Director of Strategic Programs

Toronto, Canada /
Executive – Executive /
Full Time - Permanent
/ Hybrid
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!

As CaseWare continues to grow and evolve, so do the needs of our Executive team.

We’re looking to hire a Director of Strategic Programs (DSP) to work directly with our new CEO Dave Osborne and join the Executive Team as a trusted strategic advisor. You'll work across the entire business, promoting collaboration and communication between executives and teams with a focus on ensuring the quality and timeliness of the team’s execution and the strategic roadmap by removing bottlenecks and empowering decisions and projects. 

Key Priority
Your key priority is to project manage all key initiatives such as our Value Creation Plan, all M&A integration plans, BoD level meetings, and other AdHoc initiatives.

❗Please note, that this role is hybrid. The successful candidate will be working from the office 3 days a week - Tue/Wed/Th. The head office is located at 351 King St E., Toronto, ON

In this role, you will be reporting to:
David Osborne - CEO

Talent Partner overseeing the role:
Chengeer Lee - Senior Talent Acquisition Partner

What you will be doing:

    • Act as an extension of our CEO while working closely with the leadership team to ensure priorities are optimized and operational targets are being met
    • Manage and communicate M&A integration status and progress to the ELT on a regular basis
    • Manage the company’s Value Creation Plan (initiatives tied to the Strategic Plan)
    • Ensure the milestones and metrics are reported, tracked, and reviewed appropriately
    • Ensure the best practices are being fully utilized and driving the desired outcome
    • Manage the meeting cadence for the Board of Directors and Leadership Team, ensuring materials are sent in advance, time is well spent, and objectives are achieved
    • Bringing together multiple stakeholders, driving decision-making where appropriate
    • Building and presenting executive presentations for internal and external stakeholders
    • Assess the quality and productivity of processes and suggest ways to streamline operations overall
    • Build trust amongst all the executive leaders and act as advisors on key issues
    • Develop and implement company-specific standard operating procedures and best practices
    • Drive & Manage ad-hoc projects as necessary

What you will bring:

    • Have at least 3-5 years of experience as a management consultant (i.e. Bain, McKinsey, Waterstone, etc.) or relevant work experience
    • Proven Project Management executive experience 
    • M&A, Corporate Development experience, and strong financial modeling skills are considered a strong asset
    • Have 3-5 years within an organization focused on strategy, operations, or finance
    • Have a Bachelor's degree and preference to those who have completed an MBA
    • Have experience working with the executive and board levels of an enterprise software company
    • Have a strong understanding/familiarity with software development or software product road-mapping
    • Are experienced in driving process improvements through successful cross-functional department coordination
    • Have experience managing and leading people, teams, and large groups
    • Are confident in gathering, analyzing, and presenting financial plans and forecasts
    • Are detail oriented and are polished in their business modeling and presentation skills
    • Are able to drive change with or without authority
    • Genuinely align with our core values
About Caseware

Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams are continually collaborating, innovating, and building upon our existing suite of products. With a customer-focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like.

With a recent strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date.

One of Caseware's core values is Many Voices, One Team and with that in mind, we're dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at

Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well.