Ryan Anderson

ryananderson.net | linkedin.com/in/1ryananderson

I rescue distressed technology programs and build the PMOs that keep them healthy. I have spent eighteen years governing portfolios above $50 million a year and leading global teams that deliver for the C-suite.

  • Executive operations leader
  • Enterprise PMO architect
  • Turnaround specialist
  • Digital transformation executive
Boca Raton, FL. Boynton Beach, FL.
Impact

The numbers first

  • Leadership and scope
  • Results and delivery
  • Technology
  • Community and credentials
  • 18years leading delivery, PMO and operations
  • $50M+annual technology portfolio governed at Connection
  • $5Mcut from annual spend by replacing outside consultancies with internal talent
  • 30%faster delivery of critical projects through standardized product-led agile
  • 60%fewer post-launch production defects after automated regression testing
  • 90days to stabilize a four-year distressed JDE EnterpriseOne rollout
  • 15minutes between automated code promotions at MoreDirect
  • 26%procurement efficiency gain from AI-driven case routing
Experience

Where the work happened

Strategic operations and delivery executive with 18 years of experience building scalable governance frameworks and rescuing highly complex, distressed enterprise initiatives. I bridge the gap between C-suite vision and ground-level execution by establishing product-led agile models, optimizing multi-million-dollar tech budgets and enforcing rigorous financial controls.

FJA

Boca Raton, FL

May 2026 to present

Director of Delivery

  • Oversee all aspects of technology delivery for key enterprise accounts including project management, service delivery, and technical operations.
  • Lead a 93-person global organization of FJA employees and nearshore and offshore contractors across QA, DevOps, Engineering, and Delivery, consolidating accountability for how software is built, tested, released, and supported.
  • Redesign the end-to-end delivery process to make execution more consistent and predictable across accounts.
  • Build a delivery management department, defining its structure, roles, and governance.
  • Drive high-impact project execution and align global delivery strategies with long-term business objectives.
  • Mentor and develop staff, fostering a culture of accountability, collaboration, and continuous improvement.

Connection

Merrimack, NH (hybrid)

2021 to 2025

Vice President, Program Management Office

  • Built and scaled an enterprise-grade PMO from the ground up, directing a global team of 20 senior delivery professionals to govern an annual technology portfolio exceeding $50 million.
  • Engineered the rapid turnaround of a severely distressed, four-year JDE EnterpriseOne ERP rollout, successfully stabilizing collapsing procurement and invoicing operations within a 90-day recovery sprint.
  • Facilitated overarching corporate strategy by establishing an Executive Steering Committee (ESC) and Change Advisory Board (CAB), guiding C-level executives in prioritizing and funding high-impact technology investments.
  • Slashed annual operational expenditures by $5 million by strategically displacing high-cost external consultancies with internal talent, consolidating IT service management, and driving aggressive cloud adoption.
  • Standardized software development life cycles and product-led agile frameworks across integrated business units, successfully accelerating critical project delivery timelines by 30%.
  • Deployed advanced AI-driven case routing mechanisms, generating a 26% efficiency boost in procurement workflows while maintaining strict financial compliance.

MoreDirect

Boca Raton, FL

2008 to 2021

Senior Director, PMO, DevOps, Quality Assurance, and Customer Success

2013 to 2021

  • Commanded a diverse, 24-person cross-functional organization spanning project management, infrastructure automation, quality assurance, and client operations.
  • Drove a 48% surge in feature deployment velocity over 18 months by championing Scaled Agile Framework (SAFe) principles and optimizing engineering structures.
  • Radically modernized software delivery by architecting fully automated CI/CD pipelines, enabling the reliable promotion of application code every 15 minutes.
  • Overhauled enterprise quality assurance protocols, instituting robust automated regression testing that plummeted post-launch production defects by 60%.
  • Mitigated organizational risk by 25% and maintained stringent SOX regulatory compliance through the implementation of structured executive governance boards.
  • Designed and launched comprehensive customer success playbooks from scratch, utilizing data-driven health dashboards to proactively accelerate client time-to-value and boost retention.

Director, Program Management Office

2010 to 2013

  • Founded the organization's inaugural PMO, transforming disparate departmental efforts into a highly disciplined, strategically aligned delivery engine.
  • Boosted overall portfolio success rates by 35% through the introduction of rigorous stage-gate controls, milestone tracking, and executive performance reviews.
  • Directed sweeping information security initiatives, successfully guiding the enterprise through complex PCI DSS and SOC2 Type II compliance audits.

Senior Project Manager

2008 to 2010

  • Expedited business-to-business client onboarding processes, drastically reducing integration durations from multiple hours to just three minutes.
Skills

Competencies and tools

Executive leadership

  • Strategic Planning
  • Portfolio Governance
  • C-Suite Alignment
  • Financial Management & Capitalization

Delivery & operations

  • Scaled Agile (SAFe)
  • PMO Architecture
  • Turnaround Strategy
  • Change Management
  • CI/CD Pipeline Automation

Enterprise tech

  • Cloud Migrations (AWS/Azure)
  • ERP Implementations (JDE E1)
  • IT Service Management (ServiceNow)
  • Portfolio Management (Planview, Jira)
  • Data Analytics (Power BI)

Delivery & governance tools

  • Jira
  • Planview
  • ServiceNow (ITSM/CMDB)
  • MS Project
  • Smartsheet

Cloud & architecture tools

  • AWS (EC2, RDS)
  • Kubernetes
  • Docker
  • Terraform
  • Ansible

Business systems & automation tools

  • Salesforce
  • SAP Ariba
  • Pega
  • Python
  • Jenkins
  • Power BI
  • EducationBusiness AdministrationFlorida Atlantic University
  • CertificationCertified Scrum Master (CSM)Winnow Management
  • CertificationCertified Scrum Product Owner (CSPO)Winnow Management
About

Off the clock

Beyond my professional life, I am proud to call Boynton Beach home, where I live with my wife, our son, and our cats. I firmly believe that strong leadership extends beyond the boardroom and into the community. Since 2013, I have served as President of my local Homeowners Association, overseeing annual budgets and guiding capital improvement initiatives for our neighborhood.

When I am unplugged from technology and transformation projects, you will almost always find my family on the water. I am an avid boater and saltwater angler, and we spend our weekends fishing, snorkeling, and exploring the Florida coast. Back on land, I enjoy actively supporting my son's youth sports and scouting events, tinkering with custom web development and AI tools, and firing up the kitchen to cook for large gatherings of family and friends.

Thanks for stopping by. Whether you want to discuss enterprise strategy, community building, or swap a great recipe, I would love to connect.

Contact

Let's talk

Let's connect to discuss how I can help optimize your operations and drive predictable growth.

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Thank you! I'll get back to you as soon as possible. Wishing you a wonderful day!

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