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.
Travel is a significant part of this role. You will be on the road around 80% of the time, working directly with dealerships.
Key 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.
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%).
Benefits- A very competitive salary
- Flexible mix of home and office working
- 401k
- Excellent health insurance benefits
- Regular 1-2-1s and career development opportunities
