Personal & Executive Assistant

WiredCandy Ventures is an early-stage technology venture capital firm dedicated to launching and supporting high-potential startups driven by the rapid adoption of technology. We partner with exceptional founders from the earliest stages, helping transform bold ideas into successful, market-leading businesses. Our strength lies in our teams diverse experience, deep industry knowledge, and a shared commitment to innovation. Our head office is located in Toronto, with a vibrant network of companies across North America.

Job Description We are seeking a highly organized and proactive Personal & Executive Assistant to support two C‑level executives. This position is primarily a personal assistant and household‑oriented role, with executive assistant responsibilities as a secondary component. You will manage a wide range of personal, family, household, property, and administrative tasks. The ideal candidate is adaptable, kid‑friendly, detail‑oriented, and capable of managing responsibilities independently. This role requires a reliable vehicle and the ability to travel occasionally to Collingwood.

Primary Responsibilities: Personal Assistant & Household Support Family & Children Management

Maintain school calendars, important dates, and activity schedules

Handle school forms, sign‑ups, and program registrations

Support with daily school pickup and drive children to activities

Assist with afternoon responsibilities when children are present

Household Operations

Run personal errands (returns, gifts, and similar tasks)

Plan and coordinate children’s birthday parties including vendor bookings

Communicate with household staff and coordinate schedules

Oversee vendors, contractors, and maintenance appointments

Ensure daily household operations run smoothly

Property Support

Serve as a communication bridge between tenants and the executives

Coordinate service providers for repairs and property needs

Organize and process property‑related invoices and receipts

Organization & Tax Season Support

Reconcile property‑related payments across multiple properties

Maintain documentation needed for personal and property tax season

Prepare statements, receipts, and support packages for accountants

Manage calendars for two C‑level executives

Schedule meetings, calls, and interviews

Prepare and manage expense reports

Draft and edit correspondence and documents

Prepare for board meetings

Support logistics for company‑wide events

Liaise with internal teams and external partners

Provide general administrative support and problem‑solving

What We’re Looking For:

Exceptional written and verbal communication skills

Strong interpersonal abilities and a positive, professional attitude

Highly organized with a strong attention to detail

Ability to multitask, shift priorities quickly, and work independently

Flexible availability; occasional evenings and weekends

Must be comfortable driving children

Strong knowledge of Mac and Google Workspace

Bookkeeping or financial organization experience is an asset

Must have a reliable car, insurance, and a good driving record

Must be a Canadian citizen or have the legal right to work in Canada

Commitment to confidentiality (NDA required)

A fun‑loving, supportive environment where people are challenged and expected to grow

WiredCandy Ventures is an equal opportunity, affirmative action employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability, or any other characteristic protected by law.

If you are an individual with a disability and require a reasonable accommodation to complete any part of the application process, or are limited in the ability or unable to access or use this online application process and need an alternative method for applying, you may contact us for assistance.

We thank all applicants in advance for their interest in this position, however, only those selected for an interview will be contacted.

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