Sales Executive - Heavy Equipment Rental SaaSChicago, Illinois, United StatesAbout the JobAs a Sales Executive, you will be selling SaaS platforms tailored for equipment rental, dealer, sales, and service industries. The role involves working with executive-level decision-makers and typically navigating three key stakeholders in the buying process. You will be responsible for driving new business development and securing new clients across North America. You will report to the Director of Sale. This position offers a base salary ranging from $80,000 to $110,000 plus uncapped commissions.
Compensation & Benefits:
$80,000 to $110,000 base salary, plus uncapped commissions OTE in the first year: up to $220,000 OTE in the second year: up to $220,000+ Health Benefits Company Paid RSP Matching Laptop & Cell Phone Provided Employee Recognition, Gifts, Rewards Education Reimbursement Company Social Events Full-Time Work from Home & Flex HoursThe Company & Culture Our client, founded in 1982 and headquartered in Mississauga, Ontario, is a leading provider of SaaS solutions for the heavy equipment, construction, and industrial sectors. They empower equipment dealers, rental companies, and contractors across North America to streamline operations, improve asset utilization, and drive business growth through innovative technology. The company is recognized for its commitment to customer success, continuous product innovation, and industry expertise. They foster a supportive, inclusive culture that values employee well-being, collaboration, and professional growth. The company encourages innovation, celebrates achievements, and supports ongoing learning and development. Employees are empowered to make an impact, contribute to a positive workplace, and participate in community initiatives.
Office Location & Sales Territory:
Head Office: Mississauga, Ontario Remote-based role with quarterly in-office meetings Approximately one week per month of North American travel for client visits and conferences. Sales Territory: North America (Canada & U.S.)
Hours: Monday to Friday
Experience, Background & Education Requirements 3 - 7+ years of B2B SaaS/Cloud software sales experience (new business development) Proven success selling to C-Suite decision-makers (CEO, CFO, CRO) Preferred experience selling to construction, heavy equipment, or industrial technology sectors Strong record of securing new clients/logos and closing complex enterprise-level software solutions Must be comfortable working in a high-growth, fast-paced SaaS environment Technical SkillsMS Excel Basic MS Word Basic PowerPoint Intermediate Google Drive/Docs Intermediate Online Demos Intermediate The Product / Service / Solution SaaS platform for equipment rental, sales, and service industries Solutions include customer relationship management, service delivery, inventory management, rental asset management, and business operations optimization Prospective Customers / Industry Focus / Decision Maker(s) Customers: Equipment rental houses, heavy equipment dealers, and related industrial service providers Company size: Small-to-Mid Market (2099 employees make up the majority of client base)
Location:
Primarily North America Decision Makers: C-Suite executives, owners, and financial leadership Sales Cycle / Order Value / Account Size Average Order Size: $40,000 USD ARR Average Account Size: $40,000 USD ARR Sales Cycle: 13 months, typically 68 sales calls/meetings to close Competitive Advantages IndustrySpecialization & Domain Fit Integrated Platform Across Sales, Rental & Service Advanced Asset Tracking & Proactive Maintenance Strong Reporting, Analytics & Decision Support SaaS Model with Lower IT Overhead Ease of Use & Adoption Focus Typical Day & Duties 75% New Business Development (prospecting, demos, closing new clients) 25% Administrative Duties (CRM updates, forecasting, reporting) 0% Account Management Leads 50% Prospecting / Cold Calling 25% Warm Leads from Marketing & SDRs 25% Supplied Lists Overnight Travel 25% (approximately 1 week per month across Canada & the U.S.)Support & Training Sales training: 23 months (ad-hoc, job shadowing, joint calls) Technical product training: 23 months (self-directed with support from product/marketing) Expected ramp-up: 23 months until actively selling Why You Should Apply IndustrySpecialized Leader: they focus solely on the equipment rental, sales, and service sector youll be working with a product built by experts for experts, not a generic solution. Integrated & Innovative Platform: Youll be promoting a unified system that covers rental operations, dealer sales, service workflows, and AIdriven analytics a compelling, cuttingedge offering. Impact & Ownership: In your role, youll have significant influence in shaping customer outcomes and expanding market presence your contributions will be visible and meaningful. Strong Backing & Stability: their SaaS model, cloud infrastructure, and growing market presence offer both credibility and room for growth.
