What I Do

I help businesses turn complex initiatives into clear, achievable plans that deliver real results. Whether you're launching a new product, scaling operations, or improving customer service, I bring structure and focus so you can stay aligned with what matters most.With extensive experience in project and program leadership, technical delivery, executive management, and business strategy, I understand how to balance day-to-day execution with long-term strategic goals. I’m hands-on, detail-focused, and committed to keeping you informed with the right amount of insight by raising issues when needed and keeping everything on track behind the scenes.I bring the leadership and experience needed to guide high-stakes enterprise IT projects, solve operational challenges, and drive strategic initiatives. My approach goes beyond technology. I engage stakeholders, build alignment around your definition of success, and help you realize the full value of your investment.Click the video below to see and hear the real person behind this page.

Background

I am a dynamic technology and EPMO leader with over 20 years of experience in project/program management, technology operations, and strategic transformation in healthcare insurance and technology. I am PMP certified, hold an MBA from DePaul University and a Leadership Certificate from the Lake Forest Graduate School of Management. My unique background has served all sides of a program—executive leadership, project execution, and business strategy—enabling a holistic approach to driving success.I have a proven ability to bridge technical and business needs, optimize IT spend, and lead large-scale implementations. I have expertise in cloud operations, security compliance, provider and claims data, financial management, and vendor negotiations. I have hands-on experience with cloud architecture, API design and data management. I've worked for major healthcare payers and a startup, adapting to each unique challenge.I’ve always believed that technology is a tool, not the destination. That belief shaped my path from a teen tinkering with Apple IIs and Atari 8-bit personal computers to a career focused on using technology to drive meaningful business outcomes.I started out supporting servers, networks and desktops then dove headfirst into engineering roles where I soaked up certifications, traveled often while serving diverse clients and I loved every minute. I later moved into Corporate IT at the Blue Cross Blue Shield Association where I helped scale infrastructure, led teams, and discovered the thrill of building systems that matter. Those early days had a startup feel which was fast-paced, hands-on, and full of growth.As the work evolved, so did I. I moved from engineering into project and then program management, drawn to the challenge of turning complex, cross-functional work into something cohesive. I managed multi-million dollar Infrastructure, Security, Data and Software Development programs. I guided Agile transformations, mentored teams, and partnered with business and technology leaders to drive change. Eventually, I transition to Product Director leading a system-wide provider data transformation from the business side.Then came the opportunity to help grow a startup as VP of Technology Operations & Delivery. It brought me back to operations, but with the perspective of a strategist and builder. I drew on everything I’d learned: cloud, security, SDLC, compliance, data, people, and process. We achieved HITRUST certification, matured the company, and built something I’m deeply proud of.The title has changed over the years: Engineer, Operations Manager, Project Manager, Program Director, Product Director, , Vice President but the core has stayed the same. I bring structure, focus, and heart to technical work that enables business success.

4L Data Intelligence Publicity Photo

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2022 Blue National Summit in Orlando

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On Site during Data Center Build in 2006

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Benefit of Working from Home

Services

I bring hands-on leadership to complex, critical IT initiatives, from building delivery structures to turning around troubled projects. I work best in project-based engagements where I can help define and sharpen goals to ensure alignment before execution, or drive delivery on an already clearly defined objective.I’m experienced in delivering both customer-facing and internal initiatives and I will represent your company to the highest standard.

Program & Project Delivery

• End-to-end leadership for new initiatives or in-flight programs

• Turnaround of troubled projects and programs

• Facilitating alignment between executives, stakeholders, and delivery teams

• Refining scope and priorities when direction is unclear

• Operational readiness and go-live execution

• Project audits and post-implementation reviews

• Agile delivery leadership (Scrum Master, Product Owner, Product Manager, RTE)

• Compliance-driven initiatives (SOC 2, HIPAA, HITRUST)

• SDLC projects with significant infrastructure components

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PMO Leadership

• Standing up PMOs or “PMO Lite” structures for fast-growing organizations

• Helping teams clarify priorities and improve focus when competing demands cause drift

• Delivery governance design and execution

• Portfolio-level schedule optimization (including Microsoft Project expertise)

• Executive and stakeholder alignment for large programs

• Mentorship and capability building for PMs and delivery leads

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Infrastructure, Security & Data

• Enterprise infrastructure and cloud platform projects (on-premise included)

• Endpoint protection and security compliance implementations

• Data platform builds and migrations

• Healthcare data (provider, claims) program oversight

• Healthcare analytics platform delivery

• Data governance and regulatory alignment

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Leading Team Discussion

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Even leaders seek guidance from the Wise

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Visiting 4L Data Intelligence Colleagues in Bangalore, India

Experience

Introduction

Over two decades of experience at the Blue Cross Blue Shield Association in different roles has given me a deep understanding of how large enterprises operate and evolve, from infrastructure and operations to strategic programs and business transformation. The variety of roles I held and business areas served provides firsthand insight into how to effectively lead change across organizations.More recently, I led technology operations and delivery at a fast-paced, AI-driven healthcare data startup. There, I applied my experience in technology, security, and compliance to help mature operations under the pressures of rapid growth.Together, these experiences give me the uncommon perspective of enterprise scale and startup agility. This shapes how I lead, deliver, and adapt and how I can help improve your organization.

V.P. Technology Operations and Delivery
4L Data Intelligence (two years)

As Vice President of Technology Operations and Delivery at 4L Data Intelligence, an AI-Powered platform focused on healthcare fraud, waste and abuse prevention and provider data management among other services, I led the company’s IT operations, cloud infrastructure, security and compliance.I led design and implementation of enterprise security and risk management frameworks to ensure data protection and regulatory compliance, including successfully driving the organization through HITRUST certification. I provided hands-on leadership in cloud architecture, infrastructure design, and scalable system security. I managing a $3M+ IT budget to balance performance, innovation, and cost efficiency.I directed both strategic and tactical delivery activities, aligning them with business priorities and timelines. I also oversaw client onboarding and support operations, significantly enhancing the customer experience and service quality.

Program/Product Director (seven years)
Blue Cross Blue Shield Association

This experience uniquely positions me to ensure strong alignment between product and program management, an area where many initiatives struggle. I served as both Program Director (2020–2021) and later Product Director (2022–2023) for a nearly $50M multi-year transformation initiative to modernize and improve data interoperability for a nationwide provider data exchange platform. This rare dual perspective gave me firsthand insight into how strategic delivery and product value alignment must work hand-in-hand to drive success on complex, enterprise-scale programs.From 2018 to 2020, I led a $35M enterprise Data Strategy program spanning multiple related products and dozens of projects. The work was organized into three major workstreams (Claims Data, Provider Data, Master Member Identifier) each coordinated by a Senior Project Manager.I provided leadership, alignment, and accountability across all teams. In addition to overseeing the broader program, I also directly managed select high-impact software development and infrastructure projects. These efforts helped advance the data strategy of the national Blue Cross Blue Shield system and supported member organizations in meeting their evolving business and compliance needs.

Senior Project Manager (twelve years)
Blue Cross Blue Shield Association

I led from project inception to close-out progressively larger and impactful infrastructure, security and software development projects and programs to $3M. I pioneered entrepreneurial project management and managed some of the organization’s first Agile projects and supported agile transformation as an agile coach.

Early Career

I led and performed hands-on technology implementation and support as a systems engineer, operations manager, and project manager focusing on infrastructure, end-user computing, and development support.

Projects

Introduction

The projects featured here span two decades of experience and demonstrate the variety, scale, and impact of the initiatives I’ve led and the depth of experience and knowledge I bring.In many of these efforts, I was responsible for the entire project lifecycle, from justification and funding approval to procurement (RFI/RFP), stakeholder engagement and change management. I led teams from business, technology, vendors and ensured operational handoff.While the specific technologies may have evolved, the fundamentals of leading diverse teams, aligning goals, managing complexity, and delivering results remain constant. It’s this timeless experience that I bring to every engagement.

Program & Portfolio Leadership

Healthcare Data & Analytics

Enterprise Technology & Infrastructure

Finance, Procurement and Compliance

Enterprise Systems & Legal Support

Technology

Introduction

My technical experience allows me to bridge the gap between business goals and technical execution and bring clarity and direction where others might get lost in the weeds. Over the course of my career, I’ve worked across a broad range of technologies and systems.While I may not know from memory every configuration option, I understand what each system is meant to do, how the pieces fit together, and how to support the people making it work. I quickly grasp technical issues, ask the right questions, and can step in to configure or troubleshoot when needed.Whether hands-on or through my teams, I’ve led and supported implementations, migrations, and day-to-day operations across numerous platforms.

Cloud Platforms & Infrastructure
Azure, AWS, Snowflake, Virtual Machines (Windows and Linux), VPNs, Entra ID (Azure AD), Intune, DuploCloudData & Integration Technologies
SQL Server, SnowFlake, Azure Data Factory, Data Stage, data warehouses, REST APIs, interoperability including HL7 FHIRMonitoring & Observability
Azure Application Insights, StatusCake, SolarWinds, Uptrends, custom alerting and loggingEnterprise Productivity & Collaboration
Microsoft 365 (Teams, SharePoint, Outlook, OneDrive), ZoomEndpoint & Identity Management
Entra ID, Intune, Group Policy, device compliance, MFA, conditional accessProject & Work Management
Microsoft Project Server, Planner, Monday.com, AsanaSecurity, Compliance & Risk Management
Proofpoint, Microsoft Defender, HiTrust & SOC 2 controls, vulnerability scanning, Drata, VantaSupport & Service Operations
HubSpot (Helpdesk, Knowledgebase), ServiceNow, email/ticket workflowsSoftware Development & Product Lifecycle
Azure DevOps, GitHub, Jira, Rally, backlog management, release planningBusiness Applications & Enterprise Systems
PeopleSoft Finance, HRIS systems, RFP/RFI tools, vendor portals

Contact

I'm available to collaborate on IT project and program delivery, operational and security initiatives across the U.S.

Let's explore how I can help you solve problems, lead initiatives or free up your time to focus on what matters to you.

Contact me at:

Agent

This assistant is a live demo, created in under an hour to show how AI can provide real-time answers about my background and consulting services.If you're curious about adding something like this to your own site or exploring how AI can support your team, I’d love to help.

AI Enablement & Transformation

Practical AI adoption for real organizations — grounded in delivery, operating models, and leadership.

Introduction

AI is the next large-scale transformation wave — and organizations don’t struggle with the technology. They struggle with the operating model, governance, delivery structure, and cross-functional alignment required to make AI real. That’s the space where I lead.I help organizations move from AI experimentation to practical, scalable capability by applying the same leadership disciplines I’ve used across major cloud, data, security, and product transformations. With deep experience in program leadership, enterprise IT delivery, and regulatory compliance (HITRUST, SOC 2, HIPAA), I guide teams through the complex work of making AI safe, valuable, and operational.My approach combines structured delivery, systems thinking, and hands-on prototyping to help organizations understand where AI fits, how it reshapes the operating model, and what’s required to realize value. I don’t produce academic research or build custom LLMs — my work is grounded in practical application. I make AI operational inside the business by bridging strategy with execution and preparing teams, processes, and governance for what comes next.If you’re looking for an AI partner who brings clarity to ambiguity, aligns stakeholders, and guides the journey from vision to operational reality, I can help.

Value Creation

Realistic AI performance and financial outcomes must be grounded in industry benchmarks, not hype. Studies from McKinsey, Deloitte, Gartner, and MIT consistently show that AI-enabled organizations see double-digit improvements in efficiency, cycle time, and workload reduction — when their operating model, governance, and delivery structure are ready.Actual value varies by organizational maturity, readiness, and openness to change.
I help organizations establish data-driven KPIs and OKRs based on past performance and current capabilities, ensuring AI value is defined, measured, and achieved through disciplined delivery and strong financial rigor.

AI Capability Levels

Modern AI adoption doesn’t follow a linear project phase. Instead, organizations develop capabilities that build on one another to embed AI into strategy, delivery, and operations. These levels describe how AI becomes increasingly integrated into the business — and how leaders can align structure, governance, and operating models to support it.

Level 1 — Exploration & Understanding

Organizations experiment with AI tools, prototypes, and proofs of concept to understand potential value. Work is ad hoc, team-led, and not yet connected to the operating model.Characteristics:

What I help with:
Clarifying realistic use cases, defining initial guardrails, and moving AI from novelty to intentional exploration.Value Creation:

Level 2 — Assisted Delivery

AI becomes part of day-to-day work, augmenting project management, analysis, documentation, and workflow efficiency. Organizations begin building repeatable patterns and early governance.Characteristics:

What I Help With:
Formalizing usage patterns, establishing delivery-aligned governance, and integrating AI into PMO or ITIL workflows.Value Creation:

Level 3 — Integrated Intelligence

AI becomes embedded within processes, platforms, and service delivery. Workflows are redesigned to incorporate AI, driving consistency, scalability, and decision augmentation.Characteristics:

What I Help With:
Operating model updates, cross-domain alignment, and transforming AI from team-level utility to enterprise capability.Value Creation:

Level 4 — AI-Augmented Operating Model

AI becomes a strategic enabler across the organization. The operating model, governance, workforce design, and service delivery structure evolve to fully leverage AI at scale.Characteristics:

What I Help With:
End-to-end operating model evolution, capability scaling, governance modernization, and sustainable enterprise-wide AI adoption.Value Creation:

Framing These Levels for Leaders

These levels are not rigid phases — they represent increasing organizational capability, consistent with PMBOK 8’s performance domains and ITIL v4’s continual improvement principles. Organizations may enter at any level depending on their maturity, strategy, and goals.My role is to help leaders understand where they are today, which capability level aligns with their objectives, and how to evolve toward an AI-enabled operating model that is safe, scalable, and value-driven.

How I Help

I partner with organizations to move from AI experimentation to operational capability — aligning strategy, delivery, governance, and operating models to make AI tangible, safe, and scalable.

Thought Leadership Articles

Introduction

These articles capture my perspective on enterprise transformation in the age of AI—how organizations evolve, how operating models adapt, and what leaders must understand as modern AI systems reshape work. They draw from real transformation experience and connect past technology revolutions to today’s AI-driven shift.Articles are published on LinkedIn and may require login to view the full post. You can browse my latest LinkedIn contributions here: Kyle Ewing's recent LinkedIn Activity (login required).

AI, Technology & Operating Models

AI Generated Project Charter Demo

When an AI "Hallucinates" -- And Why It's Not the Problem People Think it Is

AI, AlphaFold, and Why Your Operating Model Matters More Than Your Models

Building Smarter Programs with RAG: From SOC 2 Documents to AI-Enabled Project Management

Project Management & Delivery Innovation

Three Project Management Aptitudes: Chaos Wranglers, Governors, and Launch Architects

The Unicorn Employee: Redefining IT Project Management Through Diverse Experience

AI and the Talent Shift: Why Cross-Domain Skills Win

Leadership, People & Organizational Behavior

What Your Favorite Sport Says About You

Are All These Layoffs Really the End?

Strategy, Risk & Enterprise Transformation

How to Keep Your Company From Going Bankrupt and Your CEO Out of Jail