Part-Time Executive Assistant / Execution Coordinator

5 Hours per Week | Flexible Schedule | Winnipeg / Remote

I’m an entrepreneur involved in commercial financing and several business ventures. I’m looking for a highly organized, proactive person who can help turn ideas into action and keep projects moving forward.

This role goes beyond day-to-day administrative support. I’m looking for someone who enjoys bringing structure to ideas, staying on top of follow-ups, tracking progress, and helping keep priorities moving forward. There will be plenty of variety, and I value someone who is comfortable taking initiative and working collaboratively.

What You'll Do

You’ll work directly with me to:

• Keep track of business ideas, projects and small experiments we're testing
• Turn discussions and ideas into clear next steps
• Maintain a simple project/experiment tracker with deadlines and results
• Follow up with me and others when something is outstanding
• Research vendors, companies, associations, products or opportunities
• Help coordinate meetings, calls and business activities
• Keep important tasks from getting forgotten when priorities change
• Prepare a short weekly summary of what's moving, what's stuck and what needs a decision
• Help determine which experiments should continue, change, scale or stop

Who I'm Looking For

You may be a great fit if you're:

• Extremely organized
• Comfortable taking initiative
• Naturally good at following up
• Curious and willing to research unfamiliar topics
• Comfortable working with an entrepreneur who generates lots of ideas
• Able to bring structure to sometimes-unstructured conversations
• Comfortable respectfully saying, “We still haven't finished this.”
• Good with Google Docs/Sheets or similar tools
• Comfortable using AI tools such as ChatGPT
• Reliable and able to work independently

You don't need to know everything about my businesses. Organization, judgment, curiosity and follow-through matter more to me than industry experience.

Time Commitment

Approximately 5 hours per week to start, with a flexible schedule.

We'll have a short weekly planning/review meeting, and the remaining time can generally be completed independently.

This will initially be a trial arrangement. If we work well together and the role creates value, there is potential for the responsibilities and hours to grow.

To Apply

Please send me a short introduction telling me about yourself and answer these three questions:

• Tell me about a time you helped an unorganized person, project or business become more organized.
• If I give you 10 ideas in one meeting, how would you make sure we don't start chasing all 10?
• If I repeatedly get distracted by new projects before finishing existing ones, how would you handle that?

I'm much more interested in your answers than receiving a generic cover letter.

Pay: $20.00-$35.00 per hour

Expected hours: 5.0 per week

Benefits:

• Flexible schedule

Work Location: Hybrid remote in Winnipeg, MB R2V 3C6