PURPOSE AND SCOPE

The Director, Product Management is responsible for defining and leading the product technology vision for our client, modernizing its HCM product portfolio. This role combines strategic leadership with technical oversight, driving innovation and guiding the transformation from traditional product practices to a customer-led, market-driven, data-informed, and AI-first operating model.
The role also provides leadership and oversight for Product Operations, ensuring that product management practices, processes, and cross-functional coordination operate efficiently and scale effectively as the organization grows.
 

KEY DELIVERABLES

1. AI-First Product Strategy & Delivery
   • Lead the product vision and roadmap for AI-powered experiences across the HCM portfolio — building agentic layers on top of a proven legacy platform (e.g., AI-assisted payroll data entry, smart time review, intelligent HR workflows, and emerging use cases as they surface).
   • Drive the full AI product development lifecycle: discovery (JTBD, workflow mapping, AI-reimagined workflows), validation (product briefs, prototyping, evaluative interviews), outcome-based road mapping, new product introduction, and post-launch adoption measurement.
   • Design and ship human-in-the-loop AI pipelines with a compliance-first mindset: confidence scoring, validation gates, audit trails, and progressive trust-building with end users.
   • Establish evaluation frameworks for AI output quality including LLM-as-Judge, golden data sets, trace analysis, and continuous accuracy improvement.
   • Ensure accessibility, regulatory compliance (CRA, provincial payroll legislation), and data privacy are embedded into every AI feature from day one.
   • Translate market trends, customer insights, competitive intelligence, and data analytics into actionable product direction — using AI tools to synthesize at speed (e.g., win-loss analysis, support ticket pattern matching, NPS verbatim synthesis).
2. Organizational & Operational Transformation
   • Drive the evolution of the product organization toward customer-focused, market-informed, and outcome- driven practices.
   • Introduce and operationalize modern product management frameworks, including data-informed discovery, experimentation, and continuous learning.
   • Foster a culture that embraces change, innovation, and new ways of working — including the adoption of AI agents and automation tools to improve team efficiency and product quality.
   • Establish scalable product operating models, ensuring consistent product management practices, tools, and workflows across the organization.
3. Design Leadership
   • Lead and empower Product Designers to adopt modern, AI-enabled design practices and tools, encouraging experimentation, rapid iteration, and user-centered outcomes.

• • Ensure Product Managers and Product Designers operate as a unified, high-performing team grounded in customer research, journey mapping, and iterative design methodologies.
  • Champion design excellence, accessibility, and modern user experience standards — including progressive trust design and human-in-the-loop decision points — as core components of product strategy and execution.
  • Inspire the design team to rethink how they work, leveraging AI to enhance creativity and efficiency without sacrificing craft.

1. Data Analytics & Insights
   • Champion the use of data analytics to inform product strategy, prioritization, and performance measurement.
   • Collaborate with Data teams to define key metrics, dashboards, and analytical models that support product decision-making.
   • Ensure product teams consistently use data to validate assumptions, measure outcomes, and refine product direction.
   • Drive adoption as a core PM responsibility: build adoption dashboards, define activation levers, segment accounts by adoption tier, and coordinate digital and high-touch interventions.
2. Product Operations Leadership
   • Provide leadership and strategic direction for Product Operations, ensuring the product organization operates with clear processes, strong cross-functional alignment, and the data needed for effective decision- making.
   • Coach and mentor the Product Operations Manager, including the transformation of product ops with AI tools, workflow automation, and modern operational cadences.
   • Drive standardization of product lifecycle processes: discovery coordination, development handoffs, release planning, feedback loops, and knowledge sharing.
   • Ensure consistent frameworks, templates, and best practices are implemented across the product organization to improve transparency, alignment, and execution.
   • Ensure the product organization has visibility into product performance, release outcomes, and customer feedback trends through dashboards, instrumentation pipelines, and reporting frameworks.
3. Reporting and Analytics
   • Lead and define best practices for client report service requests, applying an AI lens to identify patterns and common themes in customer data needs – to inform the development of a pre-built library of capabilities within the product itself.
   • Apply an AI-first mindset to report design: identify opportunities to automate report generation, build a reusable library of common report patterns, and accelerate custom builds – reducing turnaround time, increasing margin, and progressively shifting the service model toward scalable, product-led delivery.
4. Cross-Functional Leadership & Go-to-Market
   • Build and run cross-functional product pods (Engineering, Design, Sales, Marketing, Support, Implementation, Finance) that own end-to-end product health from discovery through adoption.
   • Partner with Sales and Marketing to translate AI capabilities into competitive positioning, value proposition briefs, launch FAQs, and battle cards.
   • Collaborate with Finance on AI cost modeling, consumption-tier design, and pricing strategy evolution as the organization moves beyond seat-based models.
   • Serve as a senior product voice in strategic planning, roadmap discussions, and cross-functional initiatives — ensuring product decisions balance customer needs, business goals, technical feasibility, and data-driven insights.

1. Talent Leadership & Development
   • Drive organizational change by reshaping teams, roles, and ways of working as product strategy evolves.
   • Actively develop product managers and leaders through coaching, feedback, and deliberate talent planning, creating high-performing teams that can sustain impact through change.
   • Set clear expectations around outcome-driven thinking: every roadmap item traces to a measurable outcome and every launch ships with the telemetry to prove it worked.
   • Drive adoption of structured frameworks across the team: opportunity solution trees, product briefs with business cases, and evaluative interview protocols.
   • Recruit and develop top product, design, and analytics-minded talent to support growth and modernization goals.

JOB QUALIFICATIONS

Required

• • 8-10+ years of product management experience in B2B SaaS environments.
  • Demonstrated track record of shipping AI-powered products in production — not just proofs of concept. You have navigated the messy middle of prompt engineering, context engineering, confidence calibration, and continuous improvement post-launch.
  • Experience building agentic or AI-augmented workflows on top of existing platforms: layering intelligence onto legacy systems while maintaining stability, compliance, and user trust.
  • Deep fluency in the AI product development lifecycle: JTBD, workflow reimagination, AI-powered data analysis, prototype-driven validation, and outcome-based road mapping.
  • Strong UX sensibility and design thinking methodology: understanding of progressive trust design, human- in-the-loop decision points, and confidence-score-driven user interfaces.
  • Proven success transforming product organizations from traditional models to customer-centric, market- driven, and data-informed practices.
  • Experience partnering closely with Product Design to deliver modern, intuitive, and differentiated user experiences.
  • Proven ability to lead teams through significant methodology or tooling changes — not just directing but doing it alongside them and creating the psychological safety to experiment.

Preferred

• • Experience in payroll, HCM, or regulated fintech environments where compliance, audit trails, and data accuracy are non-negotiable.
  • Familiarity with Canadian payroll legislation (CRA reporting, provincial labour standards, ROE, Tax Forms or similar regulatory complexity.
  • Experience in the HCM domain or adjacent enterprise SaaS markets.
  • Experience with product operations: defining operational rhythms, building instrumentation pipelines, and coaching ops practitioners.
  • Exposure to usage-based or consumption-based pricing models and the product instrumentation they require.
  • Track record of working in PE-backed or investor-governed environments where articulating product investment ROI is a regular expectation.