Executive Assistant (Senior Leadership)

Job Responsibility:

About the role We're looking for a proactive, detail-obsessed, and unflappable Executive Assistant to support the Vice President responsible for implementing the Entrepreneurial Operating System (EOS) across multiple business units in Canada and the U.S. This is not your average admin role — it's for someone who thrives in a fast-paced, high-accountability environment and is passionate about bringing order to complexity. This role is pivotal in ensuring the smooth operation of our office and supporting key initiatives.

What You'll Be Doing:

• Calendar Management : Own a complex calendar — prioritize, book, and shift meetings strategically.
• Email & Communications Triage : Filter, flag, and manage the VP's inbox. Draft and send internal communications, memos, and follow-ups.
• Meeting Support : Schedule, confirm, prep materials for, and take notes at key meetings (EOS Level 10s, department meetings, etc.).
• Travel & Offsite Logistics : Coordinate travel itineraries, accommodation, and full agendas for site visits, offsites, and leadership meetings.
• Corporate Event Coordination : Support the planning and execution of internal corporate events and team engagement initiatives.
• Project & Priority Support : Help track EOS rocks and milestones, manage reminders, and assist with accountability follow-through.
• Gatekeeping & Decision Buffering : Be a thoughtful gatekeeper for the VP's time and energy — help prioritize what matters most.

What We're Looking For:

• 5+ years of experience as an Executive Assistant or in a similar high-paced support role (bonus if you've supported C-level leaders)
• Excellent written and verbal communication skills (you'll be drafting memos and messages that reflect our values)
• Master organizer — able to manage multiple moving parts without letting anything slip
• Calm under pressure, with a solution-oriented mindset
• Discretion and trustworthiness handling sensitive information
• Tech-savvy: Proficiency with Microsoft Office Suite, Teams, Outlook, and calendar/email management tools

Nice-to-Haves:

• Experience working in an EOS-run organization
• Event coordination or executive project management experience
• Familiarity with cross-border scheduling or U.S./Canada business practices

What You'll Get:

• A seat at the table — your work directly supports strategic operations across North America
• A culture that values communication, initiative, and ownership
• Competitive salary (based on experience), extended benefits, and profit sharing
• The chance to make a big impact in a growing, multi-industry organization with strong family roots and entrepreneurial spirit

Join our team as an Executive Assistant where you will play a vital role in supporting our leadership while contributing to the overall success of our organization. We look forward to welcoming a dedicated professional who thrives in a dynamic environment.

Job Type: Full-time

Benefits:

• Dental care
• Extended health care
• Paid time off
• Profit sharing

Schedule:

• Monday to Friday

Application question(s):

• What is your salary expectation for this role?

Education:

• Secondary School (preferred)

Experience:

• High level executive leadership support: 3 years (required)

Work Location: In person

Application deadline: 2025-05-01