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Executive Assistant to the Principal / Executive Leadership

Confidential

Ottawa, Ontario permanent

Posted: January 30, 2026

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Quick Summary

An exceptional Executive Assistant—someone who operates as a true force multiplier for executive leadership. This role is for someone that is highly intelligent, impeccably organized, emotionally astute, and always three steps ahead.

Job Description

Executive Assistant to the Principal / Executive Leadership

Location: In-Office (Primary)
Employment Type: Full-Time
Reports To: Principal / Executive Leadership

The Role

We are seeking an exceptional Executive Assistant—someone who operates as a true force multiplier for executive leadership. This role is for someone that is highly intelligent, impeccably organized, emotionally astute, and always three steps ahead.

This is not a traditional administrative role. You will be a strategic partner—anticipating needs before they arise, protecting executive time, and ensuring the organization operates at peak efficiency. You are comfortable in the details and the big picture, and you take pride in going above and beyond.

Our Environment (Important Context)

Our internal culture has a strong startup feel—fast-moving, hands-on, collaborative, and adaptive. However, the caliber of our customers is firmly medium-market to enterprise, and our firm is expected to operate, communicate, and present itself accordingly at all times.

This role is a critical anchor in that balance.

You will help ensure that while we move with startup agility internally, our external presence reflects enterprise-level professionalism, polish, and confidence. From executive communications to meeting readiness and client-facing coordination, this position plays a key role in making sure we consistently “act the part.”

What You’ll Do

Act as a trusted right hand to executive leadership

Proactively manage calendars, priorities, meetings, and deadlines

Anticipate needs, risks, and opportunities—often before they’re articulated

Prepare briefing materials, summaries, presentations, and executive correspondence

Coordinate internal and external stakeholders with professionalism and discretion

Maintain absolute confidentiality on sensitive business and personal matters

Support operational execution—no task is “beneath” you if it moves the business forward

Bring structure, calm, and clarity to fast-moving, high-pressure environments

Leverage technology tools to streamline workflows and improve productivity

Who You Are

You are:

Exceptionally organized, detail-oriented, and reliable

Proactive, intuitive, and comfortable making judgment calls

Confident communicating with executives, partners, and clients

Calm under pressure and adaptable to changing priorities

Comfortable working in-office and being deeply embedded in the business

Someone who takes ownership and pride in excellence

You don’t wait to be told what to do—you see what needs to be done and do it.

Required Qualifications

Bachelor’s degree in Business Administration, Management, or related field

5+ years experience as an Executive Assistant, Chief of Staff, or senior administrative role

Exceptional written and verbal communication skills

Advanced proficiency with modern business tools (Microsoft 365, project management platforms, CRM systems, collaboration tools)

Strong emotional intelligence and interpersonal awareness

Preferred / Bonus Qualifications

Background or coursework in Psychology, Behavioral Science, or Organizational Behavior

Experience supporting founders, executives, or leadership teams in fast-growth environments

Strong instincts for people, timing, and situational awareness

Ability to balance professionalism with warmth and assertiveness

Why This Role Is Different

You will be trusted, empowered, and relied upon

You will have direct exposure to leadership decisions and strategy

Your impact will be felt across the entire organization

This is a long-term, high-trust role for someone who wants to be indispensable

The Right Candidate

This role is for someone who:

Thinks ahead

Moves with confidence

Is unafraid to roll up their sleeves

Holds themselves to an elite standard

Understands that excellence is a mindset, not a job description

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