Customer Success Specialist

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

Travel: Up to 20% Across North America is required.

Ideal Computer Systems, a Constellation Software company, provides mission-critical dealer management software to equipment dealerships across North America. TargetCRM is our communication and CRM platform, helping dealers manage customer relationships, marketing, and messaging at scale.

We’re hiring a hands‑on Customer Success Specialist to drive dealer adoption, engagement, retention, training, and onboarding. You’ll own relationships across the dealer base, proactively identify at‑risk accounts, provide front‑line support, and help customers get lasting value from TargetCRM.

What You’ll Do

• 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 help prevent churn
• Deliver onboarding, product training, feature‑adoption sessions, and workflow coaching
• Handle product how‑tos, configuration questions, and basic troubleshooting
• Configure new customer environments, support data onboarding, and validate go‑live readiness
• Support Business Unit partners with training and customer onboarding
• Identify expansion opportunities and connect qualified needs with Sales
• Use AI tools to scale communications, segment accounts, automate follow‑ups, and surface risks
• Build repeatable customer‑engagement processes and playbooks
• Maintain accurate account records in Salesforce
• Share recurring customer issues, product gaps, and insights with internal teams

What You Bring

• 2-4 years of experience in Customer Success, account management, or SaaS support
• Experience owning a customer portfolio and working directly with SMB customers
• SaaS onboarding experience, including kickoff calls, configuration, and go‑live preparation
• Confidence delivering virtual training and product walkthroughs
• A 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

Nice to Have

• Experience with CRM, dealer management software, or vertical‑market SaaS
• Knowledge of equipment dealerships, automotive, powersports, marine, RV, or related industries
• Familiarity with TeamSupport, Microsoft 365, Twilio, or messaging compliance

Salary Range (Ontario & BC Only): The estimated base salary range for this role is CAD$95 - CAD$115K, plus Corporate Bonus yearly- based on experience. We include salary ranges in job postings only where required by applicable pay transparency laws, based on the jurisdictions in which the role may be performed. The posted range is a good faith estimate and reflects factors that are subject to change. Final offer amounts may vary based on job‑related factors, including work location, candidate experience and expertise, and other relevant considerations.

Human-Centered, AI-Supported: We may use AI tools to support and streamline parts of our recruitment process, such as scheduling, and note‑taking. AI helps us work more efficiently and consistently, but it never replaces human judgment. All hiring decisions are made by people not machines. Interviews are conducted by real team members who want to get to know you and your experience. AI is used to reduce bias, improve fairness and streamline processes, while keeping human connection and individual stories at the heart of our process.

We recognize the value and importance of diversity and inclusion in our communities and in the workplace. We celebrate diversity and one of our goals as an employer is to create an inclusive work environment for all employees. We are an equal opportunity employer and do not discriminate against any employee or applicant because of race, religion, sex, sexual orientation including gender identity or expression, pregnancy, national origin, age, marital status, veteran status, disability status, or any other category or characteristic protected by law.

Applicants with disabilities who would like to require a reasonable accommodation related to any part of the application process may contact us at [e-mail].