Executive Assistant

Executive Assistant

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Winnipeg, Manitoba

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Office Professionals

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Permanent

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10/01/2026

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286149

Stacey Danley at Aplin has partnered with our client, a boutique financial planning firm, on the search for a term Executive Assistant position.

This is an opportunity to join a lean, collaborative and high-performing environment where trust, autonomy and flexibility are genuinely valued. You’ll work closely with senior professionals, clients and internal partners, serving as the organizational hub that keeps priorities moving and ensures a seamless experience for everyone involved.

The successful candidate will be someone who is one step ahead—highly organized, confident making decisions, and comfortable taking ownership without needing to be asked. This is not a role where you’ll simply manage a calendar; you’ll become a trusted partner who anticipates needs, solves problems and looks for smarter ways of working.

What You’ll Do
  • Provide proactive, high-level administrative support to two partners
  • Manage complex calendars, scheduling, meetings and competing priorities
  • Serve as a trusted point of contact for clients and internal stakeholders
  • Coordinate correspondence, follow-ups and day-to-day workflows
  • Anticipate needs and proactively address issues before they become problems
  • Identify opportunities to improve processes and enhance efficiency
  • Embrace technology and AI tools to streamline workflows and work smarter
  • Contribute wherever needed to help the broader team operate effectively
What You Bring
  • 3+ years of experience supporting senior leaders in an Executive Assistant or similar capacity
  • Exceptional organizational skills and the ability to confidently manage competing priorities
  • A polished, professional communication style and strong client-service orientation
  • Initiative, sound judgment and a high degree of independence
  • A natural ability to anticipate what’s needed rather than waiting to be asked
  • Strong Microsoft 365 skills, including Outlook, Teams, SharePoint and OneDrive
  • Curiosity and confidence with technology, CRM systems and AI tools
  • Experience within financial services, wealth management or another professional services environment is an asset
  • Post-secondary education or equivalent professional experience
Benefits and Perks
  • Competitive compensation and performance bonus
  • Comprehensive benefits
  • Flexible environment
  • Long-term growth potential
  • Convenient location west of downtown with free parking



At Aplin — together with our brands CompuStaff, Impact Recruitment, and Vantix Systems — we connect great people with great organizations across North America. We believe diverse teams build stronger companies, and we welcome applicants from all backgrounds, experiences, and perspectives. We use AI tools to assist in a fair and efficient matching process, helping our recruiters connect the right people with the right opportunities. To be considered, applicants must be legally entitled to work in Canada, including holding any required permits. Our recruitment services are always free for job seekers. Accommodation is available upon request throughout all stages of the recruitment process.

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