Customer Success Enablement Manager at MaintainX · Toronto

MaintainX is the world's leading AI-powered maintenance and asset management platform, serving 13,000+ customers including Duracell, Shell, Cintas, and Brenntag. We raised $150M in Series D funding led by Bessemer Venture Partners and Bain Capital Ventures, bringing our total funding to $254M. We were named to the Forbes 2025 Cloud 100, the definitive ranking of the top 100 private cloud companies in the world.

We are hiring a Customer Success Enablement Manager to own the systems, skills, and standards that enable our post-sales teams including Customer Success and Professional Services to deliver consistent value, faster time-to-value, and measurable customer outcomes at scale. 

This role is not about running training sessions for the sake of it. It is about changing behavior and directly impacting retention, expansion, and long-term customer success.

Why this role matters:

As MaintainX scales, post-sales execution becomes increasingly complex. Customers span multiple sites, stakeholders, and industries, and expectations for value realization continue to rise.

We need a dedicated enablement individual who can:

• Define what “great” looks like across post-sales roles
• Translate strategy into repeatable, role-based execution
• Reduce customer time-to-value and employee ramp time
• Drive measurable improvements in retention, expansion, and Net Dollar Retention

This role sits at the intersection of Customer Success, Professional Services, Product, and Revenue Enablement and owns post-sales enablement strategy end-to-end, from definition through execution and measurement.

What you'll do:

• Design and deliver scalable enablement programs that build post-sales capabilities across the full customer lifecycle and journey. This includes, but is not limited to, customer relationship management, value-based conversations, onboarding and product adoption execution, structured consulting engagements, renewal readiness, expansion support.
• Establish and maintain role-based curricula and learning programs for Customer Success Managers and Implementation Consultants in partnership with CS, Professional Services, and Enablement leadership.
• Partner with the New Hire University Program Manager to support onboarding and everboarding programs that accelerate ramp time and continuously upskill tenured post-sales team members.
• Create, maintain, and evolve enablement and training resources for the post-sales organization, including playbooks, frameworks, methodologies, process guidance, and industry best practices.
• Equip Customer Success Managers with frameworks and tools to deliver effective Business Impact Reviews, articulate ROI, and lead value-based conversations tailored to customer personas, industries, and levels of seniority.
• Enable Implementation Consultants with structured guidance, tools, and best practices to deliver consistent, high-quality onboarding experiences and drive faster customer time-to-value.
• Provide one-on-one coaching, feedback, and targeted training to post-sales team members to strengthen customer interactions, technical confidence, and problem-solving effectiveness.
• Analyze performance data, customer outcomes, and call insights to identify knowledge and skill gaps and prioritize enablement initiatives across post-sales roles.
• Drive improvement in key post-sales outcomes such as Net Dollar Retention, churn reduction, expansion readiness, and onboarding effectiveness through focused, measurable enablement efforts.
• Gather and synthesize feedback from post-sales team members and managers to continuously evolve training content, resources, and coaching practices.
• Champion thoughtful adoption of AI-driven tools and insights to scale coaching, learning, and enablement effectiveness across the post-sales organization.
• Measure the impact of enablement programs using qualitative and quantitative inputs, iterating continuously to ensure programs deliver clear, measurable business results.

About you:

• You are a systems thinker who designs enablement for scale, not one-off training events.
• You are comfortable influencing senior stakeholders and driving alignment without formal authority.
• You have a deep understanding of how post-sales execution drives retention, expansion, and long-term customer value.
• You combine strong instructional design skills with a pragmatic, outcome-oriented mindset.
• You are highly organized, detail-oriented, and able to drive initiatives from concept through execution.
• You’re a builder, a collaborator, and a team player who thrives on making an impact
• You take ownership of your growth and actively seek feedback, improvement, and impact.

Your experience:

• 3-5 years of experience in Customer Success, Professional Services, or post-sales roles within a B2B SaaS environment
• 2-4 years of dedicated Enablement, readiness, or field enablement experience.
• Proven ability to build and maintain scalable enablement programs that drive behavior change and measurable business outcomes.
• Experience supporting Mid-Market and Enterprise post-sales teams.
• Strong familiarity with post-sales tooling such as Salesforce, Gainsight, Gong, or similar platforms.
• Experience working within an LMS or enablement platform, with WorkRamp experience a plus.
• Exposure to CMMS, industrial SaaS, or high-growth B2B environments is a plus.
• Bachelor’s degree in business, marketing, product, education, organizational development, or a related field is a plus.

What success looks like in the first 12 months:

• Clear post-sales execution standards are defined, documented, and reinforced through enablement.
• New post-sales hires ramp faster and more consistently across segments.
• Managers are equipped to coach effectively against defined competencies.
• Enablement programs show measurable impact on time-to-value, retention, and expansion metrics.
• Post-sales teams view enablement as a critical partner in their success.

What’s in it for you:

• Competitive salary and meaningful equity opportunities.
• Healthcare, dental, and vision coverage.
• 401(k) / RRSP enrollment program.
• Take what you need PTO.
• A Work Culture where:
• You’ll work alongside folks across the globe that reflect the MaintainX values, Smart Humble Optimist.
• We believe in meritocracy, where ideas and effort are publicly celebrated.

About us:

Our mission is to deliver one platform for maintenance, repair & operations teams to keep the physical world running. We believe the greatest asset in any organization is the people. That’s why we built an intuitive, mobile-first solution to help boost productivity and collaboration across teams and locations.

MaintainX is committed to creating a diverse environment. All qualified applicants will receive consideration for employment without regard to race, colour, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.