Training and Implementation Consultant (Sales)

Pinewood.AI

3d•Hybrid

About The Position

Pinewood.AI is seeking a knowledgeable and people-focused Training and Implementation Consultant specializing in dealership sales operations. You’ll work directly with dealership sales teams, sales managers, GSMs, internet directors, and leadership to ensure a smooth transition to our Automotive Intelligence Platform. This is a hands-on role where you’ll combine your expertise in dealership sales workflows with implementation, configuration, and training skills. You’ll play a key part in helping sales teams adopt new processes, build confidence in the platform, and drive consistent execution from onboarding through long-term adoption. 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 challenges, 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 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%).

Responsibilities

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.