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 key 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

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