Job Description & How to Apply Below
Then Jobber might be the place for you! We’re looking for a Director, Customer Onboarding to join our Success department!
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
Our Success team works together with other teams and stakeholders to bring our company values to life for our customers. By being humble, supportive, and truly giving a sh
* t, the Success team ensures that our customers are successful in Jobber. This team thrives on meaningful and impactful communication with one another and with our customers, and plays a significant role in the lives of entrepreneurs and business owners that utilize Jobber.
The role
Reporting to the VP, Customer Success, the Director, Customer Onboarding will lead the strategy, execution, and evolution of one of the most critical customer-facing functions. You will be accountable for delivering a world-class onboarding experience that accelerates time-to-value and drives activation, retention, and revenue growth for new customers.
You will oversee a growing team of onboarding specialists and managers, with responsibility for outcomes including activation, net revenue retention, and customer engagement. This role works cross-functionally with Product, Sales, Revenue Operations, Enablement, and Support to deliver a seamless and scalable customer journey.
The Director, Customer Onboarding will:
Team Leadership & Development
Lead, coach, and scale a high-performing Customer Onboarding team.
Establish clear roles, development paths, and performance frameworks for ICs and managers.
Foster a culture of ownership, accountability, and continuous improvement.
Partner with Enablement to drive training, learning, and QA initiatives.
Promote cross-functional collaboration to align with broader Success, Sales, and Product strategies.
Customer Experience & Operational Strategy
Own the end-to-end onboarding journey from implementation to early success.
Evolve and scale onboarding processes across 1:1, 1:many, and tech-touch delivery models.
Leverage data and insights to optimize onboarding timelines and accelerate time-to-value.
Identify and implement best practices that increase adoption, engagement, and retention.
Performance, Tooling, and Measurement
Set and manage onboarding performance targets (activation rates, payments adoption, NRR, customer retention, CSAT).
Build dashboards and reporting frameworks in collaboration with Rev Ops.
Identify opportunities to automate workflows and streamline customer interactions.
Ensure systems (Salesforce, Chili Piper, Revenue.io, etc.) are optimized for scale and insight.
Partner with VOC teams to close feedback loops between Onboarding, Product, and Marketing.
To be successful, you should have:
Extensive experience leading Customer Onboarding, Customer Success, or implementation teams in a B2B SaaS environment.
Proven ability to develop and scale high-performing teams, including both managers and ICs.
Demonstrated…
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