In October, RoleModel announced the promotion of Caleb Woods from Software Director to Chief Technology Officer. I’d like to share a bit more about Caleb than what’s in the press release, as his journey is not your mainstream CTO’s journey.

Unique Education

Caleb was homeschooled by parents who were active in the Michigan homeschooling community. His father, John, is a mechanic. His mother, Miriam, is an Accountant. So, in addition to learning the 3 R’s, he learned a lot of things most pre-college students never do. He learned how things worked, whether cars, organizations, or money. He also participated in a lot of competitive team sports.

Caleb started working in a financial consulting firm while still in high school. While at the firm, he learned about spreadsheets and other technologies used by the financial firm. His programming experience began here, customizing CMS plugins and writing a bit of JavaScript.

Having an “outside of the box” education to that point, he decided to get his college degree in Computer and Information Technology through an accelerated program as part of CollegePlus. As he interacted with the people at CollegePlus, they were impressed with him enough to offer him a job. He moved to Washington state and started in the office.

Building IT Infrastructure and Growing a Software Team

Soon Caleb began working as a liaison to a group to which CollegePlus had outsourced some software development. He identified some inefficiencies and ineffectiveness in the approach of the outsourced team. As he began learning more about software development himself, he questioned their technology choices and the code itself. Eventually, he was moved to the IT organization to develop some of CollegePlus’s internal software systems and moved to San Antonio.

When Kevin Bridges joined CollegePlus as the Director of IT, he contacted me to get some advice about how to grow their IT organization with an emphasis on developing their own software for some of their proprietary systems. (I had not yet met Caleb at that time, but knew some of CollegePlus’s founders). Sitting on a proposal from Caleb, and adding the small amount of advice from myself, Kevin convinced CollegePlus to embark on both a development plan and a Software/IT apprenticeship program.

In a very short period of time, by industry standards, CollegePlus internal systems were working with a single-sign-on service, and they had developed some pretty talented young software developers. After some management and other internal changes were made, Caleb decided to pursue a career that would combine what he had learned to help solve business problems by leveraging Software/IT. He joined RoleModel Software as a Software Developer/Consultant, moved to North Carolina and started the next phase of his life with his new bride, Kimberly.

Applying His Skills as a Software Developer and Consultant

Caleb’s first assignment in 2012 was to work with me on a pretty advanced project building a cloud-based data storage service for the Agricultural industry. He quickly picked up the work that was done so far and took it to the next level. Not only did he significantly advance the technology, but he also became the leader of the project and served as the liaison to new efforts to migrate an extensive amount of historical data stored on PCs to the new system, and supported two new client platforms of the services that were built and evolving.

After several other successful assignments, he led a technology transformation for another large client providing both technical and team leadership. Recognizing his amazing leadership skills, he became a “member at large” on the leadership team of RoleModel. While in this position, Caleb provided great insights and initiated some applications of technology to streamline our operations. He did this all while continuing to provide great leadership at our large client.

Growing as a Leader

In early 2016, Caleb was named Software Director at RoleModel, becoming a major interface to new clients, an influencer of technology choices and practices, and mainly responsible for the health of the environment among the software team. He jumped in with both feet, carefully innovating while making sure there were tight feedback loops on any experiment whether internal or client-facing. He continued to take on more and more leadership.

I couldn’t be more excited to have Caleb take on this new position as Chief Technology Officer, where he will be leading the full set of technology services RoleModel provides. He is a visionary-integrator, a man of character, and a pleasure to work alongside whether as a mentor, mentee, or peer.

Caleb is a “roll up your sleeves” kind of leader. He doesn’t just talk about it, he gets things started, sees them through, and everyone around him grows while he’s doing it. We chose the name “RoleModel” knowing it was a high bar. Caleb continues to clear it.