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Sales Enablement Manager

North America

MaintainX is the world's leading Asset and Work Intelligence platform for industrial and frontline environments. We are a modern IoT-enabled cloud-based tool for reliability, safety, and operations on physical equipment and facilities. MaintainX powers operational excellence for 12,000+ businesses including Duracell, Univar Solutions Inc., Titan America, McDonald's, Brenntag, Cintas, Xylem, and Shell.

We recently completed a $150 million Series D funding round, bringing our total funding to $254 million and valuing the company at $2.5 billion.

We’re seeking a world-class Sales Enablement Manager to elevate the performance of our XDR Organization (Sales Development Representatives + Business Development Representatives). This role is all about equipping reps and our frontline managers with the skills, coaching, and resources they need to consistently generate high-quality pipeline.

This is a highly cross-functional role where you’ll partner with XDR leadership and other cross-functional partners to ensure our reps are confident, effective, and continuously improving. If you’re passionate about coaching, training, and building scalable enablement programs that directly drive revenue impact, this is the role for you.

What You’ll Do

  • Develop and deliver scalable training programs on core competencies, including prospecting best practices, messaging, objection handling, qualification, and discovery frameworks.
  • Reinforce sales methodologies (SPIN, MEDDPICC, Challenger, value selling) through workshops, role plays, and continuous learning.
  • Listen to live and recorded calls to provide targeted coaching, surface best practices, and identify areas for improvement.
  • Coach frontline managers on how to run effective call reviews, pipeline coaching sessions, and development conversations with their teams.
  • Create and maintain enablement resources (call guides, objection libraries, persona/industry insights, competitive positioning, playbooks).
  • Drive tech stack adoption and proficiency (Salesforce, Outreach, etc.), ensuring reps and managers operate with confidence.
  • Analyze performance data and call insights to identify skill gaps and implement focused enablement interventions.
  • Support onboarding and everboarding programs to ramp new hires quickly and continually upskill tenured reps.
  • Gather and synthesize feedback from reps and managers to evolve training content, resources, and coaching practices.
  • Foster a culture of coaching and continuous improvement, empowering both reps and managers to self-diagnose and refine their approach.
  • Champion AI adoption across the XDR team, integrating AI-driven tools and insights into training, coaching, and workflows to maximize rep effectiveness and scale best practices.

About You

  • 3+ years in Sales/Revenue Enablement (or a related role focused on rep development, coaching, or training) within a SaaS environment.
  • 3+ years as a sales professional in SaaS or B2B (SDR/BDR/AE experience strongly preferred).
  • Proven expertise in coaching reps and managers - including listening to calls, providing actionable feedback, and driving behavior change.
  • Strong knowledge of modern sales methodologies (MEDDPICC, Challenger, SPIN, value selling, etc.).
  • Experience building and delivering training programs and enablement resources that scale across teams.
  • Proficiency with sales tools such as Salesforce, Outreach, Gong, Nooks, ZoomInfo, etc.
  • Excellent communication and facilitation skills, with the ability to influence at all levels of the organization.
  • Thrives in a fast-paced, high-growth environment where adaptability and creativity are key.
  • You embrace AI-powered sales enablement and are skilled at integrating AI tools into coaching, training, and workflow optimization.
  • Bonus: Experience with PLG and ABM strategies or in CMMS/B2B SaaS startups.
  • Frontline SDR or BDR Manager Experience is a plus. 

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 make the life of blue-collar workers easier worldwide by creating software that meets their needs and realities. Our product is truly life-changing for 80% of the workforce that doesn’t work behind a desk and needs enterprise-grade software at their fingertips.

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.

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