Senior Revenue Enablement & Strategy Lead

MaintainX is the leading maintenance and asset management platform. We are a modern cloud based tool for maintenance, safety, and operations on equipment and facilities. MaintainX powers operational excellence for 12,000+ businesses including Duracell, Univar Solutions Inc., Titan America, McDonalds, 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.

About the role:

As the Senior Revenue Enablement & Strategy Lead at MaintainX, you will lead the design, implementation, and continuous improvement of our sales methodology and playbook programs, with a strong focus on empowering our Enterprise Sales team. This role requires a strategic, hands-on leader who can translate sales strategy into actionable, high-impact enablement programs, enabling our team to execute, scale, and win consistently.

You’re a forward-thinking enablement professional who approaches challenges with creativity and a bias for action. You bring a modern lens to enablement—leveraging AI, enablement platforms, and sales tools to innovate how playbooks, training, and coaching programs are built and scaled across the team. This role is not just about building content; it’s about driving measurable impact. The programs you design will directly influence how the field executes, and ultimately, how we perform against revenue goals. Your work will directly support our Enterprise Sales team while helping shape the overall enablement strategy at MaintainX.

What you’ll do:

• Own and manage the end-to-end lifecycle of sales playbooks. This includes designing, delivering, and conducting ongoing iterations, ensuring clear guidance on sales motions, particularly for the Enterprise segment.
• Provide strategic insights and recommendations to Revenue Leadership on ongoing development needs and enablement opportunities. 
• Enable the field to deeply adopt and execute sales methodology and enterprise sales motions by building programs that embed these practices into the sales culture.
• Bring an innovative, tool-enabled approach to enablement, leveraging AI and sales enablement platforms to develop playbooks, streamline content delivery, personalize learning, and continuously evolve programs.
• Partner with Revenue Leadership and cross-functional teams (Marketing, Product, RevOps) to ensure enablement programs are relevant, impactful, and aligned to GTM strategy.
• Measure and report on program effectiveness, tying outcomes to revenue impact and driving continuous improvement.
• Regularly update enablement content and playbook documentation to reflect changes in process, tools, messaging, product, or market conditions.
• Apply learnings from enterprise to inform and build tailored playbooks for other segments, ensuring scalable, segment-specific sales execution.
• Design and operationalize a scalable coaching framework that empowers sales managers to reinforce the playbook, drive consistent execution, develop team skills, and ensure accountability across the sales process.

About you:

• 10+ years of experience in Revenue/GTM/Sales Enablement or Strategy with a strong track record of building and scaling playbooks and methodology programs.
• Demonstrated success enabling Enterprise sales teams and driving adoption of complex sales methodologies (MEDDPICC, Challenger, Force Management, SPIN).
• Proven ability to create and manage detailed sales playbooks tied to specific sales motions and segments.
• Experience training sales managers to lead with consistency and impact.
• Strong facilitation, communication, and project management skills.
• Innovative mindset with a passion for modernizing enablement through tools, technology, and AI-driven insights.
• Data-driven, with the ability to assess enablement impact and optimize programs accordingly.
• Familiarity with enablement and sales tools such as Salesforce, Outreach, Notion, WorkRamp, Gong or Kaia.

Bonus Points:

• Experience in a high-growth SaaS environment.
• Methodology certified in MEDDPICC, Challenger, or Force Management.
• Experience creating training and coaching programs for both PLG and Enterprise sales motions.

What’s in it for you:

• Competitive salary and meaningful equity opportunities.
• Healthcare, dental, and vision coverage.
• RRSP 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.