Product Manager, Growth

CaseWare; Toronto; Hybrid; CAD 105,000 - 115,000; Full time

Benefits offered by this job

Flexible work options

Remote opportunities

Health insurance & retirement plans

Job summary

CaseWare, a leading Canadian fintech company, is seeking a driven builder-operator to execute cross-functional product initiatives from Toronto. The role demands ownership, startup‑level adaptability, and a track record of delivering outcomes in fast-moving environments.

The successful candidate will own AI product evaluation frameworks, monitor AI developments, and collaborate closely with founders and leadership. Hybrid work with 3 days in the Toronto office is required.

Qualifications

• 3+ years of experience in tech/product roles with strong execution ownership.
• Experience building and running evaluation 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.
• Strong track record of building and shipping projects, internal tools, automations, or similar.
• High ownership mindset—you don’t wait for instructions, you figure things out.

Responsibilities

• 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.
• Define and own product health metrics for AI features: task completion, correction rates, override frequency, trust signals, and time-to-completion—use them to drive decisions.
• Break down ambiguous asks into clear plans, milestones, and deliverables.
• Drive cross-functional alignment across product, engineering, design, and business teams.
• Proactively identify and remove blockers to keep work moving.
• Ensure tight follow-through, nothing falls through the cracks.
• Track progress and maintain high delivery velocity across multiple workstreams.

Skills

Product ownership

AI product evaluation frameworks

LLMs & prompt engineering

Cross-functional leadership

Ownership mindset

Ambiguity management

Fast-paced delivery

Stakeholder management

Job description

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 focuses on turning defined problems into delivered outcomes; you’ll thrive 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 at 351 King St E, Toronto, ON.

What you will be doing:

• 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
• Break down ambiguous asks into clear plans, milestones, and deliverables
• Drive cross‑functional alignment across product, engineering, design, and business teams
• Proactively identify and remove blockers to keep work moving
• Ensure tight follow‑through, nothing falls through the cracks
• Track progress and maintain high delivery velocity across multiple workstreams

What you bring:

• 3+ years of experience in tech/product roles with strong execution ownership
• Direct experience building and running evaluation 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
• Strong track record of building and shipping projects, internal tools, automations, or similar
• High ownership mindset—you don’t wait for instructions, you figure things out
• Proven ability to operate in ambiguous, fast‑changing environments
• Excellent at structuring chaos into actionable plans
• Strong stakeholder management and cross‑functional coordination skills
• Ability to drive outcomes without direct authority
• Experience working closely with founders, senior leadership, or lean teams is a strong signal
• Experience in startups or high‑growth environments, operating with limited structure and wearing multiple hats is a strong plus
• 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.

What's in it for you:

• 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 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
• 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