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Sunny Side Investments Inc.Verified Job Source

Executive Assistant & Office Manager

  • Toronto, ON
  • Hybrid
  • Posted Oct 2, 2026
  • 1 position

$85,000–$120,000 / year

Opens an external site

Employment type
Full-time
Experience level
Senior · 5+ years
Apply by
Oct 30, 2026
Posting language
English
Working hours
40 hours per week
Seniority
Mid-Senior level
Application method
Direct apply is available

Job summary

Manage the principals’ complex calendars, correspondence, documents, expenses, meetings, travel, and office operations. Coordinate with professional advisors, vendors, and household staff, track commitments, and handle personal requests with strict confidentiality.

Job details

About the Role A newly-formed private family office in Toronto is seeking a highly organized, discreet Executive Assistant and Office Manager to support the principals across business and personal matters. This position reports to the CEO and President, offers room for growth and the exciting opportunity to shape the foundation of a substantial family office. This is a high-trust role at the centre of the family's affairs, requiring sound judgment, absolute confidentiality, and the ability to manage complexity calmly and independently. Although availability during regular business hours is generally expected, the principals value productivity and timely results over hours worked. As such, the role permits reasonable flexibility to accommodate lifestyle needs. Responsibilities Manage complex calendars, scheduling, and correspondence for the principal(s) Manage day-to-day needs of the office (e.g. maintain office supply stock, coordinate and attend meetings with vendors) Handle internal and external correspondence Prepare and organize documents, expense reports, and meeting materials Act as liaison with advisors, lawyers, accountants, vendors, and household staff Track deadlines, follow-ups, and commitments across business and personal matters Handle ad hoc personal and lifestyle requests as they arise Coordinate domestic and international travel, including itineraries and logistics Maintain strict confidentiality and discretion at all times Requirements 5+ years as an Office Manager and Executive or Personal Assistant supporting a family office Exceptional organizational and prioritization skills; proactive and anticipatory Willingness to get the job done, big or small Strong written and verbal communication with attention to detail Proficiency with Microsoft Office Preferred/Not Required Bookkeeping experience & familiarity with accounting software (QBO) Experience handling AP/AR Compensation: CA$85,000.00-CA$120,000.00 per year Reports to: Family Office President & CEO Location: Toronto, ON (in-office / hybrid) | Type: Full-time, permanent Applications will be handled in strict confidence.

What you’ll do

Manage the principals’ complex calendars, correspondence, documents, expenses, meetings, travel, and office operations. Coordinate with professional advisors, vendors, and household staff, track commitments, and handle personal requests with strict confidentiality.

Requirements

Requires at least five years of experience as an Office Manager and Executive or Personal Assistant supporting a family office. Candidates should demonstrate exceptional organization and prioritization, proactive judgment, strong written and verbal communication, attention to detail, and proficiency with Microsoft Office; bookkeeping, QBO, and AP/AR experience are preferred but not required.

Listed skills

  • written communication · Preferred
  • Organization · Preferred
  • Attention to detail · Preferred
  • Microsoft Office · Preferred
  • Prioritization · Preferred
  • scheduling · Preferred
  • Bookkeeping · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

  • Calendar Management
  • Scheduling
  • Correspondence Management
  • Office Management
  • Organization
  • Prioritization
  • Proactive Planning
  • Written Communication
  • Verbal Communication
  • Attention to Detail
  • Confidentiality
  • Discretion
  • Travel Coordination
  • Expense Reporting
  • Microsoft Office
  • Bookkeeping

Job areas

  • Administrative
  • Management & Leadership
  • Finance & Accounting

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