Sr Exec Advisor Technology

POSITION OVERVIEW:

Provide expertise and leadership through the planning, coordination, and execution of strategic initiatives, organizational priorities, and special projects across Freight Technology. Serve as a trusted advisor to senior executive leadership by driving alignment, enabling execution, and facilitating collaboration across Technology, Operations, Commercial, and Corporate functions. The role operates as a strategic advisor, trusted partner, and force multiplier for the Senior Vice President, serving as a key connector across executive leadership, functional teams, and individual contributors to ensure priorities are executed effectively and consistently.

The Sr. Executive Advisor partners closely with the Technology Chief of Staff and other executive leaders to drive alignment, accountability, decision-making, and execution of enterprise priorities.

• Provide strategic counsel and execution support to Senior Executive leadership on key business, technology, and organizational priorities.
• Partner with the Senior Vice President to establish, communicate, and monitor strategic objectives, transformation initiatives, and critical business outcomes.
• Establish and manage the executive operating cadence for the Senior Executive’s organization, including leadership meetings, business reviews, strategic planning cycles, decision tracking, action management, and organizational scorecards.
• Collect, analyze, and synthesize information to support executive decision-making, including development of recommendations, trade‑off analyses, and executive briefings.
• Serve as a central coordination point for strategic escalations, ensuring issues are properly assessed, stakeholders are aligned, options are evaluated, and decisions are prepared for executive review.
• Coordinate and drive execution of cross‑functional initiatives that span multiple technology organizations and business functions.
• Facilitate alignment between Technology and business stakeholders, ensuring priorities, dependencies, risks, and decisions are effectively managed.
• Represent the Senior Vice President in meetings, governance forums, planning sessions, and cross‑functional initiatives as required.
• Develop executive‑level communications, presentations, briefing materials, business reviews, and strategic recommendations.
• Lead special projects and strategic initiatives that advance organizational effectiveness, technology modernization, operational excellence, and business value realization.
• Identify execution risks, organizational barriers, and interdependencies; proactively drive resolution and escalation as appropriate.
• Establish program governance, reporting mechanisms, milestones, and performance indicators to ensure successful initiative delivery.
• Support annual planning, portfolio reviews, operating reviews, investment prioritization, and strategic roadmap development.
• Foster collaboration across all levels of the organization, including executive leadership, management teams, technical professionals, and business stakeholders.
• Coordinate activities across multiple teams to ensure alignment to enterprise objectives and technology strategy.
• Partner closely with the Technology Chief of Staff and other Executive Advisors to ensure consistent execution of enterprise priorities.
• Analyze organizational trends, performance metrics, and strategic opportunities to support executive decision‑making.
• Assist leadership in driving change management, organizational readiness, and stakeholder engagement efforts.
• Act as a liaison between Technology, Operations, Commercial, and Corporate functions to improve communication, transparency, and execution.
• Comply with all applicable laws/regulations, as well as company policies/procedures.
• Perform other duties as assigned.

• Bachelor’s degree in business, Information Systems, Technology Management, Organizational Leadership, or related field
• Seven (7) years of relevant experience in strategic planning, program leadership, project management, business operations, technology leadership support, consulting, or organizational transformation
• Experience supporting…