AI Project Manager

Ampliwork, Inc.

$100K — $120K *
Finance & Insurance
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 4+ years in project management or software delivery roles
  • Strong background in financial services like banking or insurance
  • Ability to convert ambiguous client needs into clear plans
  • Proven history of shipping products with multiple stakeholders
  • Excellent communication skills, simplifying complex topics
  • Comfortable in fast-paced, imperfect work environments
  • Demonstrated ownership and decision-making in product delivery.

Responsibilities

  • Lead delivery of AI-powered financial product initiatives end to end
  • Translate client and team needs into clear PRDs and user stories
  • Break down complex problems and maintain team momentum
  • Facilitate client interactions through working sessions and status updates
  • Make informed tradeoffs between speed, quality, and scope
  • Collaborate closely with engineering and design for accurate delivery
  • Quickly learn and adapt to tax and regulatory concepts as needed.

Benefits

  • High ownership and visibility on a critical product
  • Direct exposure to enterprise customers and AI systems
  • Team culture emphasizing clarity, speed, and learning
  • Opportunity to influence AI deployment in regulated financial services
  • Flexible working arrangement with in-person office days.
Full Job Description
The Mission

Own and drive the delivery of a critical AI-powered workflow within financial services, with a focus on tax-related use cases. Your job is not to be a tax expert. Your job is to turn ambiguous client needs into clear requirements, align teams, and get high-quality product work shipped on time.

You will sit at the intersection of Product and Project Management, acting as the execution backbone between customers, engineering, and internal stakeholders.

What You'll Do

  • Lead delivery end to end: Own planning, execution, and tracking for a complex AI product initiative, keeping scope, timelines, and stakeholders aligned.
  • Requirements mastery: Run discovery with clients and internal teams, translate needs into clear PRDs, user stories, and acceptance criteria.
  • Drive execution, not just coordination: Break down complex problems, sequence work, unblock teams, and ensure momentum week over week.
  • Client-facing leadership: Run working sessions, status updates, and milestone reviews with enterprise financial services clients.
  • Product judgment: Make tradeoffs between speed, quality, and scope, with a strong bias toward shipping usable value.
  • Partner closely with Engineering and Design: Clarify intent, answer questions quickly, and keep delivery tight.
  • Learn new domains fast: Absorb tax and regulatory concepts as needed, without letting domain gaps slow execution.


What We're Looking For

Must-haves

  • 4+ years experience in project management, or a hybrid role delivering software products.
  • Strong background in financial services, such as asset management, banking, insurance, or regulated enterprise workflows.
  • Proven ability to gather requirements and turn ambiguity into clear, actionable plans.
  • Track record of shipping complex products with multiple stakeholders.
  • Clear written and verbal communication. You can explain complex topics simply and precisely.
  • Comfort operating in fast-moving, imperfect environments.
  • A product portfolio demonstrating shipped products, delivery ownership, and decision-making. This can include PRDs, roadmaps, case studies, or similar artifacts.


Nice-to-haves

  • Experience working on tax, compliance, or regulatory workflows.
  • Exposure to AI-powered products, automation, or document-heavy systems.
  • Experience working directly with enterprise clients.
  • Familiarity with agile delivery, lightweight roadmapping, and outcome-based planning.


Why You'll Love This Role

  • High ownership and visibility on a mission-critical product.
  • Direct exposure to real enterprise customers and production AI systems.
  • A team that values clarity, speed, and learning over process theater.
  • The chance to shape how AI agents are deployed in regulated financial services.


Required to be in person in the office in Montreal 2 days/week.

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