Chall Montgomery
Vice President | Enterprise Architect - Driving 30% Vulnerability Reduction, 1.2M Cost Savings, Zero-Trust & AI/ML-Powered Enterprise Security
- Role
- Founder & Chief Executive Officer at Challgorithm
- Location
- Cleveland, OH, US
- LinkedIn followers
- 500 followers
About Chall Montgomery
As the Founder & CEO of Challgorithm, an AI automation and enterprise consulting…
Experience
Founder & Chief Executive Officer
Oct 2025 — Present · Cleveland, OH, US
Founder & CEO of Challgorithm, an AI automation and enterprise consulting firm that helps organizations modernize operations, eliminate inefficiencies, and scale through intelligent workflow automation and AI-driven systems.I partner with executives, operators, and founders to design and implement practical AI solutions. Focused on measurable business outcomes, operational leverage, and long-term scalability.Core Responsibilities & Impact: • Lead company vision, AI automation strategy, and enterprise client delivery • Architect end-to-end AI-powered workflows across operations, recruiting, finance, and customer experience • Advise leadership teams on digital transformation, operating models, and automation roadmaps • Design no-code, low-code, and custom AI solutions using modern automation stacks • Translate complex business problems into scalable, data-driven systems
Education
Walsh University
Bachelor of Arts (B.A.)
2013 — 2016
United States Naval Academy
Economics
2011 — 2013
Western Governors University
Master of Business Administration - MBA
2025 — 2026
Southern New Hampshire University
Master of Science - MS
2019 — 2021
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