Training Specialist – Accounting

About the Role

The Training Specialist – Accounting is a key member of the Accounting Specialist Team (AST), responsible for training dealership clients — remotely — on the accounting, financial reporting, and reconciliation workflows within the Lightspeed DMS platform. This role blends software training expertise with real accounting knowledge to help dealers close their books accurately, understand their financial statements, and adopt best-practice accounting workflows inside the DMS. Each engagement follows a structured 6-week go-live and follow-up training cycle. This is a fully remote position, with the ability to travel for an annual team meeting.

What You'll Do

• Lead a pre-call with each dealer's accounting staff to introduce the AST 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 every standard milestone and daily task
• Guide dealers through go-live week essentials — clearing and beginning balances, chart-of-accounts mapping, preferences and tax settings, data recreation, and daily close procedures
• Cover accounts payable workflows (flooring, vendor setup, reporting, packing slips) alongside accounts receivable topics such as 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's go-to resource for real-time accounting questions and dealer-specific troubleshooting
• Coordinate with the onsite/virtual go-live trainer so the dealer gets one consistent, connected experience
• Keep detailed dealer notes — outstanding items, follow-ups, decisions — so nothing falls through the cracks across training weeks and team handoffs

What You Should Have

Qualifications:

• 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, and 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 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 in a calm manner