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About the role
- Manager advancing strategic programs and AI transformation for Caseware, a global accounting and financial reporting software company. Leading analyses, executive materials, and cross-functional execution.
Responsibilities
- Support the Chief of Staff and Executive Leadership Team in advancing high-priority strategic initiatives across functions, regions, and business units
- Lead data-driven analyses, business cases, and scenario modelling for strategic priorities, investment decisions, and resource allocation
- 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 to accelerate research, analysis, synthesis, reporting, and program execution
- Identify opportunities to improve how the broader organization operates
- Develop 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 and surface risks, interdependencies, and decisions requiring executive attention
- Conduct 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 strategy 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
- 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
- Experience developing polished, executive- and board-ready materials
- Experience using AI tools to accelerate research, analysis, synthesis, and content development
- Strong judgment to validate AI outputs
- Advanced proficiency in Excel and PowerPoint
- Familiarity with SQL and Tableau is an asset
- Highly resourceful, organized, and adaptable
- Professional maturity and discretion to manage multiple priorities and confidential matters in a fast-paced environment
Benefits
- Flexible work options
- Remote opportunities
- Generous time-off policies
- Health insurance
- Retirement plans
- Performance bonuses
- Recognition programs
- Opportunities for career growth
- International projects
- Collaboration with a diverse, global team
- Executive exposure to the CEO, Chief of Staff, and execution leadership team
- Accelerated learning and growth
- Professional development through strategy, analytics, executive communication, and program leadership experience
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