AI-Driven Customer Success Specialist — Travel & Adoption

Constellation Dealer Group; United States; Remote; CAD 95,000 - 115,000; Full time

Job summary

Ideal Computer Systems, a Constellation Software company, is hiring a Customer Success Specialist to drive dealer adoption and engagement for TargetCRM across North America. You’ll own dealer relationships, deliver onboarding and training, and use AI tools to scale outreach and prevent churn.

Travel up to 20% and a focus on SMB customers, with a hands-on, proactive approach to ensuring customers achieve value and renew. Join a mission-critical SaaS team focused on customer success.

Qualifications

• 2-4 years in Customer Success, account management, or SaaS support.
• Experience owning a customer portfolio and working directly with SMBs.
• SaaS onboarding experience, including kickoff calls, configuration, and go-live prep.
• Confidence delivering virtual training and product walkthroughs.
• Proactive, organized approach to managing multiple priorities.
• Comfort working independently and creating structure in an evolving environment.
• Working knowledge of AI tools for communications and workflow automation.
• Strong relationship-building and communication skills.

Responsibilities

• Serve as the primary relationship contact for TargetCRM dealers.
• Monitor product usage and engagement to identify healthy, inactive, and at-risk accounts.
• Lead proactive outreach and re-engagement campaigns to prevent churn.
• Deliver onboarding, training, feature-adoption sessions, and coaching.
• Handle product how-tos, configuration questions, and basic troubleshooting.
• Configure new customer environments and support data onboarding.
• Validate go-live readiness and support business-unit onboarding.
• Identify expansion opportunities and connect needs with Sales.
• Use AI tools to scale communications, segment accounts, and surface risks.
• Build repeatable customer-engagement processes and playbooks.
• Maintain accurate account records in Salesforce.
• Share recurring customer issues and insights with internal teams.

Skills

Customer Success

Account management

SaaS onboarding

Virtual training

AI tools

Relationship building

Tools

CRM software

TeamSupport

Microsoft 365

Twilio

Job description

Ideal Computer Systems, a Constellation Software company, is hiring a Customer Success Specialist to drive dealer adoption and engagement for TargetCRM across North America. You’ll own dealer relationships, deliver onboarding and training, and use AI tools to scale outreach and prevent churn.

Travel up to 20% and a focus on SMB customers, with a hands-on, proactive approach to ensuring customers achieve value and renew. Join a mission-critical SaaS team focused on customer success.