Senior AI Product Manager for LLM-Powered Workflows

Jobtailor; Toronto; On-site; CAD 120,000 - 170,000; Full time

Job summary

Jobtailor in Toronto is seeking a senior Product Manager to own the Scout product roadmap, direction, sequencing, and alignment with company objectives. You will define analyst workflows end-to-end across modeling, comps, and research; write actionable specifications; and collaborate daily with engineering and design to drive AI-driven product decisions.

You will evaluate AI output quality, conduct expert-user discovery, and enable sales and customer success with strong product context while

Qualifications

• 5+ years of product management experience.
• Owned an AI product or complex workflow product end-to-end as the owner.
• Experience shipping LLM-powered products.
• Ability to explain problems and changes involving evals, tool design, retrieval, or prompting.
• Close collaboration with engineers and understanding of implementation tradeoffs.
• Experience partnering with designers through disagreement and making UX decisions.
• Comfortable conducting discovery with expert users and changing the roadmap based on research.
• Experience building for expert users in a technical domain.
• Direct exposure to financial workflows, Excel-native products, or data-heavy tools is a strong plus.
• Clear writing and direct communication.
• Experience in a startup or early-stage environment.
• Daily use of AI tools.
• Ability to work in Toronto, Canada.

Responsibilities

• Own the Scout product roadmap, direction, sequencing, and alignment with company objectives.
• Define analyst workflows end-to-end across modeling, comps, and research.
• Work directly with engineering and design daily.
• Write actionable specifications and participate in technical design discussions.
• Make real-time product decisions as new constraints emerge.
• Drive repeat usage and durable retention around the quarterly earnings cycle.
• Define healthy engagement metrics, instrument the product, and increase repeat behavior.
• Evaluate AI output quality through evaluation frameworks and accuracy and confidence standards.
• Conduct analyst discovery through user interviews and workflow observation.
• Enable sales and customer success teams with product context.
• Stay close to the field and identify product issues.
• Prototype and pressure-test ideas using AI tools.
• Validate or reject hypotheses with customers before consuming engineering resources.

Skills

Product Roadmap Development

Analyst Workflow Definition

Specification Writing

AI Tool Prototyping

Data Analysis

User Interviewing

Evaluation Frameworks

UX Decision Making

Technical Design Discussions

Engagement Metrics Definition

Tools

AI Tools

Excel

Data-Heavy Tools

Job description

Jobtailor in Toronto is seeking a senior Product Manager to own the Scout product roadmap, direction, sequencing, and alignment with company objectives. You will define analyst workflows end-to-end across modeling, comps, and research; write actionable specifications; and collaborate daily with engineering and design to drive AI-driven product decisions.

You will evaluate AI output quality, conduct expert-user discovery, and enable sales and customer success with strong product context while