Training Specialist – Accounting

Overview

This role is a Training Specialist – Accounting supporting dealership clients remotely on accounting, financial reporting, and reconciliation workflows within the Dealer Management Solution (DMS). You’ll combine software training expertise with real accounting knowledge to help dealers close their books accurately, understand their financial statements, and adopt best-practice accounting workflows in the DMS.

Each engagement follows a structured 6-week go-live and follow-up training cycle. The position is fully remote, with the ability to travel for an annual team meeting.

Responsibilities

• Lead a pre-call with each dealer’s accounting staff to introduce the role, review current processes and pain points, and set expectations for a smooth transition through go-live
• Deliver structured 1:1 accounting training across a 6-week go-live and follow-up cycle (approximately 12 hours per dealer), covering standard milestones and daily tasks
• Guide dealers through go-live week essentials, including:
  • Clearing and beginning balances
  • Chart-of-accounts mapping
  • Preferences and tax settings
  • Data recreation
  • Daily close procedures
• Train on accounts payable and accounts receivable workflows, including:
  • Accounts payable: flooring, vendor setup, reporting, packing slips
  • Accounts receivable: debit/credit memos, funding, and customer accounts
• Reinforce system audits, tax reporting, bank reconciliation, clean financial statements, and month-end close through weekly 1:1 sessions in weeks two through six
• Serve as the dealer go-to resource for real-time accounting questions and dealer-specific troubleshooting
• Coordinate with the onsite/virtual go-live trainer to ensure a consistent, connected experience for the dealer
• Maintain detailed dealer notes (outstanding items, follow-ups, decisions) so nothing is missed across training weeks and team handoffs

Requirements

• 2+ years of experience in accounting, bookkeeping, or controller-support roles, ideally within a dealership environment (Powersports, RV, Marine, Trailer, Golf, or OPE)
• Hands-on experience with a dealership DMS—Lightspeed Evolution preferred—including accounting modules such as:
  • Accounts payable
  • Accounts receivable
  • Bank reconciliation
  • Month-end close
• Working knowledge of dealership-specific accounting processes such as flooring, vendor packing slips, and dealer/customer funding
• Strong verbal and written communication skills, with the ability to explain accounting concepts clearly to non-accountants
• Highly organized and detail-oriented, with the ability to manage multiple dealer engagements and schedules concurrently
• Comfortable working independently in a remote, multi-time-zone team environment
• Proficiency with standard virtual meeting and training tools
• Fully remote position; ability to travel for an annual team meeting

Preferred Qualifications

• Prior training, coaching, or customer-facing support experience
• Bachelor’s degree in Accounting, Finance, or equivalent experience
• Strong interpersonal soft skills (setting/managing expectations, conflict resolution, etc.)
• Ability to consult and collaborate cross-functionally with other departments
• Ability to handle an increasingly high volume of work in a fast-paced, deadline-driven environment while staying calm

Compensation & Benefits

• Remote: $50,000 USD - $86,510 USD

Location

• Fully remote
• Ability to travel for an annual team meeting

Work Authorization

• Applicants must be authorized to work in the U.S.