Stalwart Insurance Brokers Ltd. (Stalwart) is a growing national life insurance brokerage and financial services provider with a focus on high-complexity client and business situations. Stalwart values excellence and entrepreneurial thinking, and requires staff with the capacity to solve complex, novel problems. Stalwart is growing rapidly and intends to sustain this rapid growth through the addition of ambitious team members looking to rapidly scale their skills, abilities, and relationships, and contribute to a high-performing corporate finance team.

Summary

We are looking for an Administrative Assistant to join our team and provide day-to-day administrative support to senior leadership. This role is ideal for someone who is highly organized, proactive, and able to manage multiple priorities in a fast-paced workplace. The successful candidate will be trusted with confidential information, have exceptional attention to detail, and be comfortable working independently. Role Overview

Your responsibilities will include

Managing executive calendars, scheduling meetings, and coordinating appointments. Monitoring and managing executive email inboxes, including drafting responses and prioritizing communications. Coordinating travel arrangements and preparing itineraries. Preparing, formatting, and proofreading correspondence, reports, presentations, and other business documents. Organizing and maintaining electronic files and records. Providing general administrative support,



including data entry, expense reporting, and document management. Supporting senior leadership with day-to-day administrative needs and special projects. Handling confidential and sensitive information with professionalism and discretion. Assisting with other administrative duties as assigned.

Required Skills and Experience

Exceptional organizational and time management skills, with the ability to manage multiple priorities and deadlines. Excellent written and verbal communication skills. Strong attention to detail and a high degree of professionalism and discretion. Proficiency with Microsoft Office (Outlook, Word, Excel, and PowerPoint) and Google Workspace. Ability to work independently while collaborating effectively with others.

Experience managing executive calendars and email correspondence is a strong asset. A valid driver's license (essential). Compensation

$70,000 per year (prorated). Role eligible for bonus, depending on individual and company performance. Position Type

Nature: Temporary (2-4 weeks with possibility of Permanent extension), full-time, in-person position Time Commitment: High-commitment position with overtime required as needed. Start Date: Immediate. Human-led hiring process

Application review 01 A person reviews the application. No automatic rejection is enabled. Structured conversations 02 Interview evidence follows an approved, role-specific plan.

📌 Administrative Assistant (Winnipeg)
🏢 The Personality Project
📍 Winnipeg