Caleb Walker

Caleb Walker has a diverse work experience that spans from 2001 to the present. Caleb held multiple roles and positions in various companies and organizations.

In 2001, Caleb joined the Canadian Armed Forces as a Canadian Army Officer. Throughout their military career, they served in roles such as Task Force Commander, where they led a team responsible for the security of the Canadian Ambassador in Afghanistan. Caleb also contributed to the development of the Canadian Armed Forces' digital strategy and conducted reviews of the Army's Managed Readiness System. Caleb retired from the Canadian Army as the Commander's Initiatives and Action lead in 2021.

In 2014, Caleb founded Walking Forward Development, a real estate holding company. The company grew from a single assumed mortgage to managing dozens of units across Canada. Currently, Walking Forward Development offers advisory services to private and non-profit property-focused organizations.

Starting in April 2020, Caleb worked at WithYouWithMe, initially as the Country Manager. Under their leadership, the team grew from one employee to 140, and the company's annual revenue increased from zero to $19 million. Caleb later became the SVP of Strategic Development, contributing to the company's growth and success.

In 2023, Caleb founded The Digital Insurgency, where they continue to challenge the status quo and drive a reformist digital insurgency. With their background as an ex-Army professional and a tech strategist, they aim to empower organizations and individuals to embrace digital transformation.

Overall, Caleb's work experience showcases their leadership abilities, strategic thinking, and entrepreneurial spirit across different industries and organizations.

Caleb Walker's education history includes a Bachelor's degree in Political Science and Government from the Royal Military College of Canada/Collège militaire royal du Canada, which they obtained from 2001 to 2005. Caleb then pursued a Master's degree in War Studies from the same institution, completing it from 2008 to 2012. Caleb also attended the Royal Military College of Canada/Collège militaire royal du Canada from 2012 to 2013, focusing on Professional, Technical, Business, and Scientific Writing. Lastly, they pursued a Master of Arts degree in International Relations and National Security Studies at Massey University from 2017 to 2018.