What is the role of a Implementation Specialist at Dealerware?

The Implementation Specialist position at Dealerware is a Full-time or part-time position opportunity in the Information Technology field.

Where is this Implementation Specialist job located?

Kingston (Downtown), Ontario, K7L, Canada

What type of employment is offered for this Implementation Specialist role?

Full-time or part-time position

What is the expected salary for this Implementation Specialist job?

Compensation will be discussed during the hiring process.

How can I apply for the Implementation Specialist position at Dealerware?

You can apply directly through the application link provided.

Implementation Specialist at Dealerware

Implementation Specialist

About Dealerware

Dealerware transforms the automotive retailers of today into the mobility network of tomorrow. Launched in 2016, Dealerware manages tens of thousands of vehicles at dealerships in North America across every major manufacturer brand. Dealerware is committed to being a people-first culture and a great place to work for all, with flexible scheduling, unlimited PTO, extensive benefits, a core value of Diversity, Equity & Inclusion, and a leadership and management team that defaults to being supportive and accessible. In 2026, Dealerware was recognized by Built In as one of their Best Startups to Work for in Austin for the fifth consecutive year.

Dealerware’s team is currently hiring for an Implementation Specialist. The Implementation Specialist is responsible for executing and coordinating successful onboarding and launch of the Dealerware platform for dealership customers. This role combines project coordination, platform configuration, customer enablement, and performance tracking to ensure customers achieve value quickly and are set up for long-term success.

As an Implementation Specialist, you will own:

Training, Enablement, & Launch Support

Deliver engaging virtual training sessions and occasional in-person enablement.
Own and execute onboarding timelines, ensuring milestones and launch dates are met.
Lead the setup, configuration, and optimization of Dealerware and B2C rental websites, ensuring launch and B2C site readiness, including validation of configurations, workflows, and user access.
Assist in preparing training agendas, collateral, and follow-up communications.
Reinforce platform best practices to drive early adoption and customer satisfaction.
Stay up to date on new features and product updates to continuously improve onboarding quality.

Customer Support & Communication

Serve as the primary point of contact for assigned dealerships during onboarding and training.
Set clear expectations with customers regarding onboarding scope, timelines, and responsibilities.
Proactively communicate progress, blockers, and next steps to Sales and the Customer Success Manager throughout implementation.
Route technical issues and escalations to internal teams with clear documentation and context.
Provide post-training reinforcement and best practice guidance.

Performance Monitoring & Reporting

Monitor customer usage and performance during the first 15 calendar days post go-live.
Identify adoption gaps, churn risks, and performance issues, and proactively recommend corrective actions to the Customer Success Manager.
Contribute to customer-facing success summaries and performance reports.

Documentation & Internal Improvement

Document dealership workflows and internal processes to support continuous improvement.
Follow best practices and onboarding playbooks, suggesting edits as appropriate.
Support maintenance of training materials, SOPs, and customer-facing resources.
Share insights with cross-functional teams to improve product and service delivery.
Prepare onboarding wrap reports highlighting risks, wins, and recommendations for Customer Success handoff.

Cross-Functional Collaboration

Partner with Sales and CSMs to ensure a smooth handoff, including understanding customer goals, use cases, and configuration requirements.
Collaborate with the Customer Enablement Program Manager to continuously improve training delivery and materials.
Work with Product, Partnerships, and Customer Experience teams to communicate customer feedback and implementation challenges.

Key Performance Indicators (KPIs)

Time to value
Customer effort score
Customer sentiment
On-time implementation rate
Training completion rate
Dealer no-shows
Go-live success rate (no major issues within first 2 weeks)
Early adoption metrics (e.g., active users, transactions, utilization)
Days to kickoff, configuration, training, and CS handoff

Required Qualifications

1–3 years of experience in implementation, customer success, operations, or SaaS account support.
Passion for working directly with customers to drive successful outcomes.
Excellent organizational and multitasking skills.
Strong communication (written & verbal) and interpersonal skills.
Dynamic and effective presentation skills.
Comfort working in dashboards, spreadsheets, and performance data.
Strong problem-solving skills and ability to navigate ambiguity.
Ability to travel domestically periodically for top accounts up to 10% of the time.

Even better if you have:

Experience in the automotive industry.
Experience with CRM, project management, or onboarding tools.

Dealerware offers you:

Competitive base salary with bonus incentive eligibility
Full benefits (medical, dental, vision, disability)
401(k) with company match
On-demand educational courses via LinkedIn Learning
Tuition reimbursement and continuing education
Unlimited paid vacation policy
Flexible work
Generous Paid Parental Leave program
Modern office and a dynamic team in downtown Austin with free parking
Friendly, small company environment with a progressive culture

Dealerware is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity or including transgender status), sexual orientation, marital status, military service and veteran status, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances. Dealerware's management team is dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities, access to facilities and programs and general treatment during employment.

*We are interested in every qualified candidate who is eligible to work in the United States. However, we are not able to sponsor visas.

Implementation Specialist at Dealerware – Kingston (Downtown), Ontario

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