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Salary: CAD 181,400 - 245,500 / annual
Jobber is a B2B SaaS platform helping small home service businesses (plumbers, painters, landscapers) manage quoting, scheduling, invoicing, and payments. The company has been recognized by Great Place to Work and named to Deloitte Canada's Technology Fast 50 and Globe and Mail's Canada's Top Growing Companies lists.
The Sales Enablement & Operations department builds systems, tools, and people development to turn go-to-market strategy into execution. The Director, Sales Enablement will lead the Enablement Programs pillar and report to the Sr. Director, Sales Enablement & Operations, managing a team of five to six enablement managers and practitioners.
Key responsibilities include:
- Setting strategy for onboarding, training, certification, and coaching across the sales organization
- Building, managing, and upskilling a team of enablement managers and practitioners
- Owning ramp programs and certification standards, defining what "certified and ready" means
- Leading enablement for new product, pricing, and process launches with detailed workback plans
- Building structured, repeatable playbooks and coaching frameworks that evolve with product and market changes
- Integrating AI into enablement delivery (content creation, coaching feedback, practice/roleplay, knowledge access) and into rep workflows
- Partnering with Product, Product Marketing, Sales leadership, and Customer Success to align enablement with business priorities
- Defining success metrics beyond completion rates: ramp time, certification pass rates, pipeline and revenue impact
You will be accountable for outcomes—whether reps are actually ready, whether launches land in the field, and whether enablement investment shows up in ramp speed, pipeline, and revenue.
REQUIREMENTS:
- Extensive experience in sales enablement, revenue operations, or sales leadership, including building and running onboarding, training, or certification programs at scale
- Demonstrated people leadership experience, including managing managers, with a track record of developing team skills alongside field performance
- Proven track record leading enablement for product or pricing launches in B2B SaaS, with workback plans that hold against real launch timelines
- Hands-on fluency with AI tools in enablement work: content generation, coaching and roleplay, knowledge management
- Experience building structured, scalable learning frameworks rather than one-off training events
- Strong stakeholder management with director-level and senior partners across Product, Marketing, and Sales; ability to influence roadmap and go-to-market timing
- Comfort operating with ambiguity and building infrastructure where none exists
- Sharp written and verbal communication
- Bias toward outcomes over activity, with judgment to distinguish between them
