Back to Jobs

Senior Technical Program Manager - Product Organization

Remote, USA Full-time Posted 2026-06-16

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!

    • Additional Information

    About Caseware

    Caseware’s cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams continuously collaborate, innovate, and build upon our existing suite of products. With a customer-focused mindset, we are shaping the future of audits, financial reporting, and financial data analytics.

    With a strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase, doubling down on the people and products that have made us successful.

    One of our core values is Many Voices, One Team, and we are dedicated to building diverse, equitable, and inclusive teams that reflect our global customers. We welcome candidates of all backgrounds to apply.

    If you require accommodations or have any questions during the application process, please contact our People Operations team at [email protected].

    Any candidates receiving an offer will need to successfully complete a background check through Certn.co, including an Identity Verification and Criminal Record Check. Executives and Senior Managers may also undergo a Soft Credit Check.

    apply to this job
    Apply Now

    Similar Jobs

    Staff Security Engineer (IAM), Remote

    Remote, USA Full-time

    Market Manager, Florida

    Remote, USA Full-time

    Risk Performance Data Analyst, Remote

    Remote, USA Full-time

    Clinical Risk Educator, Remote

    Remote, USA Full-time

    Program Manager- Climate Resilience and Disaster Preparedness

    Remote, USA Full-time

    Community Health Worker, Bilingual in Spanish

    Remote, USA Full-time

    Member of Technical Staff, Transparency

    Remote, USA Full-time

    Strategic Account Executive, Enterprise

    Remote, USA Full-time

    Member of Compliance, Regulatory Relations

    Remote, USA Full-time

    Lead, Trading & Brokerage Compliance

    Remote, USA Full-time

    Bookkeeper Staff Accountant

    Remote, USA Full-time

    Urgently Require Flexologist: personal trainers, PTAs, massage therapists, and dance/yoga/Pilates Instructors in Portland, OR

    Remote, USA Full-time

    Digital Experience Marketing Manager job at UPS - United Parcel Service in Alpharetta, GA

    Remote, USA Full-time

    Experienced Customer Support Representative – Entry-Level Remote Chat Agent Position

    Remote, USA Full-time

    (Remote Jobs No Experience) Amazon Customer Service Jobs ? Apply Now

    Remote, USA Full-time

    Experienced Full Stack Data Entry and Performance Analysis Specialist – Flight Operations and Customer Experience

    Remote, USA Full-time

    Experienced Full Stack Chat Support Manager – Work from Home – arenaflex

    Remote, USA Full-time

    Online Order Filling Team Associate

    Remote, USA Full-time

    Senior Electrical & MEP Design Consultant

    Remote, USA Full-time

    Experienced Data Entry and Customer Support Agent – Remote Opportunity with arenaflex

    Remote, USA Full-time