Sr Director Business Enablement

The Senior Director of Business Enablement is accountable for ensuring Trail’s technology, data, and enterprise systems drive measurable business outcomes, innovation, and long‑term value creation across the organization.

This role leads business technology enablement, ensuring that ERP, future CRM, analytics, and data platforms are effectively prioritized, adopted by the business, and continuously optimized to unlock operational efficiency, innovation, and tangible value.

This role serves as the bridge between business leadership and technology platforms, owning change management, business enablement, value realization, and the translation of evolving business needs into scalable capabilities that support future growth.

• Own business enablement for enterprise platforms including Dynamics 365 and future customer‑facing systems (e.g., CRM).
• Ensure systems are configured, extended, and enhanced to support Trail across commercial, operations and finance.
• Translate strategic business priorities into clear technology initiatives and outcomes.
• Drive adoption, behavioral change, and process discipline associated with new system capabilities.
• Measure and report on value realization, adoption, and business impact.

• Act as the business owner to unlock the full value of Dynamics 365.
• Partner with Technology and business leaders to evaluate new Microsoft features, assess readiness and timing, and sequence enhancements based on organizational capacity.
• Ensure ERP evolution is deliberate, controlled, and aligned to operational realities.
• Prevent feature sprawl, workarounds, and adoption gaps.

• Lead business ownership of CRM strategy and implementation when introduced.
• Partner with Sales, Marketing, and Operations leadership to define customer journeys, pipeline and lead management, and adoption standards.
• Ensure CRM capabilities support both transactional and long‑cycle customer relationships.
• Own CRM adoption, training, and ongoing evolution.

• Overseeing prioritization, sequencing, dependencies, and change capacity for Enablement projects.
• Provide strategic visibility into priorities, organizational capacity, risks, and tradeoffs.
• Actively elevate conflicts between business demand, system readiness, and organizational capacity.

• Ensure high‑quality translation of business needs into clear, actionable requirements.
• Maintain strong alignment between business intent, system configuration, and delivered outcomes.
• Prevent “solution‑first” thinking by anchoring work in business problems and workflows.

• Own analytics and reporting as decision‑enablement tools, not standalone outputs.
• Ensure reporting, dashboards, and insights are trusted, actionable and embedded in day‑to‑day decision‑making.
• Own enterprise data models, definitions, and governance, in partnership with Technology.
• Drive prioritization of analytics that directly support operational, financial, and commercial decisions.

Working with other stakeholders

• Assist with predictive analytics initiatives (e.g., demand, inventory, pricing, marketing, etc).
• Help identify and scale an AI strategy for Trail, to drive automation, productivity and new use‑cases.
• Operationalize AI use‑cases with clear business value.

• Partner closely with all facets of the business and the Senior Leadership Team.
• Act as a trusted advisor to senior leaders on how systems, data, and process changes affect execution.
• Facilitate alignment and decision‑making across functions.

• Infrastructure, networks, cybersecurity, or platform architecture
• System uptime, environments, or release mechanics
• Software engineering or development team management

These accountabilities reside with the Senior Director, Technology

• Bachelor’s degree in Business, Technology, Engineering, or a related field required
• MBA or…