EverPro - Senior Product Manager, AI-Powered Workflows at Joist (Remote CAN)

Role overview

Shape practical AI-assisted product experiences that reduce the administrative load of running a small service business. You’ll own a product area from customer discovery and prioritization through launch and iteration, focusing on workflows such as jobs, scheduling, invoicing, customer communication, and payments. This is a customer-facing product leadership role centered on useful, trustworthy features rather than AI research or model development.

Responsibilities

- Own a product area end to end, setting priorities and a roadmap tied to customer and business outcomes. - Interview contractors and small business owners, then turn their needs into clear product opportunities and coherent workflows. - Design and deliver AI-assisted features and workflow automation from early concept through launch and improvement. - Decide when AI adds value, and design for transparency, user control, and recovery when automation does not work as expected. - Partner with engineering, design, and AI platform teams to manage dependencies, integrations, technical trade-offs, and quality. - Prototype and run experiments, using customer feedback, product data, and success measures to improve adoption and trust. - Explain decisions and trade-offs, align stakeholders, and keep execution moving in an evolving environment.

Requirements

- Five or more years of product management experience, with a strong foundation in B2B SaaS, small-business SaaS, or complex workflow products. - A record of taking products or major features from discovery through launch and iteration, with measurable results. - Practical experience shaping or delivering AI-powered product features or workflows. - Sound judgment about AI’s user value, limitations, and reliability. - Strong customer discovery, product design, prioritization, analytics, and experimentation skills.

Nice to have

Hands-on use of AI tools for research, prototyping, testing, or personal workflows; experience with conversational AI, agents, integrations, or human-in-the-loop design; or familiarity with product-led growth, field service management, construction, trades, or small-business services.

Benefits and work setup

The role can be based anywhere in Canada, remotely, in-office, or hybrid where available. Candidates near Toronto are preferred; otherwise, quarterly visits to the Toronto office are expected. Additional North American travel may be required. Benefits include flexible paid time off, a wellness stipend, and an RRSP with a company match. Target base compensation is CAD $150,000–$175,000 in most locations.