Executive Assistant

Role overview

An award-winning technology company is hiring a polished and highly organized Executive Assistant to support two senior leaders. The organization builds software that helps businesses exchange confidential files securely and efficiently, with a focus on privacy, compliance, and easy client collaboration. The team is a mature startup of about 25 people that operates in scale-up mode and values a high-performing, collaborative, and enjoyable work environment.

This is a full-time permanent position based in Toronto, Ontario, near Exhibition GO Station. The role is primarily in-office, with work expected on site four days per week. It suits someone who can stay calm under pressure, manage many moving parts, and be trusted with sensitive information, scheduling, travel, numbers, vendors, and team coordination.

Compensation and benefits

The role offers a base salary of $65,000 to $75,000, plus an annual performance bonus of 10% to 12% and comprehensive health and dental coverage. Additional package details include 3 weeks of vacation, 3 paid sick days, and benefits that begin after 30 days.

Key responsibilities

• Provide high-touch, dedicated support to two senior executives while managing and improving their fast-moving calendars so time stays protected for strategic priorities.
• Arrange end-to-end travel for the executives and for group travel involving sales and marketing teams, typically for groups of 1 to 10 people attending events.
• Handle expense submissions and related financial tracking carefully and accurately.
• Support one-off projects, coordinate with vendors and service providers, and keep external relationships moving smoothly.
• Serve as an on-site event coordinator, including occasional travel within Canada and to the United States.
• Prepare leaders for meetings by building agendas, assembling briefing materials, and tracking follow-up actions.
• Contribute to team morale and culture by organizing office socials, lunches, milestone celebrations, and internal events.
• Act as a professional point of contact and gatekeeper for clients, partners, vendors, and internal stakeholders while maintaining strict confidentiality.

Required qualifications

• 3 to 6 years of experience as an Executive Assistant, administrative assistant, or in a similar operations-focused role, preferably in SaaS or a corporate professional services setting.
• Direct experience coordinating travel, including group travel, flights, transportation, and ground logistics.
• Strong command of Excel and comfort working with numbers, expense records, and financial reporting.
• Excellent English communication skills; native-level English is strongly preferred.
• A professional presence, solid business judgment, and the confidence to interact with everyone from frontline staff to senior executives.
• Strong discretion and emotional intelligence when dealing with confidential or proprietary information.
• Ability to work independently, learn quickly, solve problems on the fly, and succeed in a fast-paced scaling environment.
• A collaborative mindset and willingness to step in wherever needed.
• Comfort using Microsoft Word, PowerPoint, Excel, and Google Workspace.

Additional information

This is a permanent, full-time role. The work location is Toronto, Ontario, near Exhibition GO Station, with an in-office schedule of 4 days per week. The employer is an equal opportunity employer and can provide accommodations at any stage of the hiring process.

About the company

The company is an award-winning tech business whose platform supports secure file sharing and confidential client communication. It is focused on improving productivity, security, and compliance while giving talented people room to make an impact in a fun, diverse, and high-performing team.