Director of Operations - Real Estate Management Job at Summit Search Group, Blue Mountains, ON

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  • Summit Search Group
  • Blue Mountains, ON

Job Description

About Our Client: Our client is a dynamic and growing, founder-led Canadian business group with a diversified portfolio spanning aviation, hospitality, real estate, retail, luxury charter, and craft brewing.

Position Scope: The Director, Operations is responsible for overseeing the performance, structure, and integration of business units across a diverse group of companies. The individual will ensure that each company has the right leadership, clear operational procedures, efficient reporting lines, and aligned goals. They seek someone who is highly structured, systems-oriented, and excellent at executing playbooks, holding teams accountable, and translating strategy into real-world results. Serving as the day-to-day integrator and executor across a diverse group of companies, this person thrives in the weeds, builds processes others can follow, and keeps multiple businesses operating smoothly without needing to reinvent the wheel.

Responsibilities:

  • Provide day-to-day leadership across all business units including Aviation, Hospitality, Real Estate, Retail, Brewery, and Luxury Charter.
  • Ensure each company is held accountable to KPIs, budgets, and standard operating procedures.
  • Act as the liaison for all site-level managers, including General Managers and Operational Leads.
  • Implement, standardize, and enforce SOPs, workflows, and operational cadence (e.g. weekly calls, monthly performance reviews).
  • Ensure existing software systems and reporting tools are effectively utilized and optimize where necessary.
  • Maintain rigorous performance tracking and monthly reporting in collaboration with functional leaders.
  • Evaluate and mentor business unit leaders, instilling a culture of accountability and clarity in role expectations.
  • Work with the Director of Human Resources to define roles, manage performance issues, and support leadership development.
  • Encourage confident leadership through mentoring, not micromanagement.
  • Interface with Directors of Finance, HR, and Technology to align business unit activities and share best practices.
  • Ensure all compliance, and regulatory frameworks are met with appropriate internal and external resources.
  • Maintain tight collaboration with the Director of Technology and Director of HR to optimize tools, culture, and service delivery.
  • Drive margin, efficiency, and quality enhancements across all lines of business.
  • Identify and replicate high-performing practices between divisions.
  • Lead change management initiatives and performance turnarounds where necessary.

Required Skills and Knowledge:

  • Confident, direct communicator with high emotional intelligence and self-awareness.
  • Calm under pressure; proactive and accountable leader.
  • Inspires confidence and fosters leadership development by mentoring and empowering team members to take on greater responsibilities and grow within the organization.
  • Strategic executor who thrives in complexity and brings clarity through structure.
  • Proven ability to oversee and lead diverse teams across industries such as manufacturing, distribution, retail, or service-based businesses.
  • Experience in environments with seasonality, dynamic schedules, and unconventional operating hours.

Education and Experience:

  • Bachelor’s degree in Business Administration, Operations Management, or related field preferred.
  • 8+ years of experience in operations leadership roles, ideally across multi-site or multi-industry environments.

Summit Search Group is a fair and equitable search firm. We welcome and encourage applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the recruitment and selection process.

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