Training Specialist – Accounting

Summary

Lightspeed DMS provides cloud-based dealer management software for powersport, marine, RV, trailer, and golf car dealerships. The Training Specialist – Accounting trains dealership clients remotely on accounting, financial reporting, reconciliation, and best-practice workflows within the Lightspeed DMS platform, while supporting go-live engagements and dealer-specific troubleshooting.

Responsibilities

• 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

Skills

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

Qualifications

Must Haves

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

Nice to Haves

• 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

Benefits

• Fully remote position