Senior Manager, Strategic Programs

Employment Type: Full Time - Permanent Location Type: Hybrid (3 days/week in Toronto office) Salary: Not Specified

Position Overview

Caseware is a leading global Fintech company with over 30 years of experience in the audit and accounting software industry. We serve over 500,000 users across 130 countries and our software is available in 16 languages. This is a high-impact, high-visibility role within the Office of the CEO, reporting directly to the Chief of Staff and working closely with the Executive Leadership Team (ELT). The Senior Manager, Strategic Programs will own critical strategic priorities, including the flagship "Win in the US" initiative. This role requires a blend of strategic thinking, analytical rigor, and cross-functional execution to accelerate enterprise priorities, establish PMO discipline, and drive performance against company objectives. This position is ideal for individuals who thrive in ambiguity, enjoy solving complex problems, and want to operate at the center of strategic decision-making in a global SaaS business.

Responsibilities

• Own and drive cross-functional strategic initiatives, including program management of Caseware’s “Win in the US” priority.
• Act as a thought partner to the Chief of Staff and ELT in designing, tracking, and course-correcting high-impact projects across regions and functions.
• Lead business case development, financial analysis, and market research to support prioritization and investment decisions.
• Establish and manage a lightweight PMO function, bringing rigor, transparency, and accountability to strategic execution.
• Develop high-quality board- and executive-level materials, including initiative updates, KPI dashboards, and performance summaries.
• Track progress against goals, identify risks and interdependencies, and lead resolution planning with initiative owners.
• Collaborate with teams across Finance, R&D, Sales, Marketing, RevOps, Customer Success, and People to embed insights and ensure alignment on strategic direction.
• Conduct ad hoc research and structured problem-solving to support enterprise-level decision making.

Requirements

• Bachelor’s degree in Business, Finance, Economics, or a related field.
• 5+ years of experience in Management Consulting, Corporate Strategy, or a similar strategic or analytical role.
• Strong critical thinking and problem-solving skills, with a strategic mindset and ability to challenge the status quo.
• Proven ability to drive complex, cross-functional programs with senior executive stakeholders.
• Highly resourceful, adaptable, and capable of navigating ambiguity with minimal guidance.
• Experience in financial analysis, investment decision-making, and data-informed strategy work.
• Excellent written and verbal communication skills, with the ability to distill complex issues into clear messages.
• Proficient in Microsoft Excel, PowerPoint, and Word; able to produce polished executive-ready deliverables.
• Experience with primary and secondary research, including data synthesis, is a plus.
• Demonstrated discretion, trustworthiness, and professionalism in handling confidential matters.

Why Join the Office of CEO

• Executive Exposure: Partner closely with the CEO and Chief of Staff, gaining insight into enterprise-level strategy and decision-making.
• Strategic Ownership: Play a lead role in Caseware’s most mission-critical initiatives, from GTM acceleration to operational transformation.
• Learning & Growth: Work alongside high-performing leaders from consulting, finance, and tech, sharpening your skills in strategy, operations, and execution.
• Cross-Functional Impact: Operate at the intersection of Strategy, Finance, R&D, and GTM in a fast-paced, global environment.

Application Instructions

Not Specified.

Company Information

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, Caseware is a recognized leader. Over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles.

Office Location: 351 King Street East, Toronto, Ontario