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Michael S.
Expert-Vetted

Michael S.

Enterprise Program Manager | Digital Transformation | ERP, Cloud & AI

Most businesses don’t have a technology problem. They have an execution problem. I’m an Enterprise Program Manager and Technical Transformation Leader who specializes in helping businesses confidently deliver complex technology initiatives that are risky, highly visible, or just plain too important to fail. Throughout my career spanning 25+ years, I’ve worked with executives, product teams, and engineering organizations to lead enterprise-wide transformations involving ERP, CRM, HRIS, cloud, enterprise integrations, CMS platforms, artificial intelligence, and large-scale data migrations. Whether the goal is modernizing legacy systems, integrating a stack of siloed platforms, or bringing order to a chaotic delivery organization, my focus stays the same: reduce risk and help you execute with confidence. I don’t believe great programs are won by holding status meetings and managing Excel spreadsheets. Successful programs are built on smart technical decisions, realistic delivery plans, eliminating organizational roadblocks, and keeping the lines of communication open between the business and engineering teams. On any given day, I’m just as comfortable working with executives on strategy, budgets, and roadmaps as I am digging into the details with product owners, mapping integrations with architects, validating data migrations, configuring Jira workflows, or collaborating directly with engineers to unblock delivery. I’ve led initiatives ranging from small product teams to global enterprise programs involving multiple vendors, distributed engineering teams, and executive stakeholders. Some of the initiatives I regularly lead include: * Enterprise Program & Product Management * Digital & Business Transformation * Cloud Strategy, Migration Planning, and Infrastructure Modernization * ERP, CRM, HRIS, & Contract Lifecycle Management (CLM) * Enterprise CMS Platforms, Website Migrations, and Digital Experience Platforms * Enterprise Data Migration and Systems Integration * Jira, ServiceNow, Agile Delivery, and PMO Process Modernization * Microsoft 365, Azure, AWS, Identity, Security, and Zero Trust * Artificial Intelligence Enablement and Business Process Automation I’ve had the opportunity to work with organizations like Dell, VMware, LG Electronics, Cox Communications, Enovix, along with many high-growth companies navigating major technology transformations. Some of the platforms and technologies I’ve worked with include Microsoft Dynamics 365, SAP, NetSuite, Salesforce, HubSpot, Workday, Jira, ServiceNow, Azure DevOps, Contentstack, Drupal, WordPress, Evisort, DocuSign CLM, Databricks, AWS, Azure, Microsoft 365, and many more. I typically get brought into organizations when: * They need experienced leadership on a large technology initiative. * Multiple teams or vendors aren’t aligned. * Requirements are unclear and delivery has stalled. * Cloud, ERP, CMS, or enterprise platform migrations need clear vision and structure. * Data migrations or integrations pose significant business risk. * Leadership needs someone who can understand business objectives and translate them into actionable technical plans. I don’t come in to add another management layer. I come in to remove the friction that’s keeping your organization from delivering. If you think I can help with your technology initiatives, I’d love to hear from you.

🇺🇸Bradenton, United States$105/hr100% JSS4.73 (34)Since Nov 2017

Earnings and projects

MRR
$32k

Last 6 months ÷ 6

World#54 / 412k
🇺🇸Country#35 / 62.1k
Revenue, last 30 days
$38k

Last 6 months: $191k

World#29 / 412k
🇺🇸Country#17 / 62.1k
Total earnings
$680k

Billed in all: $714k

World#1,398 / 412k
🇺🇸Country#543 / 62.1k
Per project
$11k

$27k in the last 6 months

World#14,427 / 412k
🇺🇸Country#2,455 / 62.1k
Projects, last 6 months
7
14% fixed86% hourly
World#28,826 / 412k
🇺🇸Country#4,152 / 62.1k
Projects in all
63

Across 67 contracts

10% fixed90% hourly
World#48,156 / 412k
🇺🇸Country#7,383 / 62.1k

Earnings, last 30 days

$714k+$37.9k earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$660k$680k$700k$720kOct 8Oct 23Nov 7

Skill rankings: #1 in 9 skills of 15

Rarest: top 0.01% in CRM Software, of 8,314. Ranked by MRR among everyone on Upwork with the skill.

  1. 1CRM Software8,314 freelancers · 🇺🇸 #1Top 0.01%
  2. 1Java8,313 freelancers · 🇺🇸 #1Top 0.01%
  3. 1Jira3,199 freelancers · 🇺🇸 #1Top 0.03%
  4. 1GitHub2,823 freelancers · 🇺🇸 #1Top 0.04%
  5. 1Software QA2,245 freelancers · 🇺🇸 #1Top 0.04%
  6. 1ERP Software1,408 freelancers · 🇺🇸 #1Top 0.07%
  7. 1Atlassian Confluence604 freelancers · 🇺🇸 #1Top 0.17%
  8. 1Operational Planning519 freelancers · 🇺🇸 #1Top 0.19%