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About the Role

This is a high-impact, high-visibility role at the centre of Caseware’s strategic evolution. You will be involved in advancing key strategic initiatives, leading data-driven analyses, and monitoring execution against goals. You’ll combine strong business acumen, analytical horsepower, and structured problem-solving to help design, execute, and track the company’s most important cross-functional efforts.

Responsibilities

Support the Chief of Staff and Executive Leadership Team to advance Caseware’s highest-priority strategic initiatives across functions, regions, and business units.
Lead data-driven analyses, business cases, and scenario modelling to inform strategic priorities, investment decisions, and resource allocation.
Help drive Caseware’s AI transformation by translating enterprise priorities into coordinated, measurable initiatives across Product, R&D, GTM, and corporate functions.
Apply AI-enabled tools and ways of working to accelerate research, analysis, synthesis, reporting, and program execution—while identifying opportunities to improve how the broader organization operates.
Develop clear, executive- and board-ready materials, including strategic recommendations, performance narratives, initiative updates, and KPI dashboards.
Establish structure and accountability across complex, cross-functional programs by defining outcomes, governance, milestones, metrics, and decision points.
Monitor progress against company priorities, proactively surfacing risks, interdependencies, and decisions requiring executive attention.
Conduct targeted market, competitive, financial, and operational research to support executive decision-making.
Partner with leaders across Finance, Product, R&D, Sales, Marketing, Revenue Operations, Customer Success, and People to translate strategic direction into measurable execution.

Requirements

Bachelor’s degree in Business, Finance, Economics, or a related field.
3–6 years of experience in a rigorous analytical environment, such as management consulting, investment banking, corporate strategy, or a comparable strategic role.
Strong analytical and financial acumen, with experience using complex datasets, models, research, and software metrics to inform strategic and investment decisions.
Demonstrated ability to drive complex, cross-functional programs and influence senior stakeholders without direct authority.
Ability to navigate ambiguity, challenge conventional thinking, and translate complex issues into clear recommendations and actionable plans.
Excellent written and verbal communication skills, including experience developing polished, executive- and board-ready materials.
An AI-forward approach to work, with experience using AI tools to accelerate research, analysis, synthesis, and content development—while applying strong judgment to validate outputs and identify opportunities to improve how work gets done.
Advanced proficiency in Excel and PowerPoint; familiarity with data and reporting tools such as SQL and Tableau is an asset.
Highly resourceful, organized, and adaptable, with the professional maturity and discretion to manage multiple priorities and confidential matters in a fast-paced environment.
Candidates successful in obtaining an offer for a position will need to successfully complete a background check through Certn.co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.co

Skills

AI transformation
Data-driven analyses
Business cases
Scenario modelling
Strategic priorities
Investment decisions
Resource allocation
Executive communication
Program leadership
Excel
PowerPoint
SQL
Tableau

Location

Greater Toronto Area (GTA)
Toronto office
Remote

Work Type

Full-time
Permanent
Hybrid

Experience Level

3-6 years

Education Level

Bachelor’s degree in Business, Finance, Economics, or a related field

Salary/Compensations

$125,000 CAD - $145,000 CAD per year

Benefits

Discretionary bonus
Commission
Health insurance
Retirement plans
Flexible work options
Generous time-off policies

About the Company

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.
With a recent strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date.
Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments.
Our teams are continually collaborating, innovating, and building upon our existing suite of products.
With a customer-focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like.

Equal Opportunity

One of Caseware's core values is Many Voices, One Team and with that in mind, we're dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at talent@caseware.com.