Revenue Enablement Manager at MaintainX in Canada

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 looking for a world-class Revenue Enablement Manager: a senior, high-ownership practitioner who can independently drive impact across two critical areas of our business. You will own live onboarding facilitation for our growing revenue organization and serve as the dedicated enablement partner for our XDR (BDR/SDR) organization. This is not a coordinator or support role. You will design and run programs, facilitate high-quality live training, coach reps and managers, and operate with significant autonomy. The best person for this role can walk into a complex, fast-moving environment, quickly understand what great looks like, and build it. This role is ideal for someone who is passionate about pipeline generation and thrives as an enablement practitioner-generalist: someone who can design and deliver high-impact enablement initiatives across the full revenue organization. You will be a pivotal contributor to broader enablement efforts spanning tech stack adoption, sales campaign execution, call quality improvement, and onboarding and everboarding programs. This is a highly cross-functional role with direct impact on go-to-market performance. Roughly half of your time will be spent working alongside our Sales Onboarding Program Manager to deliver and improve our New Hire University (NHU) experience. The other half will be dedicated to XDR (BDR/SDR), developing and reinforcing the skills, methodologies, and behaviors that drive pipeline and quota attainment. What You’ll Do Onboarding Facilitation (~50%) Co-own and facilitate blended NHU learning experiences, including virtual live sessions, practice workshops, and online modules, for new hires across the revenue organization Partner closely with the Sales Onboarding Program Manager to continuously improve ramp time, content, and delivery quality Shadow and support existing facilitation to ensure program continuity during coverage transitions Support XDR onboarding and promotion pathing, creating structured and measurable learning experiences that guide new hires through early career milestones at MaintainX Track onboarding progress and evaluate training outcomes, including listening to recorded calls and supporting review sessions with XDR managers XDR Enablement (~50%) Develop and deliver scalable training programs for the XDR organization (SDR/BDR), covering core competencies: prospecting, messaging, objection handling, qualification, and discovery frameworks Reinforce sales methodologies (Challenger, SPIN, value selling) through workshops, role plays, and continuous learning initiatives Listen to live and recorded calls to provide targeted coaching, surface best practices, and identify skill gaps Coach frontline XDR managers on how to run effective call reviews, pipeline coaching, and rep development conversations Gather and synthesize feedback from reps and managers to evolve training content and coaching practices Across Both Areas Create and maintain enablement resources, call guides, objection libraries, playbooks, persona/industry insights, and LMS content Drive tech stack adoption and proficiency (Salesforce, Outreach, Gong, ZoomInfo, etc.) Analyze performance data and call insights to identify gaps and implement targeted enablement interventions Champion AI adoption across the teams you support, integrating AI-driven tools and insights into training, coaching, and rep workflows Track and report on program effectiveness, ensuring continuous improvement across both coverage areas About You: 4+ years in Sales or Revenue Enablement within a SaaS environment, with a track record of owning programs end-to-end and delivering measurable results 3+ years as a sales professional (SDR/BDR/AE experience strongly preferred), you understand the rep's world Proven experience facilitating live training: you're comfortable and credible in front of a room, whether it's a new hire cohort or a seasoned XDR team Strong coaching instincts and a proven track record of developing reps and managers through call coaching, structured workshops, and ongoing development conversations Operates with high autonomy: you can own multiple workstreams simultaneously and flex between priorities without needing heavy direction Solid knowledge of modern sales methodologies (MEDDPICC, Challenger, SPIN, value selling) Proficiency with sales tools: Salesforce, Outreach, Gong, ZoomInfo, Nooks, or similar AI-forward mindset: you actively integrate AI-powered tools and approaches into your programs, coaching, and day-to-day workflows Thrives in fast-paced, high-growth environments where adaptability is a competitive advantage Experience building LMS content and multimedia training materials is a strong asset Bonus: Frontline XDR or AE manager experience; familiarity with PLG/ABM strategies or CMMS/industrial SaaS 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.