Executive Assistant

Born in the Prairies, now part of a worldwide network, Skip is a tech company with an entrepreneurial spirit and the drive to be the best. We're a people-first, collaborative company with a fun, dynamic and innovative environment. Our vision is to empower everyday convenience. Whether it’s a Friday-night feast, a post-gym poke bowl, grabbing some groceries or sunscreen, our tech platform connects tens of millions of customers with hundreds of thousands of restaurant, grocery and convenience partners across the globe. Ready to make an impact within the Canadian market? This role will support the CEO, VP Operations Strategic Initiatives, and VP Marketing.

The Opportunity

Skip, a fast-growing global technology leader, is hiring an Executive Assistant to support the CEO and other members of the executive leadership team. As Skip continues to scale through product innovation, market expansion, and operational excellence, we need a highly skilled EA who thrives in a fast-paced, dynamic environment and can anticipate challenges before they arise.

The ideal candidate has a proven track record of supporting executives at the highest level. They are proactive, solutions-oriented, and able to navigate complexity with efficiency and discretion. This role goes beyond traditional administrative tasks—it requires critical thinking, strong business acumen, and the ability to drive execution. The successful candidate will provide seamless executive support, ensuring priorities are met, communication flows smoothly, and roadblocks are removed before they impact business operations.

This is an exciting opportunity to make a meaningful impact at one of Canada’s leading technology success stories. If you're a strategic problem-solver who thrives in a collaborative and engaging environment and enjoys turning challenges into opportunities, we’d love to hear from you!

Key Responsibilities

• Strategic Executive Support
• Provide seamless, high-level administrative support to the CEO, including calendar management, travel coordination, and meeting preparation.
• Anticipate needs, solve problems before they arise, and ensure the CEO’s time is optimized for strategic priorities.
• Serve as a gatekeeper, managing communication flow and ensuring key messages are delivered effectively.
• Proactive Problem-Solving Execution
• Identify potential roadblocks and take initiative to resolve issues before they impact business operations.
• Stay ahead of changing priorities, adapting quickly in a fast-moving, dynamic environment.
• Coordinate and follow up on action items from leadership meetings, ensuring execution and accountability.
• Cross-Functional Coordination Relationship Management
• Act as a liaison between the CEO and internal/external stakeholders, fostering strong relationships across the organization.
• Partner with senior leaders to facilitate communication and drive key initiatives forward.
• Ensure the CEO is well-prepared for meetings with relevant materials, insights, and background information.
• Operational Excellence Efficiency
• Enhance processes and implement systems that improve executive team efficiency.
• Maintain discretion and confidentiality in handling sensitive information.
• Manage special projects, initiatives, and research tasks as assigned.
• Event Stakeholder Experience Management
• Lead the planning and execution of high-impact events, including leadership offsites, executive meetings, team gatherings, and external engagements, ensuring seamless logistics and a best-in-class experience.
• Manage executive-level interactions with key stakeholders, ensuring thoughtful touchpoints, timely follow-ups, and a polished, professional experience.
• Oversee personalized gifting and recognition programs for executives, clients, and partners, aligning with company culture and strategic relationships.
  
  

Recipe For Success

• Education Experience – Degree in Business Administration or a related field, with 7+ years of experience in executive support, business management, or project management, ideally in a high-growth technology environment.
• Executive Support Expertise – Proven ability to support senior executives and manage complex priorities.
• Proactive Solutions-Oriented – Anticipates challenges, takes initiative, and ensures smooth execution of tasks.
• Strong Communicator Influencer – Exceptional written and verbal communication skills, with the ability to listen, influence, and collaborate across teams.
• Tech-Savvy Analytical – Proficient in Google Suite including Google Slides with the ability to analyze data and generate insights.
• Highly Organized Adaptable – Versatile, detail-oriented, and dedicated to efficiency, with strong problem-solving skills and a focus on interdepartmental coordination.
• Location – Must be based in Toronto and enthusiastic about collaborating in the office at least three days per week.
  
  

Why work at SKIP?

SKIP is the kind of workplace that garnered a “Top Places to Work in Manitoba” and it was no small coincidence. We set out to make this a place our employees are proud to tell their Mothers, Fathers, friends and anyone who will listen that they work here. SKIP team members feel pride knowing their input and uniqueness are not only embraced but make an impact on a major Canadian company and its satisfied customers. As the company grows, so do you — you meet and surpass new challenges every day.

That’s just a small taste of what it’s like to work at one of Canada’s leading tech companies. If you’re hungry for opportunity, growth, and something meaningful in a dynamic, fun and challenging environment, we’d love to hear from you.

SKIP is proud to be an Equal Opportunity employer. We are committed to fostering a diverse and inclusive environment where all employees feel they truly belong and where everyone is included, seen, heard and respected.

In keeping with our values, all applicants will receive consideration for employment regardless of: gender identity or expression, sexual orientation, race, ancestry, national origin, religion, age, marital/domestic partner status, (dis)ability, neurodivergence, or any other characteristic protected by law. Should you require any accommodations throughout the hiring process, we encourage you to reach out to your talent acquisition specialist.

Note

• All employees will be asked to sign a Consent for Disclosure of Personal Information in order to complete a background check. Job offers will be conditional upon results that the Company determines to be satisfactory.
• This role requires a minimum of three (3) days per week in the office.