Customer Success / Account Representative (Expansion & Retention) — Heavy Equipment Rental SaaS

Just Sales Jobs; Toronto; On-site; CAD 67,000 - 81,000; Full time

Job summary

A technology solutions provider in Ontario is seeking a Customer Success / Account Representative to manage and grow a portfolio of existing customers. The role focuses on customer retention and expansion using a cloud-based software platform. Candidates should have a strong record in sales and customer management, with excellent communication skills. A competitive salary and benefits package, including performance bonuses, is offered in a flexible remote work environment.

Benefits

Base salary with performance bonus

RSP Matching

Health benefits

Furthering Education Reimbursement

Qualifications

• Proven track record of upselling and cross-selling within a customer base.
• Customer Success Manager or Account Manager experience preferred.
• Demonstrated ability to drive product adoption and manage customer retention.

Responsibilities

• Manage and grow a portfolio of existing customer accounts.
• Focus on customer expansion and retention.
• Conduct quarterly business reviews and targeted check-ins with key accounts.

Skills

Excellent verbal/written communication

Relationship-building

Presentation skills

Experience in upselling and cross-selling

Education

4 years of sales experience in software SaaS or related industries

Tools

CRM – Proficiency with HubSpot or similar platform

MS Office – Intermediate

Job description

As a Customer Success / Account Representative you will be responsible for managing and growing a portfolio of existing equipment rental and industrial customers using our clients cloud-based software platform. This role is focused on customer expansion (tier upgrades, additional user licenses, module adoption), retention, and ensuring long-term platform value—not net‑new business development or cold calling. You will manage approximately 60‑80 customer accounts after ramp‑up. Your success will be measured by account growth (ARR expansion), renewals, and minimizing churn. This position offers a base salary ranging from $67,000 to $80,600 plus performance bonus.

Compensation & Benefits

• Base salary: $67,000 to $80,600 plus 15% bonus depending on performance
• First Year OTE: $77,000 – $93,000
• RSP Matching
• Laptop provided
• Health benefits
• Furthering Education Reimbursement

The Company & Culture

Our client is a SaaS company that provides rental management, fleet tracking, service scheduling, invoicing, and financial solutions for equipment rental and industrial businesses across North America. It is privately owned, established over 30 years ago, and continues to grow through product innovation. The culture is collaborative, customer‑focused, and performance‑driven. Teams are supportive, decisions are transparent, and leadership encourages initiative, problem‑solving, and professional development. The environment is approachable, respectful, and driven by continuous improvement.

Office Location & Sales Territory

• Head Office: Mississauga, Ontario
• Work Model: Primarily remote with 12 days per quarter in office for meetings and team collaboration
• Territory: North America (servicing existing accounts across the U.S. and Canada)
• Hours: Monday to Friday regular business hours

Experience Background & Education Requirements

• 4 years of sales experience in software SaaS or related industries
• Proven track record of upselling and cross‑selling within a customer base
• Excellent verbal/written communication, relationship‑building, and presentation skills
• Customer Success Manager or Account Manager experience preferred
• Demonstrated ability to drive product adoption and manage customer retention
• Heavy equipment, service, or rental background is an asset

Technical Skills

• CRM – Proficiency with HubSpot or similar platform
• MS Office – Intermediate
• Video conferencing & screen sharing tools
• Account management & data tracking software
• Basic data analysis & reporting tools

Product / Service / Solution

• Cloud‑based SaaS platform for equipment rental and industrial companies
• Modules include: contract & rental management, fleet maintenance, service scheduling, inventory, work orders, finance, and analytics

Prospective Customers / Industry Focus / Decision Makers

• Existing customers: equipment rental companies, construction rental, industrial service companies
• Decision‑makers: Operations Managers, General Managers, Controllers, Fleet Managers, Owners, IT Leaders
• Accounts are categorized as Expand, Maintain, or Save based on health and opportunity

Sales Cycle / Order Value / Account Size

• Renewals range from 12 to 36 months

Competitive Advantages

• Industry specialization & 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

• Account management and relationship building across assigned book of business (60‑80 accounts)
• Strategic upselling and cross‑selling opportunities through proactive customer engagement
• Product adoption enablement and training to drive increased customer usage
• Account status assessment and tailored outreach based on account needs (maintain, save or expand)
• Risk mitigation and retention activities for at‑risk accounts
• Initial triage and absorption of customer escalations before routing to management when necessary
• Quarterly business reviews and targeted check‑ins with key accounts
• Building CS processes and customer enablement curriculum to support customer success

Leads

• No hunting or cold calling – 100% existing customer accounts
• Expansion ARR through tier upgrades, adding licenses, and additional modules

Overnight Travel

• Minimal occasional travel for large accounts, trade shows or QBRs (less than 10%)

Support & Training

• 23 weeks of onboarding sales/product training
• Shadowing current Customer Success Managers and Implementations Team
• Coaching from Director of Customer Success
• Expected to manage accounts independently within 46 weeks

Why You Should Apply

• No cold calling – fully relationship and growth‑focused role
• Stable base salary with predictable bonus model
• Ability to directly influence revenue while building long‑term partnerships
• Flexible mostly‑remote structure with supportive leadership
• Career advancement to Senior CSM or leadership within 12‑24 months

Our client is an equal opportunity employer committed to creating a diverse and inclusive, barrier‑free workplace. They strive to provide a safe, healthy and respectful workplace where individuals are valued for their contributions. Our client encourages applications from women, Aboriginal peoples, members of visible minorities and persons with disabilities. Our client is committed to providing an accessible and supportive recruitment experience for persons with disabilities. If you require accommodations at any stage of the recruitment process, please notify us in advance. We thank all applicants for their interest; however, only those candidates under consideration will be contacted.