Regional Manager of Operations

1 day ago

Regina, Saskatchewan, Canada Wheels for the Wise Full time $52,000 - $152,000 per year

Regional Manager of Operations – Wheels for the Wise Inc.

About Us:

Wheels for the Wise Inc. is a rapidly growing Mental health oriented transportation company specializing in serving veterans and individuals requiring safe, professional transportation to and from medical appointments. As we expand across Ontario and Canada, we are seeking a Regional Manager of Operations of Ontario to lead and scale operations in our Ontario region.

The Role:

We are looking for a dynamic, self-motivated leader who thrives in a fast-paced environment. This is not a standard 9-to-5 role—it requires flexibility, strategic thinking, and strong organizational skills. The right candidate will have entrepreneurial experience, management expertise, and a passion for operational efficiency. Ask yourself, "Am I always ahead of the rest of my counterparts at work?" If you answered Yes to that question, I assure you, this opportunity will be your spot to shine.

What You'll Do:

Lead and manage regional operations across all of Western Canada

Work with current Regional Managers across Canada

Develop and implement strategies to optimize logistics, scheduling, and client experience

Recruit, train, and develop high-performing driver teams

Build relationships with clients, healthcare facilities, and veteran organizations to drive growth

Track key performance indicators (KPIs) and optimize processes using data-driven decision-making

Ensure compliance with company policies, government regulations, and vehicle maintenance schedules

Maintain clear communication with drivers, dispatch, and leadership, ensuring smooth day-to-day operations

Adapt quickly to last-minute scheduling changes, client needs, and market demands

What We're Looking For:

Proven management experience in a fast-growing business or startup environment

Entrepreneurial mindset—ability to take ownership, solve problems, and drive growth

Strong logistical and operational skills, with experience managing schedules and resources

Exceptional communication skills across multiple levels (clients, drivers, dispatch, leadership)

Ability to balance high-level strategy with hands-on, in-the-field problem-solving

Experience using spreadsheets and KPI tracking tools (Excel skills are an asset)

Ability to stay composed under pressure and navigate last-minute priority changes

Why Join Us?

Be part of a rapidly growing company with a meaningful mission

Opportunity to shape the future of operations, possibly in multiple provinces

Work in an entrepreneurial, fast-paced, and supportive environment

If you're ready to take on a leadership role where you can make an impact, we'd love to hear from you

Job Type: Full-time

Pay: From $52,000.00 per year

Application question(s):

  • Are you a Veteran or Retired First-responder?
  • A clean driver's abstract and a valid vulnerable sector check will be required as part of the hiring process. Will you be able to provide these if requested?

Experience:

  • Winter Driving experiance: 10 years (required)
  • Excel: 5 years (required)
  • Microsoft Word: 5 years (required)
  • AI usage: 1 year (preferred)
  • technical proficiency (computers, phone apps, etc.) : 5 years (required)

Willingness to travel:

  • 75% (required)

Work Location: On the road

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