Executive Assistant coordinating confidential administration for Manitoba Public Insurance’s President and Executive team. Managing schedules, workflows, correspondence, and Executive Committee meetings onsite in Winnipeg.
About the role
- Remote Executive Assistant organizing a founder-led company CEO’s calendar, reporting, sales, and content operations. Building systems that protect his time and keep client work moving.
Responsibilities
- Own and defend the CEO's calendar and build the day around highest-value work
- Run a daily priority list
- Triage inboxes and messages, flagging issues and closing loops
- Track deliverables, approvals, and decisions waiting on the CEO
- Drive turnaround on client creative strategy and prevent client work from stalling
- Collect, review, and present concise company reporting digests
- Coordinate team follow-ups so approvals and decisions keep moving
- Schedule and prepare high-value sales calls, consultations, and coaching calls
- Prepare briefing notes, update the CRM, and manage follow-ups
- Keep the social media content pipeline on schedule
- Coordinate recording blocks, editors, team members, and the publishing calendar
- Support launches and delivery of coaching and consultation offers
- Book business travel and build itineraries
- Handle business administration, documents, agreements, and expense tracking
- Build and maintain trackers, SOPs, checklists, and recurring process documentation
Requirements
- 3+ years as an Executive Assistant, Chief of Staff or equivalent to a founder, CEO or senior executive, ideally in a fast-growing or entrepreneurial company
- Proven remote experience running an executive's day without being in the room
- Fluent professional English, written and spoken
- Ability to work US Eastern Time business hours consistently
- Reliable internet and a quiet workspace
- Strong administrative and operational backbone; ability to build systems
- Exceptional discretion with confidential business and financial information
- Fluency with Google Workspace, Slack, a project management tool (ClickUp, Notion or equivalent), a CRM, spreadsheets, and daily use of AI assistants
- Direct, unflappable, and comfortable with a straightforward, high-energy, fast-moving principal
- Willingness to push back and hold the CEO accountable
- Experience in a marketing agency, paid ads or creative production environment (nice to have)
- Social media or content operations experience (nice to have)
- Experience supporting a founder who sells coaching, consulting or premium offers (nice to have)
Benefits
- Paid Time Off
- Fully remote work
- Direct mentorship from the CEO
- Clear path to grow into a Chief of Staff position
- Exposure to high-impact leaders
Job title
Job type
Experience level
Salary
Not specified
Degree requirement
No Education Requirement
Location requirements
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