[Hiring] Training Specialist @Lightspeed DMS

Role Description

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.

• 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.

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.

Requirements

• 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

• Remote work flexibility.
• Salary range: $50,000 — $86,510 USD.

Inclusion and Diversity at Lightspeed

At Lightspeed, we celebrate the uniqueness of every individual and encourage diverse perspectives. We believe that inclusion drives innovation and fosters meaningful connections. We are committed to building an environment where everyone feels valued and empowered to make an impact.

Equal Employment Opportunity Statement

Lightspeed is an Equal Opportunity Employer and is dedicated to building a diverse and inclusive workforce. All qualified applicants will be considered for employment without regard to race, color, creed, ancestry, national origin, gender, sexual orientation, gender identity, gender expression, marital status, religion, age, disability, veteran status, or any other protected category.

Important Note

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

Ready to apply?

Take the next step in your career—apply today and join a team where your skills will make an impact!