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:- 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
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What you Bring:- 3+ years of experience in tech/product roles with strong execution ownership
>- 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.
- 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, 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
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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.
