Senior Software Implementation Specialist (SaaS)

TL;DR

Senior Software Implementation Specialist (SaaS): Leading end-to-end software implementations for large dealer groups with an accent on CRM deployment and bespoke configuration. Focus on managing complex multi-stakeholder onboardings, training non-technical users, and evolving implementation playbooks.

Location: Toronto, ON

Company

hirify.global is part of the CAR Group, a global network of digital marketplace businesses operating across multiple continents.

What you will do

• Lead end-to-end implementations for complex accounts, including multi-rooftop dealer groups and OEM program rollouts.
• Configure DP360 CRM and iMotor Dealer Websites to align with client business structures and workflows.
• Conduct structured kick-off calls and scoping sessions to accurately capture complexity and align stakeholders.
• Provide hands-on training to dealership staff, from owners and GMs to frontline employees.
• Mentor junior Implementation Specialists and perform QA reviews of their work before go-live.
• Act as a senior liaison between clients and internal Product, Sales, and Technical teams for high-visibility engagements.

Requirements

• 4+ years of experience in software implementation or technical account management within a B2B SaaS company.
• Proven track record of managing enterprise clients or large dealer group accounts.
• Experience training non-technical end users across various seniority levels.
• Ability to mentor junior colleagues and serve as an escalation point for complex technical issues.
• Strong organizational skills to manage a portfolio of concurrent complex implementations.
• Experience in cross-functional coordination across Product, Sales, and Support teams.

Nice to have

• Experience with DP360 CRM, Salesforce, or HubSpot in multi-user environments.
• Background in dealership verticals such as automotive, powersports, RV, marine, or commercial truck.
• Experience developing implementation playbooks and QA frameworks.
• Knowledge of OEM programs and brand-standard compliance requirements.

Culture & Benefits

• Inclusive and supportive work environment with opportunities for global mobility via the CAR Group.
• Generous leave policy with up to 31 days of paid time off in the first year.
• Comprehensive health package including medical, dental, and vision insurance.
• Financial security with a 401K plan and company match.
• Professional development through LinkedIn Learning and other continuing education resources.
• Wellness program and a culture that prioritizes employee well-being.