Executive Assistant to CEO

JumpFactor is an Award-winning 7-time Growth 500 Fastest Growing Agency in Canada. We are currently looking for an experienced and highly organized Executive Assistant to support our CEO.

Role Overview :

The Executive Assistant will be a key partner to our CEO , ensuring smooth execution of executive tasks and projects. The ideal candidate will have 3–7 years of experience demonstrating exceptionally strong organizational, communication, and problem-solving skills while supporting 1-2 executives .

You are proactive and driven , in line with our core value of tenacity . You will act as a primary liaison for internal and external matters, and also support strategic initiatives. The objective is to keep the CEO highly productive in his zone of highest value, while guarding his time and eliminating anything that can be taken off his plate.

The company is looking to grow 5X in size in the coming 4 years. This is an extremely fast-paced environment, which provides for rapid growth opportunities. As the role evolves, you'll have the opportunity to advance into a Senior / Director-level position within 2-3 years of a strong track record in the role, where you'll delegate executive assistant duties to junior assistant(s), allowing you to take on more strategic responsibilities and mentor team member(s).

Jumpfactor's Core Values :

Be STRATEGIC

Be PASSIONATE

Be TENACIOUS

Prioritize LEARNING

Embrace TEAM

Maintain INTEGRITY

Qualifications :

3-5+ years of executive assistant experience, supporting 1-2 CEOs / C-level executives.

Experience in project management.

Extremely resourceful with ability to find or learn rapidly

Keen interest or understanding of management, finance, and investments

Exceptional verbal communication and negotiation skills

Experience coordinating with lawyers and managing legal matters.

Hyper-diligent with organization and task management

Knowledge of developing and implementing company policies and procedures.

Event planning and execution skills.

Proficient in calendar management and email management.

Experience in handling personal matters for executives.

Proficiency in cloud applications and Google Workspace

Very comfortable and fast with technology applications

Resident in Canada with a valid driver's license.

MBA or equivalent education is preferred.

Soft Skills :

Constant follow-up and proactive approach to executive support.

Strong problem-solving and critical-thinking abilities.

High level of discretion and confidentiality.

Excellent time management and organizational skills.

Articulate, business-focused, and well-spoken.

Strong organizational and multitasking skills.

Excellent verbal and written communication skills.

Very driven and tenacious

Flexibility to work with the CEO’s outside of normal business hours

Key Responsibilities :

Executive Support :

Initiate personal and business tasks and projects proactively in line with goals

Attend all meetings required with CEO to ensure decisions are actioned before and after

Consistent follow through to close out tasks and projects ensuring momentum

Coordinate internal and external communications, ensuring timely responses and follow-ups.

Identifying and prioritizing critical tasks, events and driving things forward independently with a cadence of input from the CEO largely driven by yourself

Assist in creation and rollout of playbooks and procedures with input from Executives

Provide daily support to the CEO, including calendar & email management

Managed cadences to extract decisions from CEO, owned and driven by you

Oversee various business and personal investments and affairs as required

Stakeholder Management / Representation :

Step in on behalf of the CEO for internal and external meetings as needed.

Assist in management and coordination with direct reports of the CEO

Ensure a consistent flow of KPIs and data / metrics visibility for the CEO

Adhere and execute closely in line with the principles of EOS Traction

Embody and champion the core values alongside the CEO to the company / team

Identify and solve operational issues alongside the CEO.

Audit for adherence to process and KPIs as required for executive visibility

Research, Vendor Coordination, and Legal Management :

Conduct research using calls, online searches, and networks to solve business challenges.

Leverage relationships and resourcefulness to identify solutions.

Analyze options and recommend or make decisions with and without CEOs input

Manage vendor and consultant relationships and affiliations.

Coordinate with legal teams on contract reviews, revisions, and compliance.

Oversee all contract management, including handling redlines with lawyers.

Negotiate terms and pricing with vendors, consultants, and contractors

Next Steps : If you are excited about this opportunity and meet the qualifications, we invite you to apply. Successful candidates will undergo a series of assessments to further evaluate their potential.

Job Type : Full-time, Remote (This is a remote position with occasional / rare local errands.)

What does our ideal candidate look like?

• Highly resourceful and action-oriented : Takes initiative, finds solutions quickly, and drives tasks to completion independently.
• Experience in high-growth environments : Proven track record in small-to-mid-sized companies (20-500 employees) with a focus on scalability and efficiency. Experience in SaaS or digital industries is a significant asset.
• Business-savvy and adaptable : Understands business operations and can contribute strategically. Nonprofit, government, or overly corporate backgrounds are not ideal—this role requires flexibility, innovation, and speed.
• Intermediate-level with hunger to grow :  Ideal candidates have a growth mindset, are open to new processes, and thrive in a fast-paced environment.
• Executive-level ownership : Has worked directly with 1-2 executives, managing their entire task lists and ensuring decisions are executed seamlessly. This includes stepping into meetings on behalf of the CEO when necessary.
• Tech-savvy and fast learner : Comfortable and quick with technology, cloud platforms, and business tools. Needs to learn and adapt to new systems rapidly.
• Legal and stakeholder management : Skilled in reviewing contracts, managing vendor negotiations, and coordinating with lawyers on complex matters.
• Hyper-organized and relentless : Handles competing priorities without dropping the ball. Organization is not optional—this role demands someone who thrives on meticulous detail and follow-through.
• Proactive communicator : Strong verbal and written communication skills, with the ability to manage relationships at all levels. Must be comfortable negotiating, representing the CEO, and addressing challenges head-on.
• Drives results and accountability : Takes ownership of projects, follows up aggressively with stakeholders (including the CEO), and ensures momentum is maintained.
• Remote-focused : No need for experience in event planning, itinerary management, or travel coordination. This role is entirely remote and requires someone who can excel without a physical office environment.

If this aligns with your expertise and what you’re looking for in your next opportunity, we encourage you to apply!