Ryan Anderson

Intro

Welcome!

I’m a results-driven executive leader with a passion for program management, business transformation, and technology leadership. With a track record of building and scaling PMOs, managing large portfolios, and driving change management automation, DevOps, and agile adoption, I thrive at the intersection of strategy and execution.

My expertise lies in solving complex business challenges, optimizing processes, and leading high-performing teams to deliver impactful outcomes. Whether it’s implementing enterprise-wide initiatives, fostering innovation, or driving organizational change, I bring a practical, results-oriented approach to every challenge.

Let’s connect and explore how I can help transform your business.

Work

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Vice President, Program Management Office

Led a high-performing, globally distributed team of project management professionals, driving strategic alignment and execution across the organization. Partnered with C-suite leadership to establish corporate operating cadences, including goal setting, forecasting, KPI reviews, and executive business reviews to align technology and business priorities.

• Spent significant time directly managing C-suite priorities and alignment, acting as a trusted advisor and moderator for enterprise strategic direction.
• Created and led the company’s Executive Steering Committee (ESC), facilitating quarterly strategy sessions with C-level executives and division presidents to set and refine company-wide priorities.
• Moderated strategic debates, driving consensus on short- and long-term actions that guided all staff.
• Delivered monthly updates to senior leadership on execution progress against ESC-ranked priorities, ensuring accountability and clear progress tracking.
• Hosted monthly Change Advisory Board (CAB) sessions with all VPs and their designated directors to evaluate, approve, and rank new initiatives, verifying alignment with strategic objectives and capacity.
• Produced executive IT materials for the CIO’s quarterly Board of Directors presentations, ensuring clear communication of program value and progress.
• Built and scaled the Program Management Office (PMO) from the ground up, establishing a formalized PMO and growing a team of 10-23+ senior-level Project Managers and facilitators to manage strategic enterprise-wide initiatives.
• Managed a $50M+ annual portfolio, implementing a governance framework that improved program transparency, financial oversight, and prioritization of high-impact initiatives.
• Established and institutionalized a Software Development Life Cycle (SDLC) and Agile governance framework across multiple merged business technology units, reducing project delivery time by 30%.
• Spearheaded enterprise-wide process optimization, automating business workflows and enabling scalable growth. This included managing execution of a centralized data governance model.
• Defined and monitored Key Performance Indicators (KPIs) and Objectives and Key Results (OKRs) to assess program success and optimize business impact.
• Championed change management initiatives during enterprise-wide technology transitions, ensuring seamless adoption and minimal disruption.
• Mentored and provided leadership to PMO team members, fostering professional growth and enhancing program execution capabilities, driving a 10% increase in strategic success.

• Led multiple ERP implementations and enterprise system integrations (JDE EnterpriseOne, CRM, CPQ, WMS, ITSM, CMDB, AI/ML, API), ensuring seamless transitions for Fortune 500 customers and enhancing operational efficiency.
• Implemented analytics and BI tools (Power BI, Domo) to enhance KPI tracking, performance monitoring, and decision-making across operations.
• Orchestrated design and implementation of AI automation for case management (using Pega), resulting in a 26% increase in operational efficiency for procurement and automated approval workflows, reducing processing time for capital and operational expenses while ensuring compliance.
• Championed cost optimization initiatives, reducing IT expenses by $5M annually through cloud migration, automation, and ITSM & CMDB consolidations.
• Developed and deployed a financial controls framework to enhance project cost tracking and capitalization efforts, ensuring proper classification of labor costs and accurate billing for contracted resources, reducing unbilled expenses and strengthening financial oversight.

Sr. Director — PMO, DevOps, QA, & Customer Success/Application Support | 2013 - 2021

Led a 24-person cross-functional team across Program Management, DevOps, Quality Assurance, and Application Support, driving program delivery and support for Connection’s Enterprise division. Directed technology strategy and execution to deliver rapid, reliable digital solutions, spearheading large-scale cloud adoption and customer success for Fortune 1000 clients.

• Increased change request deliveries by 48% within 18 months through SAFe implementation and Agile education.
• Enhanced cross-functional collaboration, bringing transparency to prioritization, development, testing, and release processes.
• Implemented structured governance (CABs, Executive Steering Committee), reducing change-related risks by 25% and ensuring SOX compliance.
• Chaired Executive Steering Committee, leading change governance to reduce risk and ensure SOX compliance.
• Provided leadership and mentorship to PMO team members, fostering professional growth and enhancing program execution capabilities.

• Accelerated API adoption, delivering MVP endpoints within 10 months and achieving full adoption in 4 months.
• Built real-time REST API integrations with ServiceNow ITSM and CMDB, reducing cXML implementation time from 5 hours to a 3-minute self-service model.
• Optimized engineering structure and reorganized staff, increasing development efficiency by 30%.
• Re-architected and deployed a high-traffic web application within 12 weeks, achieving highest development velocity and eliminating contracted resources.
• Architected and migrated infrastructure to AWS, implementing infrastructure-as-code (IaC) with Ansible and Terraforms for automated, synchronized environment configurations.
• Developed a fully automated CI/CD pipeline using Python, Jenkins, Ansible, and Gerrit, enabling application code promotion and reversion (based on automated tests) every 15 minutes.

• Revitalized Quality Assurance into an automation powerhouse, significantly enhancing testing efficiency and code quality.
• Reduced production defects by 60% through the implementation of automated regression testing and Behavior-Driven Development (BDD) methodologies, which also improved code reliability and deployment speed.
• Increased QA team output by 23% and reduced detected bugs by 11% prior to automation initiatives; subsequently, shipped product quality improved by 60% post-automation.
• Created and trained a multi-tiered QA team to perform sprint-focused manual testing complemented by automated regression, utilizing Java, Selenium, Gherkin, Cucumber, TestNG, and test mapping, with execution and reporting managed via Jenkins, TestNG Results plugin, and Allure Jenkins plugin.

• Built and scaled Customer Success from the ground up, creating workflows, playbooks, and success plans that accelerated time-to-value and enhanced client satisfaction.
• Leveraged data-driven dashboards and analytics to monitor customer health, identify adoption gaps, and enable proactive engagement that boosted retention.
• Owned all technical aspects of RFP (Request for Proposal) responses, which included architecture, integration planning, security posture, and BCDR (Business Continuity and Disaster Recovery) strategies.
• Ensured that proposed solutions within RFP responses aligned with stringent client and regulatory requirements, thereby securing scalable and compliant outcomes.
• Integrated Application Support into development, ensuring early issue identification and knowledge transfer, reducing upfront training time and production escalations.

Director — PMO     2010 - 2013

As Director of the Project Management Office at MoreDirect, I was responsible for building and maturing the PMO from the ground up, transforming it into a strategic driver of execution and alignment across the business. My efforts focused on implementing standardized governance, optimizing processes, and accelerating high-priority programs to support company growth and scalability.

• Established and scaled the company's first PMO, leading governance transformation to drive digital and creative program execution.
• Implemented standardized project governance, introducing stage-gate controls and formalized intake and prioritization processes that brought clarity, accountability, and improved transparency to portfolio delivery.
• Introduced Agile and hybrid delivery frameworks to support both product and infrastructure teams, reducing time-to-value by 30%.
• Increased project success rates by 35% by launching milestone tracking and executive reviews tied to delivery and KPIs.
• Drove execution of enterprise-wide projects, including system upgrades, cloud migrations, and automation efforts, ensuring consistent delivery discipline and measurable outcomes.
• Developed and managed executive dashboards and portfolio reporting that improved stakeholder engagement and elevated risk visibility at the portfolio level, enabling executive leadership to make faster, better-informed decisions.
• Owned SOX audit readiness and execution for the IT organization, aligning project controls, access management, and change procedures to ensure full compliance and successful audit outcomes.
• Reduced cross-functional delays by 20% by implementing a unified delivery framework and formalizing cross-departmental dependencies, accelerating high-priority project throughput.
• Partnered with legal, infrastructure, and security teams to ensure technical proposals met enterprise standards and client requirements.
• Acted as a key escalation point and senior advisor for cross-functional project delivery teams.

Sr. Project Manager — PMO     2008 - 2010

Led high-impact client integrations and B2B platform enhancements that streamlined onboarding, improved product discoverability, and supported revenue growth. Worked cross-functionally with sales, engineering, and product to deliver faster, more scalable solutions.

• Delivered the industry’s fastest ERP tool integration, reducing client onboarding from five hours to three minutes.
• Rebuilt B2B search engine to boost discoverability and scalability.
• Partnered cross-functionally to deliver solutions aligned with client revenue goals.
• Acted as a primary client liaison for complex integrations, ensuring clear communication, issue resolution, and on-time delivery for mission-critical B2B partnerships.

Project Manager > Sr. Project Manager

• Led cross-functional teams to deliver complex hosting and billing platform projects for enterprise clients including eBay, AOL, Comcast, and Costco, accelerating delivery timelines by up to 50%.
• Managed stakeholder communications, technical scope, and integration planning to ensure successful launch and adoption of high-impact systems.
• Directed the migration of 1.2M live customer accounts with minimal downtime and churn.

About

Hi, I’m Ryan, and I call South Florida home. I’m lucky to share this beautiful life with my amazing wife and our wonderful son. Our family wouldn’t be complete without our playful orange & white cat, who keeps us on our toes!

We love spending time on the water—whether it’s fishing, snorkeling, or tubing behind the boat, there’s nothing better than soaking up the sun and making memories together. Family means everything to us, and we’re grateful to be close with our parents and siblings, sharing traditions, laughter, and plenty of weekend get-togethers.

Thanks for stopping by, I’d love to chat!

Contact

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