Product Manager II, AI-Powered Customer Journey

Are you a dynamic product manager with a passion for impacting small businesses?

Then Jobber might be the place for you! We’re looking for a Product Manager II to be part of our Harbour Foundations team.

This is a remote-first role that can be held in Canada or the United States.

Jobber exists to help people in small businesses be successful. We work with small home service businesses, like your local plumbers, painters, and landscapers, to transform the way service is delivered through technology. With Jobber they can quote, schedule, invoice, and collect payments from their customers while providing an easy and professional customer experience. Running a small business today isn’t like it used to be—the way we consume and deliver service is changing rapidly, technology is evolving, and customers expect more. That’s why we put the power and flexibility in their hands to run their businesses how, where, and when they want! 

Our culture of transparency, inclusivity, collaboration, and innovation has been recognized by Great Place to Work, Canada’s Most Admired Corporate Cultures, and more. Jobber has also been named on the Globe and Mail’s Canada’s Top Growing Companies list, and Deloitte Canada’s Technology Fast 50™, Enterprise Fast 15, and Technology Fast 500™ lists. With an Executive team that has over thirty years of industry experience of leading the way, we’ve come a long way from our first customer in 2011—but we’ve just scratched the surface of what we want to accomplish for our customers.

The team:

The Harbour Foundations team is building the internal foundation for an AI-powered customer journey at Jobber. This team’s mission is to create scalable, intelligent systems that give GTM teams clear, actionable visibility into every AI-driven interaction — enabling more personalized, efficient, and proactive support across the entire customer lifecycle.

As our AI footprint grows across Sales, Success, Support, and Onboarding, Harbour serves as the connective tissue that unifies these interactions, eliminates context gaps, and brings clarity to complex customer journeys. By centralizing fragmented tools and surfacing real-time insight into conversations, sentiment, and customer intent, the Harbour team is redefining how we observe, influence, and improve our AI-human hybrid workflows.

The role: 

Reporting to the Director, Product Management - Growth, the Product Manager II will lead key initiatives within Jobber’s AI-powered internal GTM platform — Harbour. You will play a critical role in shaping how Jobber supports and scales AI-driven customer interactions by building internal tools that give GTM teams visibility, context, and control. Working closely with Engineering, Design, and GTM stakeholders across Success, Support, Sales, Onboarding, and Marketing you will own the roadmap and execution of features that surface key AI insights, unify customer touchpoints, and lay the groundwork for a scalable, role-optimized internal experience.

The Product Manager II will:

• Lead end-to-end product development for Harbour, delivering AI-powered internal tools that provide visibility into the customer journey, enable structured feedback loops, and evolve into a role-optimized GTM experience.

• Own product discovery and delivery from strategy to execution, aligning cross-functional teams across Engineering, Design, and GTM stakeholders.

• Define and execute the roadmap for Harbour, balancing short-term wins with long-term innovation.

• Monitor and report on performance of your initiatives to senior leadership

• Collaborate with all Growth and Business Technology PMs to prioritize key strategies and initiatives for Harbour

To be successful, you should have:

• Product management experience in a SaaS or technology-driven company, ideally building internal platforms, AI-powered tools, or systems that support go-to-market (GTM) teams.

• A strong ability to translate across technical and non-technical domains - you’re comfortable working with stakeholders across the business to drive alignment and clarity.

• Strong analytical skills, with a track record of using data, customer insights, and systems thinking to inform decisions, optimize workflows, and product outcomes.

• Ability to independently drive initiatives, manage multiple priorities, and operate with a high degree of autonomy while still collaborating with senior leadership for alignment.

• Show strong leadership and decision-making abilities, with a proactive approach to identifying problems and proposing innovative solutions.

• Exceptional communication, strategic thinking, and execution skills — and the ability to motivate teams around bold goals.

Highly desired (but not a deal-breaker) if you had:

• Familiarity with CRM systems (e.g., Salesforce, HubSpot)

• Experience building LLM-powered products.

• Knowledge of Retrieval Augmented Generation (RAG), context tuning, and AI evaluations

Compensation:

At Jobber, we believe that compensation should be transparent, fair, and reflective of your experience and growth. This role has a minimum annual salary of $125,800, a midpoint of $147,900, and a maximum salary of $170,100, designed to show the progression from learning the ropes to truly excelling.

We design our compensation to reflect each new hire’s skills, experience against the complexity of the role, ensuring a fair and competitive salary. Our range is intentionally broad to support growth and long-term impact, with fully established hires typically starting around the midpoint. The higher end of the range is reserved for those who have demonstrated deep expertise and lasting contributions, while offers below the midpoint reflect strong potential with room to develop. This approach ensures that compensation aligns with both an individual’s current capabilities and their opportunity for future growth.

Base salary is just one part of a total compensation package that will include equity rewards, annual stipends for health and wellness, retirement savings matching, and an extended health package with fully paid premiums for body and mind. Your professional growth matters to us too! You’ll have access to a dedicated talent development program that includes career coaching and opportunities for career development.

We believe in transparency and open conversations about compensation. If you have any questions about our approach, we’re happy to discuss them throughout the hiring process!

What you can expect from Jobber:

• A total compensation package that includes an extended health benefits package with fully paid premiums for both body and mind, retirement savings plan matching, and stock options.

• A dedicated Talent Development team and access to coaching, learning, and leadership programs to help you grow your career, reach your goals, and unlock your full potential.

• Support for all your breaks: from vacation to rest and recharge, your birthday off to celebrate, health days to support your physical and mental health, and parental leave top-ups to support your growing family.

• A unique opportunity to build, grow, and leave your impact on a $400-billion industry that has no dominant player...yet.

• To work with a group of people who are humble, supportive, and give a sh*t about our customers.

We believe that diverse teams perform better and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.

A bit more about us:

Job by job, we’re transforming the way service is delivered. Your lawn care provider, home cleaning service, plumber or painter could use Jobber to better connect with their customers, save time in the office, invoice faster, and get paid! We’re bringing tens of thousands of people together with technology to deliver billions of dollars a year in services to happy customers. Jobber exists to help make these small businesses successful, and when they’re successful we all win!