Director, Strategic Programs

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 over 36,000 accounting and audit professionals list Caseware as a skill on their Linked In profiles!

Caseware is seeking a Director, Strategic Programs (Contract) to join the Office of the CEO for a 12-18 month mandate. This is a senior, high-impact role designed for a strategy professional with 7-10 years of experience who is ready to operate inside the business and drive tangible enterprise value creation.

You will work directly with the Chief of Staff and broader Executive Leadership Team (ELT) to design and execute critical elements of Caseware’s transformation agenda. This role sits at the center of enterprise-wide strategic priorities and will focus on identifying, shaping, and delivering initiatives that accelerate growth, improve revenue quality, and enhance operational performance.

This is not a purely advisory role. The mandate is intentionally split:

Phase 1:
Strategic Design — Frame the problem, conduct rigorous analysis, and define the path forward

Phase 2:
Operational Execution — Partner cross-functionally to implement initiatives and ensure measurable impact

You will operate as a senior individual contributor, with significant autonomy and executive exposure.

This is a New Role

This is a 12-month contract, full‑time permanent position

This is a hybrid role requiring the successful candidate to work 3 days a week in our Toronto office located at 351 King St E, Toronto, ON .

• Lead high-priority, cross-functional initiatives tied to Caseware’s enterprise transformation agenda
• Execute and support strategic initiatives under the direction of the Chief of Staff, including analysis, synthesis, and preparation of materials for ELT
• Drive structured, hypothesis‑led problem solving across growth, efficiency, and operating model evolution
• Build robust business cases and financial models to inform executive trade‑offs and investment decisions in alignment with defined operational processes
• Develop executive- and board‑ready materials that clearly articulate strategy, risks, trade‑offs, and expected impact
• Stand up and manage PMO discipline across select enterprise programs, bringing rigor, transparency, and accountability
• Track progress against defined KPIs, identify risks and interdependencies, and drive resolution with initiative owners
• Partner across Finance, R&D, Sales, Marketing, Rev Ops, Customer Success, and People to ensure alignment and execution pace

• 7+ years of experience in Management Consulting, Corporate Strategy, Private Equity portfolio operations, 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
• Demonstrated ability to move from strategic design to hands‑on, cross‑functional execution
• Highly resourceful, adaptable, and capable of navigating ambiguity
• Excellent written and verbal communication skills, with the ability to distill complex issues into clear messages
• Ability to produce polished executive-ready deliverables
• High degree of discretion, professionalism, and ownership

• Executive Exposure:
  Partner closely with the CEO and Chief of Staff and gain 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 SaaS environment
• Meaningful Mission:
  Help transform how auditors and financial professionals work—through modern, data‑driven software that makes a difference

• Innovation is at our core. We work with cutting‑edge technology in accounting…