Care Centre & Montessori; Oakville; Hybrid; CAD 100,000 - 130,000; Full time

Job summary

SimplySmart Child Care Centre & Montessori is seeking a Director of Finance & Integrator to enhance operational clarity and strategic execution. The role involves leading financial strategies, overseeing operations, and fostering cross-functional collaboration within a dynamic entrepreneurial ecosystem. Successful candidates will possess strong leadership skills and relevant experience in finance, bringing a proactive and solutions-oriented approach to the mission-driven environment.

Benefits

Competitive salary

Performance-based bonuses

Flexible schedule

Opportunity for growth into executive roles

Qualifications

• 5+ years in finance or strategic leadership, preferably in wellness or education.
• Mastery of financial tools like QuickBooks and Excel.
• Strong executive communication skills with a bias for action.

Responsibilities

• Lead financial strategy, manage budgets, and oversee multi-entity operations.
• Bridge communication across cross-functional teams.
• Refine internal systems and workflows to support growth.

Skills

Financial Analysis

Leadership

Strategic Planning

Communication

Decision Making

Education

CPA or equivalent financial designation

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:

• A CPA or equivalent financial designation

• 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

Work Model:

• Hybrid: 4 days in-person at our Oakville HQ, 1 day remote

• 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

• Industries

  Education Administration Programs

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