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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