Director, Enterprise Project Management

About Canal Insurance

Canal Insurance Company specializes in insurance for commercial trucking and specialty transportation operations. Canal was founded in 1939 and is located in Greenville, South Carolina. At Canal, we recognize that our success would not be possible without the hard work and dedication of our employees. We know that happiness and productivity go hand in hand, and to that end, we consciously cultivate a culture that enables us to recruit and retain the very best talent in the business.

A Culture With YOU in Mind

• Located in beautiful downtown Greenville, SC
• Career growth & advancement opportunities
• Comprehensive benefits package
• Employee referral program
• Casual dress code
• Innovation-focused & customer-centric
• 80+ years of industry expertise
• Committed to giving back to our community
• Unquestioned integrity and commitment

Benefits at Canal

• Basic & Voluntary Life Insurance Plans
• Medical, Dental, & Vision
• Short Term & Long Term Disability
• 401(k) plan with company match up to 6%
• Flexible Spending Accounts
• Employee Assistance Programs
• Generous PTO Plan

Director, Enterprise Project Management

Job Summary: The Director, Enterprise Project Manager role is responsible for the overall management of the projects throughout the organization. Provides strategic direction for all projects, coordinates resources, and manages the project managers to achieve organizational objectives.

Major Accountabilities:

1. Enterprise Project Leadership:

• Direct and oversee projects from initiation to closure, ensuring defined scope, goals, deliverables, budgets, and timelines align with organizational objectives
• Develop and maintain project plans and communication frameworks, ensuring clear and timely updates to stakeholders and senior leadership
• Effectively engage and collaborate with internal and external resources, including vendor partners
• Manage project scope, schedules, and costs using established change management practices
• Identify risks, issues, and dependencies, and implement mitigation and contingency plans
• Monitor and measure project performance, providing regular reporting and driving corrective actions as needed
• Lead project teams by defining roles, responsibilities, and accountability to ensure successful delivery
• Ensure quality standards are met and actively participate in issue resolution
• Maintain project documentation and deliver executive-level reporting, presentations, and status updates
• Contribute to the development and continuous improvement of project management practices, tools, and governance

2. Vendor Management (VMO) Leadership

• Lead and scale the Vendor Management Office as a centralized function supporting enterprise needs
• Build and manage a team responsible for vendor relationship management across IT, Finance, Claims, and Underwriting
• Establish structured engagement model with vendors to ensure alignment on performance, cost, and delivery expectations
• Own end-to-end vendor lifecycle:
  o Intake of vendor requests
  o Cross-functional evaluation (business, IT, finance, risk)
  o Vendor selection and contracting support
  o Onboarding and integration into existing workflows and systems
•  Ensure all vendor-related requests are funneled through a standardized intake and governance process
•  Drive timely, data-driven vendor analysis to support informed decision-making
• Partner with Vendor Management Office, Legal, and Finance on contract structuring, cost optimization, and risk management
• Monitor vendor performance against KPIs and drive continuous improvement

3. Agile Delivery & Intake 

• Own a centralized intake model for all incoming technology and business requests, ensuring alignment to strategic priorities
• Facilitate development of business cases, including value articulation, cost-benefit analysis, and prioritization rationale
• Partner with senior leadership (SLT) to socialize and secure alignment on key initiatives
• Define and institutionalize a standardized agile delivery framework across teams (hybrid where needed)
• Ensure consistent execution practices across delivery teams (cadence, ceremonies, reporting, accountability)
• Partner with delivery managers to:
  • Drive on-time, high-quality execution
  • Manage dependencies and cross-team coordination
  • Resolve delivery risks and escalations
• Establish clear linkage between intake prioritization execution outcomes

4. Organizational Leadership & Capacity Management

• Lead and develop a high-performing team across PMO, VMO, and delivery coordination functions
• Drive professional growth through coaching, structured development plans, and performance management
• Own departmental budgeting, including resource planning, vendor spend alignment, and cost optimization
• Ensure effective capacity planning aligned to portfolio demand and strategic priorities
• Foster a culture of accountability, transparency, and continuous improvement

Qualifications:

Education/Training Requirements: Bachelor’s Degree required, PMP required.

Experience/Specialized Skills:

• 7+ years project management experience
• Influencing abilities
• Developing and managing budgets
• Vendor Management skills
• Experienced skills with MS Project
• Experience communicating effectively with all levels of management
• Experience with software methodology development processes
• Excellent Customer Facing Skills
• Excellent Communication Skills (written and verbal)
• Ability to work under tight deadlines managing multiple priorities
• Contract Negotiation
• Capitalization Management
• Demonstrated knowledge of Project Management processes and tools

Special Considerations:

Physical Requirements: Constant use of vision, hearing, and communication (oral and written in person and via telephone).  Frequent concentration, standing, walking, handling, reaching, and grasping.  Occasional bending, kneeling and lifting (up to 25 lbs.) Heavy use of computer and office equipment.

Travel/Hours of Service: Occasional travel may be required.  Periodic work outside of standard business hours or on weekends may be required.