Who you are

• Proven years of experience in enablement, L&D, or QA within a SaaS or customer-focused organization; demonstrated knowledge of relevant best practices, methodologies, and technologies
• Proven leadership in building enablement strategies that serve diverse functions (e.g., onboarding, support, sales)
• Deep experience with LMS platforms, content tools (e.g., Notion, Confluence), QA frameworks, and product enablement practices
• A data-driven mindset and strong program management abilities
• Ability to coach, mentor, and scale high-performing teams
• Excellent communication and facilitation skills—across live sessions, async formats, and documentation
• Strong business acumen
• Must have a high level of curiosity, and a passion for continuous improvement
• Extremely strong analytical and problem-solving skills

What the job involves

• Our Customer 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 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 who utilize Jobber
• The Enablement Team is a central function within Jobber's Customer Success organization, supporting the growth and performance of Customer Onboarding, Product Support and Account Management
• As a Center of Excellence, Enablement owns the programs, tools, and frameworks that drive operational excellence and skill development in these areas
• We work cross-functionally to ensure that every team member—regardless of channel or customer type—has the knowledge, confidence, and support to deliver value
• As Senior Manager, Enablement, you'll be a driving force behind the design and execution of enablement programs across employee onboarding, knowledge management, quality assurance, and continuous learning
• You’ll play a pivotal role in shaping how our Customer Success teams onboard, grow, and show up for our customers across onboarding, support, and account management functions
• This is a highly autonomous, impact-oriented role—ideal for someone who thrives in ambiguity, moves quickly from insight to action, and brings fresh, creative thinking to solving complex problems
• You’re energized by building programs from the ground up, collaborating cross-functionally, and using data, feedback, and intuition to level up both team performance and the customer experience
• You understand the inner workings of high-performing Success organizations and are ready to roll up your sleeves to build systems, content, and experiences that drive real results—whether it's a smoother ramp, a smarter knowledge base, or a more confident team on the front lines
• Design and deliver onboarding, upskilling, and continuous learning programs tailored to the needs of Customer Onboarding, Product Support, and Sales Expansion teams
• Coach Enablement team members in curriculum development, facilitation, and instructional design
• Integrate feedback from Voice of Customer (VoC), QA insights, and CSAT metrics into training evolution
• Oversee the creation, organization, and maintenance of internal and external knowledge assets (e.g., playbooks, SOPs, Help Center articles)
• Ensure knowledge materials are accurate, accessible, and in line with best industry best practice for technical writing
• Partner closely with Knowledge Base Managers and content specialists to drive strategy and efficiency in self-serve resources
• Lead QA strategy for onboarding and support interactions, including call reviews, chat/email evaluations, and feedback loops
• Align QA criteria with enablement outcomes and team performance standards
• Drive cross-functional calibration sessions to ensure consistency and transparency
• Define success metrics across each enablement pillar—ramp time, QA score trends, knowledge engagement, CSAT, and more
• Report regularly on enablement impact to Success and cross-functional leadership
• Use data to iterate on training delivery, content structure, and coaching programs
• Partner with Product, Product Marketing, Operations, and People teams to ensure readiness for product releases, campaigns, and feature changes
• Influence and support change management efforts across supported functions
• Ensure enablement alignment with business goals, team targets, and customer outcomes

Benefits

• Health, dental, vision, and paramedical for both mind and body, life and travel insurance, and an employee assistance program.
• Health spending and wellness accounts to help with expenses not covered by traditional benefits.
• Equity and RRSP matching of up to 3% of your annual salary.
• Your birthday off!
• Parental leave—complete with top-ups for up to 8 weeks.
• Monthly snack box program with plenty of options for that afternoon pick-me-up.
• Bi-weekly all company stand-ups, quarterly hackathons and town halls, and yearly all-hands professional development sessions.
• Continuous 1:1’s and honest feedback.
• A team of humble and supportive group of Jobberinos who give a sh*t about the work they’re doing.
• Opportunity to have a 1:1 session with one of our Development Coaches, take advantage of our in-house suite of learning opportunities, and build out your personal development plans.
• Hybrid work model.
• Work in either our Edmonton or Toronto office, remotely from anywhere in Canada or the US, or a combination of both.
• Monthly home office allowance and a one-time stipend to help equip your home office.