Jason Richard is a digital technology executive with more than 20 years of experience leading technology organizations, transformation programs, and high-change business initiatives.
His career has focused on moments when companies need technology leadership that is practical, fast-moving, and business-minded. He has led technology carve-outs, built IT organizations from the ground up, modernized legacy platforms, launched digital capabilities, supported international expansion, and helped companies reduce risk while improving execution.
Jason currently serves as Chief Technology Officer at Lemonaid Health, where he leads technology strategy for a nationwide telehealth and digital pharmacy platform. He is also the founder of CIO Response, a boutique advisory practice focused on fractional CIO, CTO, and CISO leadership, technology diligence, carve-outs, and transformation execution.
His prior leadership roles include Leslie’s, Lucky Brand, Williams-Sonoma, Infosys, and Accenture.
Jason’s leadership style is direct, collaborative, and outcome-oriented. He is comfortable operating at the executive and board level, but he also believes effective technology leadership requires staying close enough to the work to understand the real constraints, tradeoffs, and opportunities.
He is known for connecting technology strategy to business priorities, building strong teams, simplifying complex problems, and creating the operating discipline required to move from plan to execution.
Many technology leaders are most comfortable in stable environments. Jason’s background is different. He has repeatedly led technology through disruption, transition, and reinvention.
That includes standing up new technology organizations, separating companies from parent organizations, replacing legacy platforms, improving vendor models, strengthening delivery performance, reducing operational risk, and helping companies create technology foundations for the next phase of growth.
• Technology transformation
• Investor-backed company transitions
• Carve-outs and divestitures
• Digital commerce and customer experience
• Healthcare technology and telehealth platforms
• Retail systems, field service, and omni-channel operations
• Security, compliance, and risk management
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