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’re looking for a high-agency builder-operator to drive execution across product and cross-functional initiatives. This role is focused on turning defined problems into delivered outcomes fast.You’ll thrive here if you’re a self-learner, highly adaptable, and take extreme ownership, especially in ambiguous, fast-moving environments. Many strong fits for this role come from startup or founder-led teams, where they’ve had to figure things out, wear multiple hats, and drive outcomes with minimal structure.
❗This is a full time position.
❗ This is a New role.
📍 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.
What you will be doing:
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Own end-to-end execution of defined product and business initiatives
- Stay ahead of the AI landscape — monitor model developments, new architectures, emerging agent patterns, and competitor moves, and bring a clear point of view on what matters for Caseware
- Define and own product health metrics for AI features: task completion, correction rates, override frequency, trust signals, and time-to-completion — and use them to drive product decisions.
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Break down ambiguous asks into clear plans, milestones, and deliverables
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Drive cross-functional alignment across product, engineering, design, and business teams
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Proactively identify and remove blockers to keep work moving
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Ensure tight follow-through, nothing falls through the cracks
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Track progress and maintain high delivery velocity across multiple workstreams
What you Bring:
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3+ years of experience in tech/product roles with strong execution ownership
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Direct experience building and running eval frameworks for AI products — golden datasets, rubrics, human-in-the-loop validation, and regression tracking across releases.
- Technical fluency in LLMs, RAG, prompt engineering, embeddings, and agentic patterns — enough to have substantive conversations with engineers and know when a product problem is a model problem.
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Strong track record of building and shipping (0→1 projects, internal tools, automations, or similar)
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High ownership mindset—you don’t wait for instructions, you figure things out
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Proven ability to operate in ambiguous, fast-changing environments
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Excellent at structuring chaos into actionable plans
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Strong stakeholder management and cross-functional coordination skills
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Ability to drive outcomes without direct authority
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Experience working closely with founders, senior leadership, or lean teams is a strong signal
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Experience in startups or high-growth environments, operating with limited structure and wearing multiple hats is a strong plus
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A self-learner who can quickly pick up new domains, tools, and contexts
Salary Range:
The annual base salary for this position is between $105,000 CAD and $115,000 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:
▪️Innovation is at our core. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions.
▪️We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team.
▪️Work-life balance is important to us. We offer flexible work options, remote opportunities, and generous time-off policies to ensure a healthy work-life balance.
▪️We offer competitive compensation, including a competitive salary and comprehensive benefits such as health insurance and retirement plans.
▪️We are driven by impactful work. Your contributions directly affect how our clients manage financial processes and drive their success.
▪️Recognition and rewards matter to us. We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth.
▪️We embrace global opportunities. Work on international projects and collaborate with a diverse, global team.
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 talent@caseware.com.
AI Usage:
The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness, transparency, and oversight.
Background Check:
Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through Certn.co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.co
Security and Fraud:
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.
