Ray Healy, a dynamic and competitive sales leader, joins Chief Outsiders to scale enterprise security, premium CPG, and transportation solutions companies as a fractional CSO.
DENVER, COLORADO – October 28, 2025 – Ray Healy, a dynamic and competitive leader with a history of successful sales leadership in private equity-backed organizations, will know apply his extensive security, premium CPG, and transportation industry knowledge to take client sales to the next level as a Fractional CSO for Chief Outsiders. Recently, Healy joined Chief Outsiders' team of more than 120 Fractional Chief Sales Officers (CSOs) and Fractional Chief Marketing Officers (CMOs).
“Recognized as an innovator with expertise in driving organizational performance, Ray enhances productivity, maintains high quality standards, and fosters excellent organizational skills,” said Karen Hayward, Managing Partner, Chief Outsiders. “We are thrilled to add his deep security industry experience to our team of battle-tested CSOs.”
According to the Chief Outsiders website, Healy demonstrates strong analytical abilities and excels in leading high performing teams within complex organizational structures. Equipped with vision, an extensive track record of leadership, and proven results, he leverages excellent communications skills to influence operational performance and maximize results.
Security Solutions Sales Leadership
At Chief Outsiders, Healy works with the CEOs of PE-backed, early-stage, and mid-market security technology companies to accelerate sales growth. Whether delivering global revenue growth or building organizations for successful exit, his focus is on maximizing sales performance.
Prior to joining Chief Outsiders, as Chief Revenue Officer at Tarian, an enterprise security solutions company, he delivered $47 million in revenue, exceeding the budget by 42% by spearheading the development of a comprehensive growth strategy. He also built and sold a successful start-up organization closing at a 15x multiple.
Healy’s executive sales leadership experience also includes roles as SVP, Client Development/CCO at Arctic Glacier, Inc., VP/GM National Account Sales for U.S. Security Associates, Inc, and RVP, Southwest at NBSL, Inc. Prior roles include Vice President National Accounts at U.S. Security Associates, Inc., President for Inspiratranz, LLC, and Region Vice President at Securicor.
To support his successful sales leadership career, Healy earned a B.S. in Business Administration with an emphasis in Finance from San Diego State University, in San Diego, California. He also holds a Certified Personnel Consultant (CPC) Certification from the National Association of Personnel Services.
About Chief Outsiders
Mid-sized companies unlock market potential and accelerate growth with top-tier talent and technology from Chief Outsiders, the nation’s leading provider of fractional sales and marketing services.
CEOs and business leaders drive sales and marketing strategy to make big things happen with instant access to the firm’s cohesive, battle-tested team of more than 120 fractional executives, a diverse pool of world-class expertise. Each brings the experience of VP Sales, VP Marketing, or higher at one or more operating companies, including many Fortune 500 firms.
Team OutsidersTM leverages this same expertise to deliver on-demand enterprise-grade execution to power growth with efficiency and flexibility. GrowthGearsSM OS supports faster, smarter, and less risky growth. The industry’s first AI-powered growth platform integrates both the comprehensive strategy of fractional executives and the precise execution of Team OutsidersTM. We built its transparent, client-friendly interface around Chief Outsiders’ proven Growth GearsTM process.