Executive Assistant

About Dialogue

Dialogue is the #1 virtual care provider in Canada. By developing our Integrated Health Platform🅫, we provide exceptional online health and wellness programs (primary care, mental health, iCBT, EAP, and wellness) to organizations that want to improve the wellness of their employees and families.

When it comes to our work, we set the bar high. Together, we’re transforming health and helping millions improve their well-being. We’re firm believers that great people don’t settle on:

• Impact
• Community
• Growth
• Excellence

Feel like you can make a difference? Good news, we saved you a seat! 

Come as you are. As a proud equal-opportunity employer, Dialogue is dedicated to creating a diverse and inclusive workplace for everyone. Qualified applicants will be considered regardless of citizenship, ethnicity, race, colour, religion, gender, gender identity or expression, sexual orientation, disability, age, or veteran status. Applicants who require specialized accommodation are encouraged to contact [email protected].

Executive Assistant

We are looking for an exceptionally organized, proactive, and service-oriented Executive Assistant to support Dialogue’s C-Suite executives while also owning the day-to-day operations of our Toronto office. This is an EA-first role with facilities and office operations responsibilities that ensure our leaders, and our Toronto workspace, run smoothly and efficiently.

You will play a critical role in enabling our executives to perform at their best, while creating a warm, seamless, and collaborative in-office experience for employees and guests. This role requires presence in our Toronto office 5 days a week to support both executive needs and office operations.

What you'll be doing

• Manage complex calendars and schedules for two C-Suite executives, including meeting coordination, room bookings, video conference logistics, and travel arrangements
• Monitor inboxes and email communications, drafting and responding on behalf of executives when appropriate
• Prepare briefing materials, internal communications, decks, and documentation as needed
• Support with expense reports, contact management, procurement, and contract routing
• Coordinate executive involvement in internal meetings, company-wide initiatives, and external engagements
• Exercise sound judgment, discretion, and confidentiality at all times
• Offer occasional personal assistance when required
• Proactively identify opportunities to streamline administrative processes and tools

• Oversee daily operations and maintenance of our Toronto office to ensure a safe, organized, and welcoming workplace
• Manage vendor relationships (cleaning, building support, IT, catering, supplies, etc.) and monitor related budgets
• Support procurement of supplies, equipment, and furniture; maintain inventories and shared spaces
• Coordinate internal events, meetings, and in-office activities that contribute to a vibrant team culture
• Provide basic technical support for office tools, Zoom Rooms, conference equipment, and visitor systems
• Support the development and compliance of office policies, emergency procedures, and health & safety standards
• Greet employees and guests, ensuring a polished and professional in-office experience
• Play a key role in supporting future office moves or expansions in Toronto, including vendor coordination and logistics

We'd love to hear from you if you have

• Availability to work on-site 5 days/week to support both executives and the office
• 3+ years of direct executive support experience, ideally supporting senior leaders in a fast-moving environment
• Experience managing office operations, facilities, workplace experience, or vendor/space coordination (asset)
• Outstanding verbal and written communication skills in English
• High EQ, empathy, generosity, and a genuine enjoyment of helping others succeed
• Ability to anticipate needs and take initiative with minimal direction
• Strong organizational skills, attention to detail, and ability to juggle multiple priorities
• Proven professionalism, discretion, and confidence handling sensitive and confidential information
• Tech-savviness — Google Suite, conferencing systems, Zoom Rooms, procurement, etc.
• A positive, service-oriented, and collaborative attitude

At Dialogue, your well-being is our priority

Taking care of others also means taking care of our team! Depending on your role and employment status, you could have access to the following benefits:

• Access to the Dialogue app and virtual mental health support for you and your family
• Fully funded insurance, a health spending account, dental coverage, and fitness reimbursement
• 4 weeks vacation, 9 wellness days, and 1 volunteer day
• Hybrid work: 3 days/week in our Montreal or Toronto offices, excluding remote roles
• Work abroad up to 4 weeks/year
• Incentive plans, referral bonuses & RRSP matching
• Learning via Coursera, external training budget & mentorship
• Optional parental leave top-up