Apply on Kit Job: kitjob.ca/job/2g9qf9

About Us

We help organizations build high-impact UX teams through expert design leadership, training, and talent placement. We are a human-centered, women-owned consultancy that values high-quality work and a playful, collaborative spirit.

About You

You are the steady operational force behind our remote-first team. You thrive on structure, anticipate needs before they are spoken, and love being the "connective tissue" between leadership and the rest of the world.

The Essentials

- 5+ years of progressive experience in an EA, HR Ops, or Office Ops role
- Winnipeg-based (required). Have a valid driver’s license and car
- Experience in remote/hybrid skilled services or tech environments
- A positive "figure it out" mindset with high discretion and autonomy

This Role Is For You If

- You love bringing structure and follow-through to the moving parts of a growing business
- You anticipate needs before they're spoken and take quiet pride in a well-run process
- You handle sensitive information thoughtfully and know when to escalate with care
- You enjoy being the connective tissue between leadership, teammates, and external partners
- You see problems as puzzles, and "figuring it out" is one of your favourite phrases.
- You want your scope, autonomy, and decision-making authority to grow over time as you build trust and demonstrate what you can do

Your Typical Day





Reporting to the CEO and Director of Finance, you will own the workflows that keep us running:

- Executive Support: Manage the CEO’s calendar, prep meeting materials, and drive follow-ups.
- Onsite support: Provide occasional admin assistance at the CEO’s residence, including expense reconciliation, shipping/mailing logistics, and miscellaneous business tasks.
- People Ops: Own end-to-end onboarding/offboarding, maintain HR documentation, and track PTO/compliance
- IT & Systems: Coordinate hardware/software access, manage vendors, and triage day-to-day IT issues
- Culture & Events: Plan team-building, travel, and internal events to keep our culture vibrant.

What You’ll Love About Us

- Human-Centered Culture: 100% women-owned and WBE Canada certified.
- True Balance: A strict "Disconnect From Work" policy for evenings and weekends.
- Growth Support: Yearly professional development funds and a remote-work stipend.
- Full Benefits: Comprehensive health program and a Wellness Spending Account.
- Authenticity: A team that actually lives its values (and enjoys it).

Sound like you?

We'd love to meet you. Send your resume and a brief note on why you’re the perfect fit to .

Outwitly is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Apply on Kit Job: kitjob.ca/job/2g9qf9

📌 Executive Assistant Office Manager (Winnipeg)
🏢 Appcast
📍 Winnipeg