Jason Orloske

About Jason Orloske

Transformational and accomplished Project Portfolio and Project Management Office (PMO)…

Experience

1. Project Portfolio Management Consultant & Delivery Practice Lead

   Digineer

   Oct 2021 — Present

   Senior-level project portfolio and PMO consultant. Assisting in the pre-sales and client proposal process, as well as helping redesign the sales process. Developed AI strategies to drive operational efficiencies, collaborating with clients and technical experts to create intelligent solutions that maximize organizational value. Advised and strategized with clients on AI-driven transformations.Client Engagements:Progressive Insurance, Program Manager & Transformation Mgmt. Office Leader, May 2024-PresentManaging a $200M+ claims system replacement from a legacy on-premise to Guidewire\'s ClaimCenter SaaS application, encompassing 16 teams, two vendors, and onshore and offshore staff of nearly 200.Cigna/Express Scripts, IT Deliver Manager with Core Platforms Dept, October 2023 – May 2024 o Managed a $4M portfolio of technology Core Platform projects and the project management staff overseeing them. Collaborated closely with other departmental Delivery Managers to ensure cross-functional initiatives stayed on track and delivered expected business outcomes.Self Esteem Brands, IT Dept. reporting to the CIO, February 2023 – September 2023o Strategized and implemented a structured, proactive, and managed approach to taking in, evaluating, and prioritizing IT project requests.o Led an effort to create a $3M enterprise data strategy that included large infrastructure changes, reporting enhancements, and organizational change management (OCM).APi Group, Business Process Transformation (BPT) Dept, October 2021 – January 2023 o Interim Project Management Office (PMO) Director managing a $7.5M project portfolio of up to nine projects, eight project staff, and managing 3rd party work, both on and offshore.o Enhanced project management processes to be SOX compliant and utilized consistently by all project staff. o Integral member of the BPT Department’s leadership team, providing input into key decisions and leading prioritization of requested projects.

Education

• Winnow Professional Training

  CSM, Product Development

• University of Wisconsin-River Falls

  B.S., Business Communication

  1994 — 1998

• University of Mary

  Masters of Project Mgmt (MPM), Project Management

  2011 — 2012

• Project Management Training Institute (PMTI)

  PMP, Project Management

  2010 — 2010

• James Madison University

  Professional Certification, Certified Manager (CM)

  2009 — 2009

Skills

• Project Management
• Relationship Building & Management
• Agile Project Management
• Program Management
• Project Portfolio Management
• Portfolio Management
• Strategic Planning
• Business Strategy
• Business Intelligence
• Software Project Management
• Mentoring
• Social Networking
• Blogging
• Change Management
• International Project Management
• Cross-Functional Team Leadership
• Leadership
• Agile Methodologies
• Sdlc
• Process Improvement
• Management
• Project Planning
• Requirements Gathering
• Training
• Team Building
• Quality Assurance
• Testing
• Certified Project Manager
• Scrum
• Project Governance
• Product Management
• Software Documentation
• Strategic Leadership
• Analysis
• Software Development Life Cycle (Sdlc)
• Business Alignment
• Health Information Exchange
• IT Project & Program Management
• Healthcare Consulting
• Presentations