Customer Success Enablement Manager

MaintainX•Toronto, ON

About The Position

MaintainX is seeking a Customer Success Enablement Manager to lead the systems, skills, and standards that empower post-sales teams, including Customer Success and Professional Services. The goal is to ensure these teams consistently deliver value, achieve faster time-to-value, and drive measurable customer outcomes at scale. This role is crucial for impacting retention, expansion, and long-term customer success by changing behavior, not just delivering training. As MaintainX grows, the complexity of post-sales execution increases, with customers across various sites, industries, and rising expectations for value realization. This individual will define excellence in post-sales roles, translate strategy into actionable execution, reduce customer and employee ramp time, and improve key metrics like retention and Net Dollar Retention. The position operates at the intersection of Customer Success, Professional Services, Product, and Revenue Enablement, overseeing the entire post-sales enablement strategy from conception to measurement.

Requirements

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.
Systems thinker who designs enablement for scale, not one-off training events.
Comfortable influencing senior stakeholders and driving alignment without formal authority.
Deep understanding of how post-sales execution drives retention, expansion, and long-term customer value.
Combines strong instructional design skills with a pragmatic, outcome-oriented mindset.
Highly organized, detail-oriented, and able to drive initiatives from concept through execution.
A builder, a collaborator, and a team player who thrives on making an impact.
Takes ownership of growth and actively seeks feedback, improvement, and impact.

Nice To Haves

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.

Responsibilities

Design and deliver scalable enablement programs that build post-sales capabilities across the full customer lifecycle and journey, including customer relationship management, value-based conversations, onboarding and product adoption execution, structured consulting engagements, renewal readiness, and 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.