Training and Implementation Consultant (Accounting)

Pinewood.AI

2d•Hybrid

About The Position

Pinewood.AI is seeking a knowledgeable and people-focused Training and Implementation Consultant specialising in dealership accounting. You’ll work directly with dealership accounting teams, controllers, business managers and financial managers to ensure a smooth transition to our Automotive Intelligence Platform. This is a hands-on role where you’ll combine your expertise in dealership financial operations with implementation, configuration, and training skills. You’ll play a key part in helping finance teams embrace new ways of working, building confidence and efficiency during onboarding and beyond. With our North American expansion underway, this is very much a start-up environment within a well-established global business. We’re looking for someone who thrives on change, embraces challenge, and brings a proactive, can-do attitude to building something new. Travel is a significant part of this role. You will be on the road around 80% of the time, working directly with dealerships.

Requirements

Significant background in dealership accounting, finance, or F&I operations with strong exposure to end-to-end financial processes.
Demonstrable expertise in training, facilitation, and change management for enterprise software (DMS or accounting/ERP platforms).
Hands-on experience configuring and validating financial workflows within dealership systems.
Experience designing curricula and training assets, including localisation for new markets.
Proven ability to manage complex multi-site rollouts and influence senior stakeholders.
Familiarity with major dealership management and financial systems such as CDK, Reynolds, Dealertrack, or similar platforms.
Excellent communication and presentation skills, able to engage and motivate mixed ability audiences.
Highly organised, analytical, and comfortable prioritising across concurrent projects.
Proven track record of improving implementation or training methodology across a team or organisation.
Experience working with fast-growing or international technology companies, ideally in startup-style environments.
Strong understanding of how dealership financial performance drives overall dealership success.
Adaptable and proactive, thriving in a fast-changing, start-up environment.
Willing and able to travel extensively across the United States and Canada (around 80%).

Responsibilities

Deliver end-to-end implementations of Pinewood.AI for dealership accounting and finance, from discovery and scoping through configuration, training, go-live, and hypercare.
Configure and validate financial workflows, including GL mappings, journal entries, reporting, integrations with OEMs, and third-party systems.
Design, adapt, and deliver high-quality training to mixed-ability audiences, from entry-level clerks to controllers and financial directors, both on-site and remotely.
Create and localise training materials for the North American market, tailoring terminology, spelling, examples, and process detail for US users.
Coach best practices for dealership financial workflows, including AP/AR, bank reconciliations, manufacturer statements, compliance, and month-end processes.
Deliver business change activities such as stakeholder alignment, adoption planning, and measurement of training effectiveness.
Capture lessons learned, contribute to implementation playbooks, and mentor colleagues to raise capability across the team.
Collaborate with product, support, and delivery teams to resolve issues, share feedback, and improve the overall rollout process.
Travel extensively across North America, approximately 80% of the time, to deliver on-site consultancy and training.