Sales Strategy & Enablement Director

About the role

The Sales Strategy & Enablement Director is responsible for driving the AI vision and roadmap for the Sales and SBO organizations at Cox Automotive. This role serves as the designated AI Ambassador for Sales and SBO within the enterprise-wide AI ambassador program, ensuring these functions have an informed, engaged voice in enterprise AI governance, pilot coordination, and emerging technology evaluation.

Responsibilities

• Drives the CAI Sales and SBO AI vision and roadmap forward through the delivery system, tracking progress and maturity while ensuring the roadmap evolves as technology, vendor landscape, and business priorities shift.
• Serves as the designated AI Ambassador for the Sales and SBO organizations, representing their priorities and readiness in the enterprise-wide AI ambassador network through weekly coordination and ad hoc testing sessions.
• Pairs across the Sales Analytics, Business Process Design & Improvement, Technology, Sales, and SBO teams to evaluate how tools could converge as AI capabilities mature, including aligning AI tool build priorities and sequencing prototype and data-hardening efforts against the roadmap.
• Leads organizational readiness and positioning efforts for incoming agentic AI capabilities, developing structured evaluation criteria and sequencing recommendations before new tools enter build or pilot phases.
• Contributes to the strategic change narrative for sales leadership and the broader field organization, communicating what transformation is coming, why it matters, and how the organization will navigate it.
• Owes the structured mechanism for capturing seller feedback and channeling it back to vision-level roadmap decisions, ensuring transformation efforts remain grounded in actual seller and SBO team member experience.
• Defines vision-level success criteria and transformation measurement frameworks that assess whether the overall seller and SBO experience, sales effectiveness, and return on investment are improving, beyond individual tool adoption metrics.
• Drives strategic tool rationalization and consolidation decisions, identifying redundancy across the sales and SBO tool stack and building business cases for convergence aligned to the broader AI vision.
• Creates investment roadmaps and impact analyses aligned with future budget plans, providing clear visibility into new funding requirements and potential variances associated with AI transformation initiatives.
• Ensures Sales and SBO interests are represented in enterprise-level AI policy, platform, and governance decisions, advocating for alignment between what is being built enterprise-wide and what sellers actually need.
• Contributes to broader initiatives that enhance the overall seller experience at Cox Automotive, serving as a strategic resource available for high-priority projects and transformation efforts beyond AI-specific work.
• Pairs with the SBO Business Process Design & Improvement Team to ensure smooth handoffs between strategic transformation decisions and operational enablement execution, including tool sunset timing, migration planning, and field communication sequencing.
• Supports the development of shared governance frameworks, intake and prioritization mechanisms, handoff protocols, and citizen development standards.

Qualifications

• Bachelor's degree with 10+ years of relevant experience. A master's degree and 8 years related experience; a Ph.D. and 5 years related experience; or 14 years of related experience without a degree are also considered.
• 5+ years of experience in a strategy, transformation, or senior operations role within a complex enterprise sales or sales operations environment required.
• Demonstrated ability to develop and communicate multi-year strategic visions and translate them into actionable roadmaps with measurable milestones.
• Experience with product or program lifecycle management within a structured delivery framework (e.g., Agile or phase-gate), rather than strategic planning alone.
• Deep, hands-on familiarity with both the enterprise AI and agentic technology landscape, including tools such as Claude and Copilot M365, and the broader sales technology ecosystem, including CRM platforms such as Salesforce, CPQ, sales enablement, and conversation intelligence tools, sufficient to assess convergence and rationalization opportunities across the tool stack.
• Proven ability to operate as a strategic partner to senior sales leadership, translating business priorities into technology and transformation strategy.
• Experience leading enterprise-level transformation or change initiatives in a matrixed organization, including stakeholder alignment across multiple functions without direct authority, ideally grounded in a recognized change management framework such as Prosci or ADKAR.
• Strong ability to evaluate emerging technologies for strategic fit, organizational readiness, and business impact rather than purely technical capability.
• Excellent executive communication and presentation skills, including the ability to develop leadership-facing materials that simplify complex transformation narratives.
• Experience developing investment roadmaps, business cases, and impact analyses that support funding decisions.
• Outstanding analytical and problem-solving skills with a high degree of intellectual curiosity, including strong data gathering, reporting, and statistical analysis; the ability to define performance measurements and interpret data using concepts such as variance, correlation, and trends; and the ability to define problems, determine root causes, and translate findings into clear, actionable recommendations that connect strategic vision to operational reality.
• Comfort operating in ambiguity and evolving organizational models, with a bias toward building lightweight frameworks that can iterate rather than waiting for perfect structures.
• Familiarity with the automotive retail industry or Cox Automotive's business model is a plus.

Pay

USD 134,900.00 - 224,900.00 per year. Compensation includes a base salary in the range of $134,900.00 - $224,900.00. The base salary may vary within the anticipated base pay range based on factors such as the ultimate location of the position and the selected candidate's knowledge, skills, and abilities. Position may be eligible for additional compensation that may include an incentive program.

Benefits

• Flexible vacation with pay
• Seven paid holidays throughout the calendar year
• Up to 160 hours of paid wellness annually for their own wellness or that of family members
• Bereavement leave
• Jury duty leave
• Volunteer time off
• Military leave
• Parental leave