Executive Assistant to the CEO

About the Role

As a key member of the team, the Executive Assistant will be responsible for managing the CEO's complex calendar, coordinating with prospects to secure high-value meetings, and ensuring clear communication across all aspects of the role. With the company's focus on providing a fully remote work environment, the successful candidate will be comfortable working in a remote setting and managing their time effectively to meet the demands of the position.

The role is based in Canada, with a requirement to work overnight-shift hours, and offers a unique opportunity for a skilled Executive Assistant to join a talented and collaborative team and contribute to the company's continued growth and success.

What You Will Do

• Manage the CEO's complex calendar and act as a proactive appointment setter, coordinating with prospects to get high-value meetings on the books
• Own the CRM (Hubspot) by keeping data clean, managing the sales pipeline, and handling email triage to ensure no lead or priority falls through the cracks
• Attend key meetings to take detailed notes and ensure all resulting action items—especially those related to client follow-ups—are tracked and executed
• Assist with organizing business files, tracking project deliverables, and ensuring necessary documentation is current and accessible
• Conduct research on prospects and assist in preparing high-quality decks, documents, and proposals to help close deals
• Handle occasional personal administrative tasks, including complex travel bookings, expense reporting, or managing corporate/personal gifting
• Maintain confidentiality and exercise the highest level of discretion across all aspects of the role, protecting sensitive business and personal information
• Provide support for the CEO and the wider team as required, including preparing meeting materials and minutes
• Develop and implement processes to improve the efficiency and effectiveness of the CEO's workflow

What We Are Looking For

• 3+ years of proven experience as an Executive Assistant, Personal Assistant, or in a similar high-level support role
• Solid experience in Hubspot Power User and feel confident managing CRM workflows, contacting clients, and sales pipelines
• Excellent written and verbal communication skills, with a keen ability to articulate thoughts clearly and draft polished correspondence
• Proactive, detail-oriented, and a demonstrated ability to manage up and anticipate needs before they are stated
• Ability to work in PST working hours and adapt to the company's overnight-shift schedule
• Strong organizational and time management skills, with the ability to prioritize tasks and meet deadlines
• Ability to work in a remote setting and manage time effectively to meet the demands of the position

Nice to Have

• Previous startup and/or design agency experience
• Experience handling design requests for MSMEs, large corporations, and entrepreneurial initiatives
• Familiarity with Excel and other Microsoft Office applications
• Knowledge of project management principles and practices

Benefits and Perks

• Fully Remote Work: Enjoy the flexibility of a remote work environment
• Paid Time Off & Benefits: Generous paid time off, mental health leave, and comprehensive health coverage
• Professional Growth: Opportunity to grow with a talented and collaborative team
• Competitive Compensation: Competitive salary with yearly and surprise raises
• Equipment Allowance: Allowance provided to equip your home office
• Access to cutting-edge technology and tools to support your work

• Ensure you have a strong understanding of HubSpot and CRM management before applying, and be prepared to provide examples of your experience
• Develop a portfolio that showcases your ability to manage complex calendars, coordinate meetings, and provide high-level support
• Highlight your excellent written and verbal communication skills, and provide examples of times when you have had to articulate thoughts clearly and draft polished correspondence
• Be prepared to discuss your experience working in a remote setting and how you manage your time effectively to meet the demands of the position
• Research the company and the role thoroughly, and be prepared to ask informed questions during the interview process
• Consider obtaining certifications or taking courses to improve your skills in Excel, project management, and other relevant areas