Role overview

Jobber is seeking a Success Enablement Manager to join the Success Enablement team in Toronto. Jobber helps small home service businesses—plumbers, painters, landscapers, and similar trades—run their operations through software that handles quoting, scheduling, invoicing, and payment collection. This role will support the growth and performance of Product Support and Customer Onboarding teams by building the programs, playbooks, and tools that drive operational excellence and skill development.

Key responsibilities

Own the complete enablement lifecycle for Product Support and Customer Onboarding teams, from new hire ramp-up and certification through continuous development for experienced specialists.
Build and maintain the needs discovery and product positioning frameworks that specialists use in live customer conversations to match the right product to the right customer at the right time.
Create and maintain playbooks for Support and Onboarding that cover activation paths by plan and industry, adoption plays for underused features, objection handling, and retention conversations, ensuring consistency across channels.
Design, build, and test enablement content in multiple formats—in-person, virtual, and on-demand—and partner with Knowledge Management to make guidance available within the flow of work.
Work with the QA function to turn quality trends into targeted coaching and training that closes the loop between measurement and teaching.
Collaborate with Product Marketing, Success Operations, and Analytics to identify gaps and develop resources such as customer stories and competitive intelligence that help specialists advance conversations.
Connect enablement programs to business outcomes by tracking activation, feature adoption, retention, CSAT, and qualified opportunities, and report on program effectiveness.

Requirements

Demonstrated experience in customer success, customer service, onboarding, or sales within a high-volume, short-cycle B2B SaaS environment with a track record of achieving targets and motivating others.
Previous experience in revenue-driven roles with measurable targets, such as in Sales or Retention.
Experience building and executing playbooks and training programs that improve both service quality and commercial outcomes.
Strong project management skills, including the ability to create workback plans that drive projects from conception to completion.
Deep understanding of customer activation and adoption, including what drives first value and long-term product usage, and how to design enablement that supports both.
Working knowledge of needs-based selling conversations, including the ability to teach specialists how to uncover customer problems, connect them to relevant products or features, and communicate value clearly.

What makes this role worth considering

The Enablement team operates as a Center of Excellence within Jobber’s Customer Success organization, working cross-functionally to ensure every team member has the knowledge and support to deliver value. You will directly influence how Product Support and Customer Onboarding specialists operate, with clear visibility into outcomes such as faster customer activation, longer retention, and greater product adoption. Jobber has been recognized by Great Place to Work, named to Canada’s Most Admired Corporate Cultures, and listed among Deloitte Canada’s Technology Fast 50 and the Globe and Mail’s Canada’s Top Growing Companies.