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! We are seeking a Senior Technical Program Manager to join our Product Organization at Caseware, a leading SaaS organization. As a Senior TPM, you will play a critical role in driving execution, optimizing financial planning, and leading high-impact initiatives that enable our Product and Engineering teams to scale effectively. You will work closely with Product, Engineering, Finance, and Go-To-Market teams to accelerate execution velocity, enhance strategic planning, and optimize resource allocation for maximum impact. 📍 Location: This is a hybrid role requiring the successful candidate to work three (3) days a week in our Toronto office. Contact: Chengeer Lee - Principal Talent Acquisition Partner & Coach What you will be doing:

Work closely with Product and Engineering teams to deeply understand complex product initiatives and inter-team dependencies.

Identify and systematically remove bottlenecks that hinder product delivery.

Drive execution excellence by aligning cross-functional teams, including Product, Engineering, Go-To-Market, and Finance.

Own and optimize the core OPEX financial model for the Product Organization, ensuring data-driven investment decisions.

Analyze trade-offs, assess financial implications, and maximize ROI on product investments.

Develop scenario-based forecasting to enable strategic decision-making for hiring, resource allocation, and infrastructure investments.

Lead high-impact product initiatives that shape Caseware’s trajectory and drive measurable business impact.

Take full ownership of execution, ensuring rigorous tracking, operational efficiency, and high-velocity delivery.

Establish and manage the OKR process for Product and Engineering, tracking progress and driving retrospectives.

Conduct regular 1:1 meetings with the CPO and key stakeholders to enhance visibility and execution alignment.

Improve transparency and accountability within the Product Organization by optimizing process documentation and reporting.

What you will bring

5+ years of experience in Technical Program Management, Strategy, or Chief of Staff roles in a high-growth tech environment.

Background in management consulting (McKinsey, BCG, Bain) or experience in a top-tier tech company (Google, Amazon, Intuit, etc.).

Strong financial modeling, scenario planning, and investment optimization skills.

CPA designation or experience in finance, budget management, or OPEX planning is an asset.

Proven ability to align cross-functional teams and drive execution at scale.

Expertise in Jira, Agile methodologies, and OKR frameworks.

High bias for action, with a strong ability to thrive in ambiguity and deliver results.

Strong stakeholder management skills and ability to influence without authority.

Experience leading and scaling execution in product or engineering organizations.

Ability to operate with extreme ownership and drive high-impact initiatives to completion.

Why this role?

Work directly with the Chief Product Officer to translate strategy into execution at scale.

Play a pivotal role in accelerating product velocity and optimizing financial operations.

Gain exposure to high-impact initiatives that could lead to product leadership, venture capital, or startup leadership roles.

This is an opportunity to own, build, and scale execution in a high-growth product organization. If you’re passionate about driving impact at the intersection of execution, finance, and strategy, we want to hear from you!