Enterprise Solutions Deployment Specialist

TL;DR

Enterprise Solutions Deployment Specialist (TMS): Lead end-to-end deployments for complex enterprise accounts in transportation management software with an accent on configuration architecture, change management, and AI-augmented processes. Focus on designing stable platform configurations, resolving deployment risks, and contributing to methodology evolution.

Location: Hybrid in Toronto (office Mon/Tue/Thu, WFH optional Wed/Fri)

Salary: $97,000–$121,000 CAD + commission

Company

Market leader in Transportation Management Software revolutionizing the trucking industry with SaaS solutions.

What you will do

• Lead full deployment lifecycle for enterprise accounts from kickoff through go-live
• Facilitate kickoffs, configuration workshops, UAT, and manage timelines with executive stakeholders
• Design tailored platform configurations optimized for stability, integrations, and business rules
• Use AI tooling for audits, action plans, and workflow improvements
• Provide feedback to Product/Engineering and collaborate cross-functionally

Requirements

• 5–10 years in enterprise software implementation (ERP, TMS, WMS) or operations roles
• Experience leading complex multi-stakeholder deployments
• Deep knowledge of software configuration: fields, workflows, permissions, integrations
• Analytical skills with data and metrics
• Strong communication for executive meetings and documentation
• Comfort in fast-paced, evolving environment

Nice to have

• Revenue Operations or Implementation leadership background
• AI productivity tools experience
• Change management in multi-department deployments
• Transportation/logistics familiarity
• Deployment methodology contributions

Culture & Benefits

• Comprehensive benefits + health spending account
• Parental leave top-up and stock options
• MacBook and tech setup provided
• 3 weeks vacation + option to buy more, winter closure, 3 personal days
• Downtown Toronto office with coffee shop, pizza oven, rooftop patio
• "More human, less corporate" culture focused on impact and team wins