Jobs in Winnipeg, Canada

Job Title: Personal & Executive Assistant

Job Type: Part-time / Remote

Work Hours: 18–20 hours per week

Job Overview:

We’re helping our client find a highly organized and proactive Personal & Executive Assistant to provide both professional and personal support. This role blends executive-level administrative responsibilities with wellness and accountability support, making it ideal for someone who thrives on variety and enjoys being both a strategic partner and a supportive presence.

You’ll play a key role in ensuring smooth day-to‑day operations, handling business communications and scheduling while also helping the client stay consistent with personal goals, habits, and lifestyle management.

• Manage complex executive calendars, inboxes, and communications across multiple time zones.
• Draft and send professional correspondence on behalf of the executive.
• Plan and coordinate virtual meetings, calls, and events.
• Prepare reports, presentations, and meeting summaries.
• Serve as the first point of contact for internal and external stakeholders.
• Conduct research, manage contacts, and support business development (e.g., introductions, follow-ups).
• Maintain organized systems for documents, files, and communications.
• Tech tasks: experience with Slack + Gmail, and ideally knowledge of social media, funnels, and landing pages.

• Act as an accountability partner, providing gentle reminders and encouragement to maintain personal habits and goals.
• Assist with planning personal events, trips, and appointments.
• Source services, shop for products, or identify experiences that enhance lifestyle and wellbeing.
• Provide a calm, encouraging, and professional presence — blending the role of assistant and supportive coach.

• 3–5+ years of experience as an Executive Assistant, Personal Assistant, or similar role, preferably supporting C‑level or senior executives.
• Based in EST time zone (Toronto preferred) with availability during core business hours and flexibility for travel‑related adjustments.
• Strong written and verbal communication skills; excellent professionalism and discretion.
• Highly organized, detail‑oriented, and able to juggle multiple priorities.
• Proficient in productivity tools: Google Workspace, Microsoft Office, Slack, Zoom, and project management tools (Asana, Trello, or similar).
• Tech‑savvy with the ability to learn new tools quickly.
• Positive, proactive energy with an ability to provide both strategic executive support and personal/wellness accountability.
• Discreet and trustworthy with sensitive or confidential information.