Director, Strategic Programs (Contract)

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 (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn 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

📍 Location: 
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.