
Jerry Glasscock
Verified Expert in Project Management
Project Manager
Dallas, TX, United States
Toptal member since March 31, 2025
Jerry is an executive leader with 20+ years of experience driving complex transformations in the public and private sectors, including the DoD, State of Alaska, Texas, and Fortune 500 companies. He leads high-impact PMOs, aligns strategy with execution, and manages global portfolios exceeding $100 million. Known for navigating complexity, aligning stakeholders, and mentoring teams, Jerry delivers results with integrity, structure, and a calm, strategic presence in dynamic environments.
Project Highlights
Expertise
- Accountability
- Communication
- Cross-cultural Collaboration
- Labor Efficiency Analysis
- Leadership
- Objectives & Key Results (OKRs)
- Organizational Effectiveness
- Senior Executive Management
Work Experience
Principal Consultant
JD Consulting
- Drove the turnaround of a $60 million distressed portfolio as director of the project management office (PMO), guiding global teams and delivering a comprehensive property and financial software suite.
- Secured a $20 million maintenance contract by delivering the turnaround of a $60 million distressed portfolio.
- Provided management consulting, strategic oversight, and tactical guidance for the implementation of Azure Data Lake, migrating legacy systems to the cloud while ensuring risk, security, and regulatory compliance.
- Led global project teams across multiple risk management business units as senior vice president, providing executive updates for the Office of the Comptroller of the Currency (OCC) and FRB Enterprise Consent Order Book of Work through to completion.
- Directed an IT and business risk-focused enterprise PMO (EPOM) to implement project management best practices, standardize reporting and processes, and upgrade tool sets, strengthening risk management capabilities to meet OCC requirements.
Vice President, Project Strategy Office
Citigroup
- Built a sustainable, high-performance culture within Citigroup's global anti-money laundering (AML) program strategy office (PMO/PSO), delivering $250 million per year in global programs with hundreds of cross-functional, cross-cultural team members.
- Managed program management teams across NAM, LATAM, APAC, and EMEA, providing strategic direction and objectives to address anti-money laundering in credit card transaction monitoring across 142 countries.
- Implemented project management best practices, including global reporting, metrics, and success criteria, to deliver the credit card transaction monitoring portfolio, avoiding over $600 million in regulatory penalties.
- Guided executive stakeholders through global planning activities and collaborated with business and technology groups to strategically manage compliance and regulatory mandates.
- Delivered executive-level reporting and escalated issues as needed to ensure regulatory compliance.
- Developed and maintained strong working relationships with lines of business and program teams.
- Directed annual planning for technology, business, and data teams to align with portfolio deliverables, develop project plans, and manage testing and integration to achieve portfolio objectives.
- Leveraged enterprise-wide platforms and resources to develop technology essential for AML solutions, overseeing the optimization of performance, quality, and cost in the delivery function by defining and implementing proper resourcing.
Director of Program Management
Transamerica
- Assumed leadership of the PMO and directed teams to rescue a distressed $60 million enterprise portfolio involving data consolidation and migration, infrastructure, and front-end and middleware transformation.
- Assessed the current state of efforts, brought in business analysts to document existing business flows, and conducted managerial workshops to finalize the future-state workflows.
- Provided assessments and recommendations to the CIO, CTO, and COO to support strategic decisions and ensure program success, incorporating technologists and strategists to enhance system efficiency and effectiveness.
- Developed a strategic plan to integrate end-of-life databases, migrate to a new system, and replace front-end systems.
- Managed consultants, 3rd-party vendors, and 250 global business and technology resources.
Senior Management Consultant
Loblolly Consulting
- Advised C-level executives, providing executive management consulting and operational transformation strategies. Acted as a trusted advisor to the COO at the Texas Department of Family and Protective Services (DFPS).
- Engaged with C-suite executives, government leaders, and key stakeholders, delivering data-driven insights, strategic recommendations, and personnel assessments to drive enterprise-wide improvements.
- Spearheaded the Texas Department of Transportation's data and infrastructure consolidation program, managing cross-functional teams across multiple agencies, contractors, consultants, and vendors, achieving 0% unexpected downtime.
- Conducted executive leadership assessments and led an IT department transformation, resulting in a 65% increase in positive customer feedback through enhanced service delivery.
- Drove an enterprise-wide inventory management overhaul, reducing property loss from 6% to 0.1% through organizational and process improvements.
- Designed and implemented organizational restructuring strategies, generating $6 million in savings and reducing inventory-related labor hours by 75%.
Senior Program Manager
Dell Financial Services/Dell
- Delivered the strategy and implementation for upgrading Info-Lease, the primary financial application for the $12 billion portfolio, and upgraded the infrastructure, including storage, computing, and network improvements.
- Provided executive and C-level communication on metrics, risks, and progress.
- Managed multiple enterprise-wide, cross-functional teams to create a project plan covering implementation, testing strategy, success criteria, deployment, system documentation, and training.
- Achieved regulatory cost avoidance, saving $10 million in tax penalties and $1 million in licensing penalties.
- Developed the PMO by standardizing project management practices across Dell Financial Services.
Project History
Global Credit Card AML Strategy and Compliance Leadership
Directed global program management teams for a $1 billion portfolio to monitor credit card transactions in 142 countries, ensuring OCC and FRB compliance and successfully preventing financial, business, and reputational damage.
My efforts were key in aligning technology, business, and data teams to deliver scalable, digital-first solutions leveraging big data analytics. I partnered closely with global executive stakeholders and regulatory bodies, overseeing strategic planning, issue escalation, resource optimization, and offshoring. My leadership helped build a sustainable high-performance culture that successfully delivered AML capabilities at scale, ensured regulatory compliance, and drove continuous process and cost-efficiency improvements across the enterprise.
Turnaround of Global Property and Financial Management Program
Assumed leadership of the PMO teams, triaged issues for prioritization, and focused on remaining work items to achieve program objectives, resulting in restored client satisfaction and signing a $20 million follow-on maintenance contract.
I led and restructured a team of 73 cross-functional professionals—including project managers, developers, business analysts, data analysts, and other specialists—using a war-room triage approach. I rapidly assessed team skill sets, reassigned resources and workstreams, and escalated key issues requiring senior-level technical expertise to resolve critical blockers.
By instilling structure, accountability, and urgency, I drove successful implementation delivery, which directly resulted in securing a $20 million long-term maintenance contract. My leadership was central to transforming a failing program into a high-functioning, results-driven initiative that met delivery timelines, ensured customer satisfaction, and preserved future revenue.
Operational Transformation and Cross-agency Collaboration in the State of Texas
Advised C-level leaders, including the DFPS COO, driving operational transformation, improving efficiency, and fostering cross-agency collaboration through high-impact initiatives.
I conducted executive leadership assessments and led an IT department transformation that resulted in a 65% increase in positive customer feedback through enhanced service delivery and operational realignment. I also led an enterprise-wide inventory management overhaul, reducing property loss from 6% to 0.1% by implementing organizational and process improvements. Additionally, I designed and executed organizational restructuring strategies that generated $6 million in savings and reduced inventory-related labor hours by 75%.
Education
Bachelor's Degree in Criminal Justice
University of Alaska - Anchorage, AK, USA
Certifications
Certified Scrum Product Owner (CSPO)
Scrum Alliance
Certified Scrum Master (CSM)
Scrum Alliance
Certified Anti-Money Laundering Specialist
Association of Anti-Money Laundering Professionals
Project Management Professional (PMP)
Project Management Institute (PMI)
Skills
Tools
Zoom, Microsoft Project, Microsoft Excel, Microsoft Word, Microsoft PowerPoint
Paradigms
Management, Agile, Waterfall Delivery, Change Management, Agile Project Management, Organizational Analysis
Platforms
Enterprise Resource Planning (ERP), Azure
Other
Leadership, Project Management, Consulting, IT Project Management, Program Management, Portfolio Management, Governance, PMO Governance, Business Transformation, Diplomacy, Compliance, Labor Efficiency Analysis, Leadership Development, Cross-cultural Collaboration, Senior Executive Management, Planning, PMO Development, PMO Maturity Assessment, Team Leadership, Waterfall, Digital Technologies, Collaboration, Delegates, Talent Management, Objectives & Key Results (OKRs), Solutioning, Strategic Decision-making, Accountability, Interdisciplinary Collaboration, PMO, Stakeholder Management, Management Consulting, Strategic Cost Reduction, Operational Efficiency Improvement, Complex Problem Solving, IT Program Management, Organizational Management, Leadership Assessment, Organizational Effectiveness, User Stories, Transformation Delivery Management, Digital Transformation Program Management, API Integration, IT Management, Strategy Development, Scaled Agile Framework (SAFe), IT Governance, Championing a Vision, Strategic Management, Anti-money Laundering (AML), Resource Management, OCC Compliance, FRB Compliance, Software Development Lifecycle (SDLC), Roadmaps, Cloud, Vendor Management, Public Speaking, Risk Management, Information Security, Business Analysis, Modernization, Innovation, Psychology, Organizational Design, Law Enforcement, Criminal Justice, Artificial Intelligence (AI), Communication, Remote Team Leadership, Executive Consulting, Scrum Master, SharePpoint, Microsoft Copilot
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