Sales Enablement Specialist (AE)

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 are looking for a Sales Enablement Specialist to drive and support key initiatives across our Revenue Organization, with a strong emphasis on upskilling our Account Executive (AE) team members within our Emerging (SMB) and Mid-Market segments through a combination of proactively creating and enhancing sales processes, sales resources, sales technology, and sales training. 

While this will be your core focus, we’re looking for someone excited to operate as a generalist—someone who is energized by executing on our sales strategy but equally comfortable flexing into ongoing enablement needs as the business evolves. This role will play a pivotal part in broader enablement initiatives, ranging from tech stack adoption and sales campaign execution to call quality enhancements and everboarding programs. This is a highly cross-functional role that supports scalable, impactful enablement across the go-to-market team.

What You’ll Do:

• Create and maintain sales enablement resources (e.g., playbooks, tech stack training, library of sales stories, etc.).
• Gather and relay feedback from sales stakeholders to iterate on enablement strategy.
• Partner with Revenue Enablement & Sales Leadership to identify onboarding and ongoing learning opportunities.
• Use performance data to identify knowledge and skill gaps across the team.
• Collaborate with Product Marketing on competitive intelligence and battlecards, and deliver training on new product launches.
• Work closely with Revenue Operations to operationalize process and methodology updates.
• Facilitate engaging training sessions and enablement programs to improve win rates and increase deal sizes across the Account Executive team.
• Standardize best practices into repeatable and scalable tools to accelerate ramp and consistency across all reps, ex: email templates, call scripts, demo flows, or qualification guides.
• Develop frameworks and templates that help Account Executives better articulate value, conduct discovery, manage their deals, handle objections, and differentiate in competitive sales cycles.
• Establish and track success metrics for enablement programs, e.g. ramp time, demo-to-close conversion, or content adoption, and iterate based on feedback and outcomes.
• Contribute to a high-performing, collaborative Enablement culture that sets a high bar for excellence and accountability.

About You:

• You’re a proactive problem-solver who takes pride in making others successful
• You have strong GTM acumen, training methods, and a deep understanding of how to drive sales performance 
• You have excellent communication skills and are skilled in creating effective training materials
• You’re a builder, a collaborator, and a team player who thrives on making an impact
• You’re highly organized with strong project management skills and a sharp attention to detail—able to drive initiatives from idea to execution
• You’re highly coachable and take ownership of your growth—you seek feedback, act on it, and are always looking to level up

Your Experience:

• 3+ years of experience in a SaaS Sales Enablement role.
• 4+ years of experience in a sales role within a SaaS or B2B company (preferably as an Account Executive or Account Manager).
• Deep knowledge of sales methodologies and processes, with experience in MEDDPICC, Command of the Message, & Challenger.
• Proven experience building and maintaining enablement resources for Account Executives.
• Proficiency in industry-standard sales tools (e.g., Salesforce, Scratchpad, Outreach, ZoomInfo, Gong, ChiliPiper, LinkedIn Sales Navigator, Nooks).
• Experience working within an LMS is a strong asset, with WorkRamp being a plus.
• Experience in CMMS, B2B SaaS startups, or growth-stage companies
• Bachelor’s degree in business, marketing, product, communications, org development, education, or a related field 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.