In business and in life, my philosophies are firmly rooted in my rural Missouri upbringing and time as an All-American wrestler. Whether leading a high-tech organization or scaling a non-profit, I attribute much of my and my teams’ success to this foundation, which I still draw from today.
My story began in the small town of Maryville, Missouri. As a high-school All-American wrestler, I recorded an unprecedented 63 wins and 0 losses. We won the state championship in both 1994 and 1995, after which I was offered wrestling scholarships by seven Midwest wrestling programs, ultimately deciding to attend Blair Academy on an Army (West Point) scholarship.
A senior year shoulder injury prevented me from attending the U.S. Military Academy, but I was fortunate to be accepted to Brown University where I also served two years as Captain of the Wrestling team. My time as Captain was an incredible learning experience. This was one of the earliest opportunities I had to try my hand at leadership. Not only did I find out how rewarding it was to be involved in building something larger than myself, but the lessons I took from that time have yet to fail me in the business world. Thanks to the inspiring team around me, I was ultimately awarded the Cliff Stevenson Outstanding Leadership Award for my contributions off the mat.
After college, I briefly dabbled in the world of investment banking and private equity, quickly realizing that I had more of a passion for entrepreneurship and creating things. So, in 2002, I founded and launched my first company, ConnectEDU.
My new challenge is AutoReturn, where I became chief executive in 2022. Later that year, we acquired Joyride, an e-commerce marketplace for impounded vehicles. 2023 saw the relocation of corporate headquarters from San Francisco to Boston, an expanded management team and our new brand identity: Autura.
As we plan on doubling our workforce over the next year, my “dogsled style” of leadership means it’s time for me to get out of the way and let them run.
In 2013, I joined a legacy milage reimbursement company called Corporate Reimbursement Services (CRS). Although it had the trappings of a staid business, I saw growth potential in the market and its products. As president and CEO, and along with my core management team, we realigned the business and rebranded as Motus, built and fostered a winning culture, and transitioned CRS from a tech-enabled services company into a true SaaS platform. In 2018, we partnered with Thoma Bravo to accelerate growth, drive industry consolidation, and dramatically expand our addressable market through a combination of innovation and M&A.
Knowing first-hand how daunting it can feel to climb from modest roots to the corporate world, I created ConnectEDU with the vision of providing access to critical college and career planning resources for students of all-income levels, regardless of their ability to pay. I spent approximately 11 years with ConnectEDU, growing it into the world’s largest education network. In that time, my team and I achieved significant revenue growth and amassed more than 20 million proprietary student records, servicing over 5,000 K-12 districts, hundreds of colleges and universities, 130,000 employers, and numerous state-funded school-to-career-to-education pathway platforms.
The ConnectEDU journey invigorated me for a new chapter.
Outside of Autura, I serve as Chairperson Emeritus for the Special Operators Transition Foundation (formerly Your Grateful Nation). I’ve helped the organization rapidly scale, expand its employment ecosystem of hiring partners, and achieve a 20%+ year-over-year increase in successful Fellow transitions for former elite United States Military warriors.
True to my wrestling background, I also serve as Chairperson of the Board of Directors for Beat the Streets Foundation. In my time with the organization, we’ve created and successfully merged two powerhouse regional wrestling programs into Beat the Streets New England, growing opportunities for wrestling-based youth development with intentional programming and mentoring throughout the region.
In my decades of driving high-growth companies and leading winning teams, I’ve developed a proprietary methodology for vision alignment and performance optimization that has proven successful time and again in business and philanthropic organizations. I’ve been fortunate to share these lessons as a featured speaker at several industry events, as well as through my regular contributions to outlets such as Inc., Entrepreneur, Forbes, and InformationWeek.
Beyond my passion for leadership and coaching, I’m a lover of country music and “all things” bar-b-q.
Craig has received numerous industry accolades for his leadership, including a Cliff Stevenson Award for Outstanding Leadership, Executive of the Year by the Best in Biz Awards International, and multiple Stevie Awards for Executive of the Year.
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