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Career Resources:

Executive Operations (AI + Project Coordination) | In Person | Winnipeg
Upper Edge Property Management Inc.
Winnipeg, MB R3T 0P4
•
Hybrid work
$20–$40 an hour
Part-time, Permanent
Apply now

Job details

Here’s how the job details align with your profile.

Pay

$20–$40 an hour

Job type

Part-time
Permanent

Benefits

Pulled from the full job description
Paid time off
Vision care
Dental care
Employee assistance program
RRSP match
Extended health care
Wellness program

Full job description

Job Summary

We are seeking a high energy and highly organized person to assist Garret Wong, Founder of 4 private companies, with the hopes that the successful candidate will eventually grow into a full time Chief of Staff. This part-time, in-person role based in Winnipeg will eventually transition to a full time position and offers a focus on AI integration and project coordination. an exciting opportunity to support daily operations, manage administrative tasks, and contribute to innovative projects within a fast-paced environment. If you thrive in a multitasking role that combines clerical expertise with technological savvy, this position is perfect for you!

Company Overview

Upper Edge Property Management Inc. is a forward-thinking third-party property management company with over 30 years of industry leadership. We are dedicated to innovating and streamlining property management processes by integrating the latest technologies to enhance the experience for property owners and tenants alike.

What this role is

This is a high trust role working directly with the founder. You will have full control over email and calendar and will control access to the founder. Your job is to keep work moving, close loops, and make sure delegated projects actually finish.

This is not a personal errands role. If you are looking for household assistant work, this is not a fit.

Responsibilities

You will own five outcomes:

Project follow through across staff

  • Oversee small delegations and operational projects assigned to other team members

Research to decision to execution

  • Look up things that would take the founder 15 to 20 minutes

Stakeholder follow up and completion

  • Example scenario: a bank or vendor needs authorization
  • Draft the permission letter or email

Email and calendar gatekeeping

  • Triage inbox, draft replies, request missing info, and escalate only what matters

AI assisted operations and documentation

  • Oversee Agentic AI Employee creation by communicating the vision of the Founder to various stakeholders and report back milestones from the Project Management software engineering platform to the Founder
  • Communicate revisions back to the stakeholders as delegated
  • Ensure the Founder's personal AI Assistant's output is correct by assisting in audits

Experience

  • Proven clerical or administrative experience in an office setting with strong organizational skills.
  • Familiarility with Artificial Intelligence, and other LLMs such as Claude, Gemini, ChatGPT
  • Working vocabulary and working knowledge of "vibe" coding and the principles behind building Agentic AI Agents
  • Familiarity with Linear or similar project management software preferred
  • Strong typing skills with attention to detail for data entry and proofreading tasks.
  • Restaurant and hospitality experience an asset

Tools you will use

  • Monday.com for operational task tracking
  • Linear for software engineering tasks and issue tracking
  • Google Workspace
  • AI tools (Claude Code, Github, MCP/API Servers) daily

You are a fit if

  • You are highly organized and enjoy owning systems
  • You can write clearly and follow up without being asked
  • You are comfortable around software projects and technical vocabulary (even if you are not a full time developer)
  • You like being the person who closes loops and keeps standards high

Minimum requirements

  • In person in Winnipeg with reliable car
  • Typing speed: 40 WPM or higher
  • Strong written communication
  • Comfortable with AI workflows and basic software project concepts

Preferred

  • Experience with Monday.com, Linear, Notion, Jira, ClickUp, or similar
  • Exposure to product or engineering workflows: backlog, sprint, bug, feature, QA
  • Prior admin, coordinator, or hospitality experience where you had to juggle multiple priorities

What success looks like (first 30 days)

  • Inbox and calendar are organized: fewer missed details and fewer interruptions
  • Every delegated task has an owner, due date, and written next step
  • The founder receives a daily summary: decisions needed, blockers, and progress
  • Stakeholder loops close fast: bank, vendors, internal staff
  • Monday.com and Linear are current and trusted as the source of truth

Join us to be part of a vibrant team dedicated to operational excellence! This role offers the chance to develop your skills in project coordination while supporting innovative AI initiatives within a collaborative environment.

Pay: $20.00-$40.00 per hour

Expected hours: 15.0 per week

Benefits:

  • Company events
  • Dental care
  • Employee assistance program
  • Extended health care
  • Flexible schedule
  • On-site parking
  • Paid time off
  • RRSP match
  • Vision care
  • Wellness program
  • Work from home

Work Location: Hybrid remote in Winnipeg, MB R3T 0P4

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