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Executive Leadership jobs in Winnipeg, MB

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    • 3+ years supporting founders, executives, or entrepreneurs.
    • Executive assistant or high-level administrative: 4 years (required).
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Job Post Details

Executive Assistant - job post

The Boss Life
Winnipeg, MB
$70,000–$90,000 a year - Full-time

Job details

Pay

  • $70,000–$90,000 a year

Job type

  • Full-time

Location

Winnipeg, MB

Benefits

Pulled from the full job description

  • Mileage reimbursement
  • Vision care
  • Dental care
  • Extended health care
  • Wellness program
  • Company events
  • On-site parking

Full job description

Who We Are

The Boss Life is a portfolio of fast-growing companies including Captivation Hub, Online Profit Secrets, and The Boss Life Masterminds. We build AI-native software, support entrepreneurs, and operate in a fast-moving environment focused on execution, growth, and impact.

We are faith-centered, family-first, and committed to excellence. We move quickly, solve problems decisively, and place a high value on integrity, communication, and trust.

What You'll Earn

  • $70,000 to $90,000 CAD base salary
  • Performance bonuses

Benefits:

  • Health, and dental benefits
  • Phone, laptop, and mileage covered
  • Direct access to leadership
  • Growth opportunities into higher-level operational roles

Who We're Looking For

You will excel in this role if you are:

  • Exceptionally organized
  • Composed under pressure
  • Highly dependable
  • Resourceful and proactive
  • A strong communicator
  • Comfortable handling confidential information
  • Able to anticipate needs before they are expressed
  • Comfortable supporting both business and personal operations

You should also:

  • Be comfortable with technology and AI tools
  • Have reliable transportation
  • Be based in or near Winnipeg
  • Be comfortable in a fast-paced entrepreneurial environment

Preferred:

  • 3+ years supporting founders, executives, or entrepreneurs
  • Executive Assistant, Personal Assistant, or Chief of Staff experience
  • Experience coordinating travel and logistics
  • Strong communication and hospitality skills

About the Role

This is not a traditional Executive Assistant position. This is a right-hand operator role supporting the founder across business, family, travel, logistics, communication, and daily operations.

Your mandate is to create order, reduce friction, and protect focus.

You will manage calendars and scheduling, inbox communication, travel and logistics, vendor coordination, family and household support, client hospitality, social media inboxes, and daily operational tasks.

You will be trusted to identify and resolve issues before they escalate.

What Success Looks Like

  • Leaders remain focused on high-value priorities
  • Communication stays clear and well managed
  • Clients receive a high standard of care
  • Critical details are consistently executed without oversight gaps

This is a high-trust, high-ownership role with significant growth potential.

Why Work With Us

You will work closely with accomplished entrepreneurs building companies in AI, software, SaaS, and business education. This is not a traditional corporate environment. It is fast-paced, high-trust, and growth-oriented.

You will gain meaningful ownership, exposure to AI innovation, leadership development, high-level operational experience, and direct visibility into scaling companies and high-performing operators.

If you are the kind of professional who notices what others miss, remains composed under pressure, and brings structure to fast-moving environments, we encourage you to apply.

Pay: $70,000.00-$90,000.00 per year

Benefits:

  • Company events
  • Dental care
  • Extended health care
  • Mileage reimbursement
  • On-site parking
  • Vision care
  • Wellness program

Application question(s):

  • Have you managed calendars, scheduling, or travel coordination before?
  • Tell me a time where you were expected to communicate professionally with clients, vendors, and executives?
  • Tell me your comfort and experience level with technology:

Experience:

  • executive assistant or high-level administrative: 4 years (required)

Location:

  • Winnipeg, MB (required)

Willingness to travel:

  • 25% (preferred)

Work Location: In person

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