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Michael S.

Michael S.

Program & Project Delivery Lead | Enterprise Agile Transformation

I specialize in leading complex programs, stabilizing at-risk initiatives, and transforming delivery into predictable, measurable outcomes. I am a Program Delivery Lead and Transformation Advisor with 15+ years of experience managing large-scale, multi-million-dollar technology programs across federal, financial services, and highly regulated environments. I am typically engaged when programs are off-track, governance is weak, delivery lacks predictability, or executive confidence has eroded. I bring deep expertise across the full program and project lifecycle—from strategic planning, funding alignment, and roadmap development through execution, release management, and operational deployment. I operate at both the program and delivery levels, ensuring alignment between portfolio objectives, program execution, and team-level delivery. My experience includes leading complex, multi-team and multi-vendor programs, where I establish structure, enforce delivery discipline, and drive cross-functional coordination. I implement governance models, integrated master schedules, dependency management frameworks, and risk controls that enable leadership visibility and decision-making. I specialize in environments where: • Programs are behind schedule, over budget, or failing to deliver expected outcomes • Delivery lacks structure, governance, or accountability • Stakeholders require clear, reliable reporting and execution transparency • Multiple teams, vendors, and dependencies must be aligned under a single program • Agile must operate within enterprise governance, compliance, and regulatory constraints What I do best: • Lead end-to-end program delivery, from initiation through execution and release • Establish program governance, PMO structures, and delivery frameworks • Recover failing or underperforming programs and restore stakeholder confidence • Drive integrated planning (roadmaps, PI Planning, release planning, master scheduling) • Manage cross-team dependencies, risks, and critical path execution • Implement delivery metrics, dashboards, and executive reporting (Jira, Azure DevOps) • Align Agile execution with program governance, funding, and compliance requirements I combine hands-on delivery leadership with strategic program oversight. I work directly with executives, PMOs, Product, Engineering, and vendors to remove bottlenecks, improve execution discipline, and ensure programs deliver on their intended business and mission outcomes. My experience includes leading enterprise modernization efforts such as large-scale Salesforce transformations and federal mission systems, where I have reset delivery models, introduced governance, and restored execution predictability. If you need a program leader who can bring structure to complexity, enforce execution discipline, and deliver outcomes across large, multi-team initiatives, I can help.

🇺🇸Bowie, United States$50/hr100% JSS5.00 (1)Since Jan 2026

Earnings and projects

MRR
$146

Last 6 months ÷ 6

World#124,289 / 412k
🇺🇸Country#17,128 / 62.1k
Revenue, last 30 days
$0

Last 6 months: $875

Total earnings
$2.3k

Billed in all: $2.5k

World#320,934 / 412k
🇺🇸Country#49,579 / 62.1k
Per project
$2.3k

$875 in the last 6 months

World#68,935 / 412k
🇺🇸Country#11,557 / 62.1k
Projects, last 6 months
1
0% fixed100% hourly
World#128,092 / 412k
🇺🇸Country#16,472 / 62.1k
Projects in all
1
0% fixed100% hourly
World#360,671 / 412k
🇺🇸Country#53,151 / 62.1k

Earnings, last 30 days

$2.5kNothing earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$2,450$2,500$2,550$2,600Oct 8Oct 23Nov 7

Skill rankings: Top 22% in Agile Software Development

Ranked by MRR among everyone on Upwork with the skill.

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