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 fast. You’ll thrive if you’re a self‑learner, highly adaptable, and take extreme ownership, especially in ambiguous, fast‑moving environments.

Location: Hybrid role – 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, 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 0→1 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, quick‑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. This role is also eligible for discretionary bonus and/or commission, as well as other benefits.

Benefits

Innovation is at our core – we work with cutting‑edge technology in accounting and financial reporting

Collaborative culture – your ideas are valued and knowledge sharing is encouraged within a supportive, inclusive team

Work‑life balance – flexible work options, remote opportunities, and generous time‑off policies

Competitive compensation – including health insurance and retirement plans

Impactful work – your contributions directly affect how our clients manage financial processes

Recognition and rewards – performance bonuses and opportunities for career growth

Global opportunities – work on international projects with a diverse team

We welcome and encourage candidates of all backgrounds. If you require accommodations or have any questions during the application or interview process, please contact our People Operations team.

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📌 Product Manager, Growth (Ontario)
🏢 Medium
📍 Ontario