• Develop and execute technical win strategies against incumbent DMS providers, including CDK, Reynolds, and Tekion • Lead executive-level discovery sessions to uncover operational inefficiencies and platform limitations • Deliver advanced, workflow-driven demonstrations across sales, F&I, service, parts, and accounting • Map Pinewood.AI capabilities directly to financial performance, scalability, and operational impact • Surface and resolve technical objections early, eliminating perceived migration or integration risk • Support RFP responses, security reviews, compliance assessments, and technical due diligence processes • Design and deliver proof-of-concept engagements that demonstrate measurable workflow improvements • Anticipate and neutralise competitive FUD around integration, conversion risk, uptime, reporting depth, and compliance • Partner closely with Account Executives to control deal narrative, pacing, and competitive positioning