About The CIO Project
The CIO Project was born from a simple observation: the technology leadership space was filled with sanitized corporate content, but lacked the authentic, unfiltered conversations that actually drive meaningful change. We created this podcast to fill that gap with "Confessions; Real Talk; Real Tech."
Our Mission
"To create a space where technology leaders can have the conversations that matter most - the ones that happen behind closed doors, filled with real challenges, honest failures, and hard-won wisdom."
What We Stand For
Our approach to technology leadership conversations is grounded in these core principles.
Authentic Conversations
We believe the best insights come from honest, unfiltered discussions about real challenges and experiences.
Peer-to-Peer Learning
Our content is by technology leaders, for technology leaders - creating genuine value for our executive audience.
Community Building
We're fostering a community where current and aspiring IT leaders can learn, connect, and grow together.
Actionable Insights
Every conversation aims to provide practical wisdom that listeners can apply in their own leadership journey.
Meet Your Hosts
Two industry veterans who bring decades of real-world experience and complementary perspectives to every conversation.
Howie L Lyke
CEO & Veteran IT Strategist
Sherpa Techs LLC
With nearly four decades of IT leadership strategy experience, Howie brings unparalleled insights into technology transformation and executive leadership. His career spans multiple industries and organizational transformations, making him one of the most respected voices in enterprise technology strategy.
Key Achievements
- CEO of Sherpa Techs LLC
- Led digital transformations for Fortune 500 companies across multiple industries
- Pioneered innovative IT governance frameworks adopted by major corporations
- Mentored dozens of emerging CIO leaders throughout his career
- Expert in enterprise architecture and strategic technology planning
Brian Shield
SVP, CTO & CIO
Boston Red Sox
Brian serves as the SVP, CTO & CIO of the Boston Red Sox and National Chair of InspireCIO, bringing cutting-edge technology leadership to both sports entertainment and the broader IT community. His unique position at the intersection of sports, technology, and fan experience provides fascinating insights into modern technology challenges.
Key Achievements
- SVP, CTO & CIO at Boston Red Sox
- National Chair of InspireCIO organization promoting IT leadership excellence
- Champion of diversity and inclusion in technology workforce development
- Expert in fan experience technology and sports industry digital transformation
- Recognized leader in applying enterprise technology to entertainment industry
Why We Started This
The CIO Project emerged from countless conversations between technology leaders who were hungry for something different. Too many industry events featured the same polished presentations. Too many podcasts stuck to safe, corporate-approved talking points. Meanwhile, the most valuable learning happened in informal settings - over coffee, during networking breaks, or in those honest moments after the official presentation ended.
Howie and Brian recognized this gap and decided to create the podcast they themselves wanted to listen to. A show where a CIO could admit that their last digital transformation didn't go as planned. Where a CTO could share the leadership lessons they learned from their biggest failure. Where real challenges get real discussion, and where the audience consists of peers who understand the weight of technology leadership decisions.
The "beverage in hand" ethos isn't just about creating a relaxed atmosphere - it's about acknowledging that the best business conversations often happen in informal settings where people can be genuinely themselves. That's the environment we're recreating in audio form, one conversation at a time.
Join the Conversation
Ready to be part of a community that values authentic leadership discussions? Start with our latest episode and discover what real talk sounds like.