Job Description
Executive to the President/CEO
Location: Winnipeg, MB (2070 Logan Ave)
Employment Type: Full-Time, Permanent
Shift: Day shift
About us:
We are seeking a highly experienced, proactive, and discreet Executive Assistant to the CEO/President. This role is a true blend of Executive Assistant and Personal Assistant, providing comprehensive administrative, operational, and personal support to ensure the CEO’s workday and priorities run seamlessly.
This is not an entry‑level role. The successful candidate will be confident operating independently, anticipating needs without reminders, and handling sensitive information with absolute confidentiality. You will play a critical role in supporting CEO‑led priorities across multiple business units in Canada and the U.S.
Key Responsibilities
Executive & Personal Support
Manage the CEO’s professional and personal calendars, including appointments, commitments, and schedule changes
Handle personal administrative tasks, including quarterly benefits submissions, prescription receipts, and related paperwork
Prepare the CEO for daily readiness: morning coffee, organized workspace, printed materials, and proactive setup
Ensure boardrooms and meeting technology are fully prepared (Teams, AV, meeting materials) prior to meetings
Act as a trusted gatekeeper, filtering requests and protecting the CEO’s time and focus
Communications & Leadership Support
Triage and manage the CEO’s inbox, prioritizing and drafting responses as needed
Draft CEO announcements, internal communications, speaking notes, and talking points
Coordinate administrative support for CEO‑led priorities and initiatives
EOS & Meeting Support
Provide direct support for the Entrepreneurial Operating System (EOS), including:
Scheduling and preparing L10s, Quarterlies, and Annuals
Tracking Rocks, Scorecards, and action items
Documenting and following up on meeting outcomes
Logistics & Coordination
Coordinate travel itineraries, accommodations, and schedules for business travel
Provide light support to internal culture and morale initiatives as needed
Prepare agendas, meeting materials, notes, and follow‑up items
What We’re Looking For
5+ years of experience as an Executive Assistant supporting senior leaders (C‑suite experience strongly preferred)
Proven ability to operate independently and proactively without learning the role on the job
Exceptional organization, time management, and attention to detail
Strong written and verbal communication skills
Absolute discretion and professionalism when handling confidential information
Calm, solution‑oriented mindset in fast‑paced environments
Strong technical skills (Microsoft Office Suite, Outlook, Teams, calendar/email management tools)
Key Competencies
High attention to detail and accuracy
Deadline‑driven and organized
Strong customer service orientation
Problem-solving and analytical ability
Ability to handle confidential information with discretion
What We Offer:
Direct partnership with the President/CEO
Competitive compensation: A fair and market‑aligned wage structure.
Comprehensive benefits: Group Health and Dental Benefits to support employee well‑being.
Retirement savings: Group RRSP Plan with employer contributions.
Employee incentives: Additional programs that reward performance and commitment.
Training and development: On‑the‑job training provided for the right candidate.
Job Type: Full-time
Pay: From $80,000.00 per year
Benefits:
Company events
Dental care
Disability insurance
Employee assistance program
Extended health care
Life insurance
On-site parking
Profit sharing
RRSP match
Vision care
Work Location: In person
Location: Winnipeg, MB (2070 Logan Ave)
Employment Type: Full-Time, Permanent
Shift: Day shift
About us:
We are seeking a highly experienced, proactive, and discreet Executive Assistant to the CEO/President. This role is a true blend of Executive Assistant and Personal Assistant, providing comprehensive administrative, operational, and personal support to ensure the CEO’s workday and priorities run seamlessly.
This is not an entry‑level role. The successful candidate will be confident operating independently, anticipating needs without reminders, and handling sensitive information with absolute confidentiality. You will play a critical role in supporting CEO‑led priorities across multiple business units in Canada and the U.S.
Key Responsibilities
Executive & Personal Support
Manage the CEO’s professional and personal calendars, including appointments, commitments, and schedule changes
Handle personal administrative tasks, including quarterly benefits submissions, prescription receipts, and related paperwork
Prepare the CEO for daily readiness: morning coffee, organized workspace, printed materials, and proactive setup
Ensure boardrooms and meeting technology are fully prepared (Teams, AV, meeting materials) prior to meetings
Act as a trusted gatekeeper, filtering requests and protecting the CEO’s time and focus
Communications & Leadership Support
Triage and manage the CEO’s inbox, prioritizing and drafting responses as needed
Draft CEO announcements, internal communications, speaking notes, and talking points
Coordinate administrative support for CEO‑led priorities and initiatives
EOS & Meeting Support
Provide direct support for the Entrepreneurial Operating System (EOS), including:
Scheduling and preparing L10s, Quarterlies, and Annuals
Tracking Rocks, Scorecards, and action items
Documenting and following up on meeting outcomes
Logistics & Coordination
Coordinate travel itineraries, accommodations, and schedules for business travel
Provide light support to internal culture and morale initiatives as needed
Prepare agendas, meeting materials, notes, and follow‑up items
What We’re Looking For
5+ years of experience as an Executive Assistant supporting senior leaders (C‑suite experience strongly preferred)
Proven ability to operate independently and proactively without learning the role on the job
Exceptional organization, time management, and attention to detail
Strong written and verbal communication skills
Absolute discretion and professionalism when handling confidential information
Calm, solution‑oriented mindset in fast‑paced environments
Strong technical skills (Microsoft Office Suite, Outlook, Teams, calendar/email management tools)
Key Competencies
High attention to detail and accuracy
Deadline‑driven and organized
Strong customer service orientation
Problem-solving and analytical ability
Ability to handle confidential information with discretion
What We Offer:
Direct partnership with the President/CEO
Competitive compensation: A fair and market‑aligned wage structure.
Comprehensive benefits: Group Health and Dental Benefits to support employee well‑being.
Retirement savings: Group RRSP Plan with employer contributions.
Employee incentives: Additional programs that reward performance and commitment.
Training and development: On‑the‑job training provided for the right candidate.
Job Type: Full-time
Pay: From $80,000.00 per year
Benefits:
Company events
Dental care
Disability insurance
Employee assistance program
Extended health care
Life insurance
On-site parking
Profit sharing
RRSP match
Vision care
Work Location: In person
💡 Quick Summary
Seeking a career-building opportunity? The Executive Assistant to the President/CEO position is now open for candidates interested in the Admin Executive sector. This role in Winnipeg offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in Admin Executive is a plus.
