Administrative Assistant

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

As the Administrative Assistant to the executive leadership team at Caseware, you’ll be instrumental in supporting our Executive Leadership, ensuring the smooth operation of the executive’s daily responsibilities, serving as a trusted partner in managing general administration, schedules and communications.

You will primarily support executives across Go-To-Market functions (Sales, Marketing, Customer Success) and People Operations, helping drive coordination, efficiency, and alignment across these critical areas of the business.

❗This is a existing vacancy

❗ In this role, you will be reporting directly to the Chief People Officer, while working closely with the Executive support team supporting the full Executive leadership team.

❗ This role is hybrid, in office at least three days a week, and is open to Greater Toronto Area residents. This role may require business travel, as needed.

What you'll be doing

• Provide administrative support to members of the executive team, with primary support for the Chief Commercial Officer, Chief Customer Success Officer, Chief Marketing Officer and Chief People Officer; provide backup support to the broader Executive Leadership Team administrative group, as needed.

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Manage executive calendars and coordinate travel arrangements, ensure optimal time allocation , prioritization, and meeting preparation. Apply critical thinking to validate and refine AI-generated outputs used in communications, scheduling, and reporting.

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Create, submit and track expense reports, manage corporate credit cards, and ensure organized and timely reimbursement processes .

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Maintain and organize files, records, and documentation for easy access and retrieval.

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Coordinate departmental events, team offsites as directed, in alignment with the office facilities team s .

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Support leadership meetings, as directed, by coordinating invitation, office and/or virtuated meeting needs.

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Partner with the broader administrative team and Executive Assistant to the CEO on ad hoc projects, events, and travel coordination.

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Operate with an AI-first mindset, leveraging tools to enhance productivity, scheduling efficiency, and decision-making.

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Integrate AI into administrative workflows to improve efficiency, scalability, and overall outcomes. Identify opportunities to streamline processes and enhance executive support through AI-enabled solutions.

What you will bring

• 0-2+ years of experience supporting executives and/or sr. Leaders in large, global organizations

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• Experience supporting multiple stakeholders and demonstrated ability to
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• Anticipate leadership needs and proactively offer solutions and/or support.
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• Experience with maintaining complete confidentiality, discretion and trustworthiness
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• Highly organized and detail-oriented, with attention paid to follow through and able to prioritize with minimal oversight
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• Strong scheduling and travel coordination experience
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• Proficiency with Microsoft suite of office applications (Word, Docs, Sheets, Excel, etc) and openness to adopting new technologies, including AI-enabled tools.
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• Positive, solution oriented and effective communication and collaboration with stakeholders at all levels of an organization