Senior Product Manager, AI-Powered Workflows

Own the product lifecycle end to end, from customer discovery and opportunity assessment to roadmap development, prioritization, launch, and iteration.

Lead discovery activities with contractors and small business owners to understand their needs, workflows, and challenges, translating insights into intuitive product experiences.

Design and deliver AI-powered assistance and workflow automation across essential business activities, including jobs, invoicing, scheduling, customer communications, and payments.

Explore opportunities to connect AI-enabled chat and voice interactions with practical actions that help users complete their daily tasks.

Evaluate where AI can genuinely improve the user experience and where traditional product solutions are more effective.

Design AI-powered experiences that prioritize transparency, user control, reliability, and effective recovery when automation does not perform as expected.

Partner with Engineering, Design, and AI/platform teams to manage technical dependencies, integration opportunities, product quality, and implementation trade-offs.

Develop prototypes and run experiments to validate assumptions, gather feedback, and accelerate product learning.

Monitor customer feedback, usage analytics, and success metrics to improve adoption, effectiveness, and user trust.

Communicate product decisions, priorities, and trade-offs clearly while aligning stakeholders and driving execution in a dynamic environment.

5–7+ years of product management experience, preferably in B2B SaaS, SMB SaaS, or complex workflow-based products.

A proven track record of owning products or significant product capabilities from initial discovery through launch and continuous iteration, with measurable results.

Practical experience shaping or delivering AI-powered product features and workflows, with a clear understanding of their user value, limitations, and reliability considerations.

Strong capabilities in customer discovery, product design, roadmap planning, prioritization, analytics, and experimentation.

Excellent collaboration and communication skills, with the ability to work effectively across Engineering, Design, and technical teams.

Strong product judgment and the ability to balance customer needs, business objectives, technical constraints, and execution priorities.

An adaptable and accountable approach to working in evolving environments.

An AI-native approach to product development, including hands-on use of AI tools for research, prototyping, testing, and improving personal workflows.

Experience with conversational AI, AI agents, integrations, or human-in-the-loop workflow design.

Familiarity with product-led growth strategies.

Experience in field service management, construction, skilled trades, or other small-business service industries.

Competitive compensation: Annual target base salary of CAD $150,000–$175,000, depending on location, local market conditions, experience, and expertise.

Flexible working arrangements: Choose between remote, hybrid, or in-office work within Canada.

Flexible time off: Access to a generous flexible time-off (FTO) policy.

Wellness support: Comprehensive wellness benefits, including an annual wellness stipend.

Retirement savings: Registered Retirement Savings Plan (RRSP) with a 4% company match.

Distributed work environment: Collaborate with an international team across multiple countries and time zones.

Travel opportunities: Occasional travel to the Toronto office, ideally once per quarter, with potential travel to headquarters in Denver or other North American offices.