Are you ready to shape the future of how home service businesses get discovered, build their reputation, and win more work? Jobber is looking for a Senior Director of Product, Win Work to lead our marketing and sales tools portfolio and drive meaningful commercial impact for small businesses.
Jobber is the leading platform for home services, helping businesses that keep our homes and communities running. We work with home service providers — from landscapers and cleaners to contractors and specialty trades — to transform the way work is delivered through technology. With Jobber, they can quote, schedule, invoice, communicate with customers, and get paid, all while offering a smooth, professional experience.
Running a small business today is complex. Customer expectations are rising, technology is evolving rapidly, and owners need tools that work the way they do. That’s why we give them the power and flexibility to run their business 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, Deloitte’s Technology Fast 50™, and more. With over a decade of building for home service businesses, we’ve come a long way — but we’re just getting started.
This is a remote-first role open to candidates in Canada or the the following United States: California, Colorado, Georgia, Maryland, Massachusetts, Minnesota, New Jersey, New York, Texas, Utah
The Win Work group builds the tools that help small businesses attract, engage, and convert customers — from online presence and reputation to marketing campaigns and lead management. These products represent a fast-growing and increasingly strategic part of Jobber’s business, combining mature offerings with emerging AI-driven opportunities.
The Role
Reporting to the SVP of Product, you will define and execute the vision for Jobber’s Marketing and Sales product portfolio. You’ll lead a team of Product Managers responsible for a multi-product portfolio with significant revenue, retention, and monetization impact.
You’ll bring commercial rigor, strong product intuition, and deep customer empathy — and you’ll work across Jobber to ensure our products deliver measurable value for service providers and meaningful growth for Jobber.
Key Responsibilities
Strategic Leadership
Develop and execute a bold, multi-year strategy for Jobber’s marketing and sales tools portfolio.
Balance investment across improvements to mature products, expansion into new segments, and major 0→1 opportunities.
Conduct broad and deep customer discovery to understand how service providers attract and win jobs, and convert that insight into strategy and product direction.
Collaboration & Cross-Functional Leadership
Partner closely with Engineering, Design, Analytics, Marketing, Sales, and Customer Success to identify gaps, shape product capabilities, and bring offerings to market.
Work with product marketing and GTM partners to drive adoption, attach, and overall commercial performance.
Communicate product vision, decisions, and results clearly to leadership and cross-functional stakeholders.
Customer Impact & Product Excellence
Champion the voice of the customer and define workflows that help service providers get noticed online, earn trust, and convert leads more effectively.
Establish strong feedback loops to iterate quickly and deliver high-quality, intuitive product experiences.
Integrate AI meaningfully into customer-facing experiences, helping service providers market and sell with greater efficiency and consistency.
Commercial Impact
Deliver measurable business impact by scaling adoption, engagement, and retention across the portfolio.
Influence pricing, packaging, and value communication to ensure clear ROI for customers and revenue growth for Jobber.
Maintain a balanced portfolio that supports short-term goals while building long-term foundations.
Performance & Measurement
Define KPIs for the Win Work portfolio and hold teams accountable to outcomes.
Use data and qualitative insight to evaluate product health, make tradeoffs, and prioritize improvements.
Continually refine functionality based on performance, customer feedback, and market trends.
8+ years in Product Management, with experience leading teams of 5+ Product Managers.
Experience owning a meaningful SaaS product portfolio with revenue growth and customer retention responsibility
Background in vertical SaaS and strong intuition for SMB customer needs; MarTech or CRM experience is a plus but not required.
Proven expertise in pricing, packaging, and commercialization.
A balance of strategic vision and willingness to dive deep into customer problems and product details.
Strong cross-functional leadership and a collaborative, “we over I” mindset.
Hands-on experience building or scaling AI-powered products.
Exceptional communication and storytelling skills that can motivate and align diverse stakeholders.
At Jobber, we do important work — helping small home service businesses succeed. You’ll build industry-defining products that help service providers attract more customers, stand out in their markets, and grow sustainably. You’ll join a collaborative, mission-driven team that values impact, learning, and ownership.
If you’re excited about building the future of how small businesses win work and leading a high-performing product team to do it, we’d love to meet you.
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, matching in RRSP, TFSA or FHSA, 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.
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.
Please note: Our Talent team at Jobber will be offline for a holiday break, starting December 24th and extending until January 2nd. We’ll be back to go through applications and reach out with an update on your candidacy once we return in January! Happy Holidays!
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!
