Senior Director Business Enablement

The Senior Director of Business Enablement is accountable for ensuring that Trail’s technology, data and enterprise systems drive measurable business outcomes, innovation and long‑term value creation across the organisation. The role leads business technology enablement, ensuring ERP, future CRM, analytics and data platforms are effectively prioritised, adopted and continually optimised to unlock operational efficiency and tangible value.

• 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, behavioural change and process discipline associated with new system capabilities
• Measure and report on value realisation, 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 organisational 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

• Oversee prioritisation, sequencing, dependencies and change capacity for enablement projects
• Provide strategic visibility into priorities, organisational capacity, risks and trade‑offs
• Actively escalates conflicts between business demand, system readiness and organisational 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 prioritisation of analytics that directly support operational, financial and commercial decisions

• Assist with predictive analytics initiatives (e.g., demand, inventory, pricing, marketing)
• Help identify and scale an AI strategy for Trail to drive automation, productivity and new use‑cases
• Operationalise 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, cyber‑security or platform architecture
• System uptime, environments or release mechanics
• Software engineering or development team management

• Bachelor’s degree in Business, Technology, Engineering or a related field (required)
• MBA or equivalent advanced degree strongly preferred
• 10–15+ years of progressive leadership experience in business transformation, technology enablement or digital operations
• Proven experience owning or enabling enterprise platforms (ERP, CRM), ideally Microsoft Dynamics 365
• Demonstrated success driving enterprise‑wide change management and adoption initiatives
• Experience leading or partnering with a PMO, including prioritisation, sequencing and capacity planning
• Strong track record of translating…