Director, Project Management

Job Title: Director of Project Management Location: Hybrid onsite - open to multiple locations such as Greenwich, CT; Richmond, VA; Alpharetta, GA; or Minneapolis, MN Compensation: $70 - 90/hr. on a W2 basis Duration: 3-month contract to hire opportunity Not open to 3rd parties Summary: Looking for a Director of Project Management to join an Enterprise Project Management Office (EPMO) and internal consulting function. This is a high-impact individual contributor role responsible for leading complex, enterprise-wide transformation initiatives across a network of 50+ operating insurance companies. Key Responsibilities: Lead large, complex enterprise transformation programs from problem definition through successful delivery. Independently take ownership of programs typically spanning 6-12 months, with significant enterprise visibility and potentially substantial budgets. Break down ambiguous business and technology challenges, develop practical solutions, build alignment, and establish a clear path to execution. Develop and manage comprehensive program strategies, roadmaps, milestones, dependencies, risks, budgets, and delivery plans. Drive cross-functional execution across multiple business units, operating companies, technologies, and stakeholder groups. Partner with executive leadership to establish priorities, secure decisions, communicate progress, and resolve issues. Manage relationships with external vendors, systems integrators, consulting firms, and other strategic partners. Coordinate multiple workstreams simultaneously while maintaining focus on critical business outcomes. Identify risks, dependencies, and roadblocks early and proactively drive resolution. Establish accountability across stakeholders and ensure commitments, decisions, and deliverables remain on track. Translate complex technology and data concepts into clear business implications and executive-level communications. Support transformation initiatives involving emerging technologies, including AI-enabled efficiency and transformation opportunities. Ensure programs deliver sustainable business and operational improvements, not simply technical implementations. Skills Needed: 10+ years of professional experience in project or program management Demonstrated success leading large-scale enterprise transformation or program management initiatives. Experience within Insurance or Financial Services is required; experience with an insurance carrier is highly desirable. Proven experience leading complex programs involving data, technology, business process, or operational transformation. Strong understanding of data migration, data transformation, ETL, and/or enterprise data initiatives. Experience managing both internal stakeholders and external vendors or consulting partners. Demonstrated ability to communicate effectively with senior executives, including SVP, EVP, COO, and CEO-level stakeholders. Ability to work effectively across Technology, Data/Analytics, Finance, Claims, Legal/Regulatory, and Operations. Strong problem-solving skills with the ability to bring structure to ambiguous or poorly defined challenges. Experience managing multiple workstreams, priorities, and stakeholders simultaneously. Strong executive presence, communication, influencing, and negotiation skills. Highly proactive and persistent; comfortable driving decisions, following up with stakeholders, and maintaining accountability without significant oversight. Consulting experience is valuable, particularly experience leading enterprise-scale transformation programs. PMP and/or Lean Six Sigma certification preferred. Any experience with Workday and/or Guidewire is preferred. Experience leveraging AI as an augmentation and productivity tool is a plus. Demonstrated history of professional stability and sustained performance. The successful candidate will quickly establish credibility with senior stakeholders, bring structure to complex and ambiguous problems, and independently drive major initiatives forward. #J-18808-Ljbffr Oliver James Associates Ltd.