Training and Implementation Consultant – Sales

Role Overview

• Deliver end-to-end implementations of Pinewood.AI for dealership sales operations, from discovery and scoping through configuration, training, go-live, and after care.
• Configure and validate sales workflows including lead management, opportunity tracking, desking, F&I handoffs, inventory visibility, CRM processes, and reporting.
• Design, adapt, and deliver high-quality training to mixed-ability audiences, from entry-level sales consultants to sales managers and executive leadership, both on-site and remotely.
• Create and localize training materials for the North American market, tailoring terminology, spelling, examples, and process detail for North American sales environments.
• Coach best practices for dealership sales processes including lead response, pipeline management, compliance, reporting accuracy, desking, and performance optimization.
• Support business change activities such as stakeholder alignment, adoption planning, sales process standardization, and training effectiveness.
• Capture lessons learned, contribute to implementation playbooks, and mentor colleagues to raise capability across the training and delivery teams.
• Collaborate closely with product, support, and delivery teams to resolve issues, share customer feedback, and continuously improve the rollout experience.
• Travel extensively across North America (approximately 80%) to deliver on-site consultancy, training, and go-live support.

Requirements

• Significant background in dealership sales operations, CRM and DMS administration, internet sales, or variable operations, with strong exposure to end-to-end sales processes.
• Demonstrable experience in training, facilitation, and change management for enterprise software platforms (DMS, CRM, desking, or sales enablement tools).
• Hands-on experience configuring and validating sales workflows within dealership systems.
• Experience designing curriculum and training assets, including localization for new markets.
• Proven ability to manage complex, single and multi-site rollouts and ability to influence senior dealership stakeholders.
• Familiarity with major dealership systems such as CDK, Reynolds, Dealertrack, Vin Solutions, eLead, Drive Centric, or comparable CRM and desking platforms.
• Excellent communication and presentation skills, with the ability to engage, motivate, and coach mixed-ability sales audiences.
• Highly organized, analytical, and comfortable managing multiple implementations concurrently.
• Proven track record of improving training methodology, adoption outcomes, or implementation effectiveness across a team or organization.
• Experience working within fast-growing or international technology companies, ideally in startup-style environments.
• Strong understanding of how effective sales execution and CRM discipline drive dealership performance and profitability.
• Adaptable, proactive, and comfortable operating in a fast-changing environment.
• Willing and able to travel extensively across the United States and Canada (around 80%).

Benefits

• A very competitive salary
• Generous car allowance
• Excellent bonus scheme
• Flexible mix of home and office working
• 4 weeks PTO
• 401k
• Excellent health insurance benefits
• Regular 1-2-1s and career development opportunities