Executive Assistant / Chief of Staff — Business Partner & Strategic Right Hand

The Little Campus; Toronto; Remote; CAD 80,000 - 100,000; Full time

Job summary

An educational organization in Toronto is seeking an exceptional Executive Assistant. This role goes beyond traditional tasks, focusing on strategic initiatives while enhancing the COO's productivity. The ideal candidate excels in critical thinking, possesses exceptional problem-solving skills, and showcases flawless communication. A monthly salary ranging from USD $2,000 to $3,500 will be offered for this fully remote position. Detailed cover letter and resume required for application.

Qualifications

• Must analyze complex situations and develop strategic solutions.
• Comfortable making judgment calls and defending reasoning behind decisions.
• Proven ability to quickly master new domains and skill sets.
• Creates clear processes and maintains comprehensive records.

Responsibilities

• Manage vendor lifecycle and financial operations.
• Lead cross-functional initiatives with minimal guidance.
• Draft important communications and proposals.
• Handle complex bureaucratic processes and novel problem-solving.

Skills

Critical thinking ability

Exceptional problem-solving skills

Strategic thinking

Flawless written communication

Strong verbal communication

Extreme organization

Attention to detail

Time management

Digital native

Resourcefulness

Tools

Advanced MS Office

Google Workspace

Job description

Position Overview

We\'re seeking an exceptional Executive Assistant to serve as a true business partner and extension of the COO & founder. This is not a traditional administrative role - it\'s an opportunity for a highly capable individual to take ownership of diverse initiatives across personal and professional domains, freeing up executive time for strategic focus. The ideal candidate thrives in ambiguity, tackles unfamiliar challenges with confidence, and operates with the judgment and autonomy of a business owner.

Critical distinction : We need someone who can think strategically and make intelligent decisions independently, not just execute tasks. You should be comfortable analyzing situations, evaluating options, and choosing the best path forward without constant guidance.

Example Projects & Responsibilities

Business Operations

• Manage complete vendor lifecycle : research, RFP processes, quote comparison, negotiation, and hiring coordination for services (contractors, maintenance, professional services)
• Own basic financial operations : accounts payable / receivable, billing cycles, invoice processing, payment scheduling
• Serve as primary liaison with bookkeeper, accountants, and financial advisors - ensuring accurate, timely financial records
• Coordinate with legal counsel on contracts, agreements, and misc. compliance matters
• Manage insurance renewals, policy reviews, and claims processing
• Handle business licensing, permits, and regulatory compliance tracking

Project Management

• Lead cross-functional initiatives from conception to completion without hand-holding
• Create and maintain project documentation, timelines, and stakeholder communication
• Conduct first-pass quality reviews on all external deliverables (marketing materials, vendor work, consultant reports)
• Research and implement new business processes and systems
• Manage office or facility improvements

Strategic Support

• Draft initial versions of important communications, proposals, and strategic documents
• Attend meetings as principal\'s proxy when appropriate
• Make decisions within defined parameters without seeking approval
• Identify and pursue new business opportunities or cost-saving initiatives

Administrative Excellence

• Manage email - draft responses, flag priorities, handle routine correspondence independently
• Build and maintain systems for email triage, task tracking, and follow-up to ensure nothing falls through the cracks
• Field and resolve staff requests, escalating only when necessary
• Maintain confidential files and sensitive information
• Process expense reports and reimbursements

Ad Hoc Problem Solving

• Navigate complex bureaucratic processes (immigration, licensing, permits)
• Research and solve novel problems with no template or precedent
• Interface with professionals (lawyers, accountants, doctors) on principal\'s behalf

Mandatory Requirements

Intellectual Capability

• Critical thinking ability : Must be able to analyze complex situations, identify key issues, and develop strategic solutions - not just follow instructions
• Independent decision-making : Comfortable making judgment calls and defending reasoning behind decisions
• Exceptional problem-solving skills : Must independently research and solve complex, unfamiliar problems without guidance
• Strategic thinking : Ability to see the bigger picture and make decisions aligned with long-term objectives
• Fast learner : Proven ability to quickly master new domains, industries, and skill sets
• High cognitive flexibility : Comfortable switching between vastly different types of tasks and thinking modes
• Analytical mindset : Ability to break down complex problems, identify root causes, and propose multiple solution paths

Communication Excellence

• Flawless written communication : Professional business writing, clear documentation, error-free correspondence
• Strong verbal communication : Articulate phone presence, ability to represent principal in meetings
• Stakeholder management : Skilled at managing down and across organizations

Operational Excellence

• Extreme organization : Proven systems for managing multiple complex projects simultaneously
• Attention to detail : Error-free execution in financial matters, contracts, or communications
• Time management : Ability to prioritize and meet deadlines without supervision
• Documentation skills : Creates clear processes and maintains comprehensive records

Technology Proficiency

• Digital native : Intuitive understanding of modern software tools and platforms
• AI integration : Regular and effective use of AI tools (ChatGPT, Claude, etc.) to enhance productivity
• Quick adoption : Ability to learn new software / platforms within hours, not days
• Automation mindset : Constantly seeks ways to systematize and automate recurring tasks
• Advanced MS Office / Google Workspace : Expert-level proficiency required

Professional Attributes

• Extreme ownership mentality : Takes full responsibility for outcomes
• Proactive approach : Anticipates needs, identifies problems before they occur
• Confidentiality : Impeccable judgment handling sensitive personal and business information
• Resourcefulness : Finds creative solutions with limited resources or information
• Intellectual curiosity : Genuinely interested in understanding the "why" behind tasks, not just the "what"

Work Style Requirements

• Time zone alignment : Must be available during CST / EST business hours
• Flexibility : Willing to occasionally handle urgent matters outside standard hours
• Remote work capability : Fully equipped home office with reliable, stable and fast internet (100+mb / s)
• Long-term commitment : We are seeking to build a long-term, lasting relationship

Character Requirements

• Integrity : Unquestionable ethics and honesty in all dealings
• Discretion : Mature judgment about what to share, when, and with whom
• Initiative : Self-starter who doesn\'t wait for instructions
• Adaptability : Thrives in changing environments and unclear situations
• Resilience : Bounces back quickly from setbacks or course corrections
• Humility : Willing to tackle any task, no matter how small or unglamorous
• Intellectual confidence : Comfortable challenging ideas respectfully and proposing better alternatives

What Sets This Role Apart

• Think like an owner : Make decisions as if it were your own business
• Connect dots : See relationships between seemingly unrelated tasks and optimize accordingly
• Question intelligently : Know when to push back on requests that don\'t make sense
• Improve continuously : Constantly refine processes and suggest better ways of doing things
• Balance autonomy with alignment : Know when to act independently vs. when to seek input

Compensation & Benefits

• Salary ranging from USD $2,000 to $3,500 / month
• This is a fully remote position

Application Requirements

• Detailed cover letter explaining why you\'re uniquely suited for this role
• Resume highlighting relevant experience managing complex, diverse responsibilities
• Three professional references who can speak to your ability to work autonomously and effectively

We\'re looking for someone who reads this description and thinks "This is exactly what I\'ve been looking for" rather than feeling overwhelmed. If you\'re energized by variety, complexity, and the opportunity to have massive impact, we want to hear from you.

Final note: If you\'re someone who prefers clear task lists and detailed instructions, this role isn\'t for you. We need a true thinking partner who can navigate ambiguity and create structure where none exists.