Head of Canadian Solutions

Caseware combines over 35 years of industry expertise with AI-powered technology to transform how audit and accounting professionals work. Serving organizations across 130 countries, we bring intelligent automation directly into audit and financial reporting workflows—helping professionals reduce manual work, navigate complexity, and focus on informed decisions. Join our global team and help build technology that strengthens trust in financial information.

As the Head of Canadian Solutions at Caseware, you will drive the product vision, strategy, and roadmap for our Canadian audit, assurance, and financial reporting products. You will lead, develop, and grow a team of product managers, and be the person accountable for what Caseware builds for the Canadian market and why.

You will decide what should be built and for whom, size the opportunity behind it, and set the priorities the roadmap runs to. You will be the internal expert on the Canadian profession and the external face of Caseware to it.

You’ll be reporting into:

VP, Product — Enterprise Solutions & Ecosystem

❗ CPA (Canada) in good standing is a hard requirement.

❗ Candidates must be eligible to work in Canada. This role will require some travel.

❗ This is a full-time permanent position

❗ This is a new vacancy

📍 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 Suite 1100 Toronto ON.

What you will be doing:

Strategy and roadmap

Own the product vision, strategy, and roadmap for Canadian audit, assurance, and financial reporting solutions.

Define what should be built for the Canadian market, for whom, and the opportunity it addresses.

Ensure the Canadian roadmap aligns with the overall product and company vision.

Own prioritization, scoping, and planning for the Canadian portfolio, and identify and mitigate delivery risks against the roadmap.

Decide what enters the portfolio and what is retired and produce the business case behind each decision.

Make the build, buy, or partner recommendation for Canadian capability gaps.

Report Canadian portfolio performance to senior leadership.

Market and customers

Be an expert on the Canadian public accounting domain, the market, and the trends shaping it.

Keep Canadian solutions current with CPA Canada standards, including CAS, ASPE, ASNPO, and IFRS as adopted in Canada, and interpret changes before they land.

Be the champion and voice of the customer, and build lasting relationships with Canadian firms.

Feed what you learn from customers back into the roadmap.

Represent Caseware to the Canadian profession, including standard-setters, firm advisory groups, and industry bodies.

Quality and compliance

Hold quality as a top priority, and treat standards compliance as a deliverable rather than an assumption.

Set the bar a Canadian solution must meet before it ships.

Go-to-market and commercial

Work with go-to-market teams on positioning, launch, enablement, and the success of Canadian solutions in market.

Contribute the product view to commercial strategy, pricing, and packaging for the Canadian portfolio.

Team and leadership

Lead, hire, and develop the product management team, and grow it as the portfolio grows.

Set the strategy out clearly and often, so everyone working on Canadian solutions understands where it is going and why.

What you will bring:

A CPA (Canada) in good standing, with a strong interest in technology.

Actively practiced within the last ten years.

Deep knowledge of current Canadian audit and accounting standards, and the ability to read and interpret future standards.

10+ years of public accounting experience, or combined public accounting and product management experience

Experience leading and growing teams.

Experience working with sales, customer success, and marketing teams on pipeline, go-to-market, and retention.

Experience prioritizing and planning across competing demands and surfacing risk early rather than late.

Able to set out a strategy and the evidence behind it to a senior audience.

A lifelong learner, self-motivated to stay current with professional standards and changes in the accounting and auditing profession.

Results orientated — willing to roll up their sleeves and take initiative.

A self-starter who works effectively without daily supervision and communicates clearly with colleagues across regions.

Salary Range:

The annual base salary for this position is between $175,000 CAD and $195,000 CAD per year.

This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically.

What's in it for you:

Shape what’s next with AI: Help transform audit and accounting through AI-powered technology. Explore new ways to bring AI into our own workflows, rethink how work gets done, and turn ideas into meaningful improvements for our teams and customers.

Make an impact that matters: Contribute to solutions that help professionals navigate complexity, make informed decisions, and strengthen trust in financial information around the world.

Bring your voice. Expand your perspective: Collaborate with a diverse global team where your ideas are valued, knowledge is shared, and different perspectives lead to better outcomes.

Build a career that grows with you: Develop your skills, take on new challenges, and explore career opportunities as our business and technology evolve.

Thrive at work and beyond: Enjoy competitive compensation, comprehensive benefits, recognition programs, and performance bonuses, alongside flexible work options, remote opportunities, and generous time off.

Many Voices, One Team:

We’re committed to building teams as diverse as our customers through equitable and inclusive hiring. We welcome candidates of all backgrounds. If you need accommodations or have questions at any stage of the application or interview process, contact our People Operations team at [email protected].

Background Check:

All successful candidates will undergo background screening, which may include identity verification, criminal record checks, and/or reference checks, as appropriate to the role and location and in accordance with applicable law.

Security and Fraud:

All employees are expected to apply security best practices and work within secure handling guidelines to perform assigned responsibilities when accessing data and business information.

Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.com and our open positions are always listed on reputable job boards and on our website https://jobs.lever.co/caseware. We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.