JOSH KAPLAN
ENTERPRISE OPERATIONS & TRANSFORMATION EXECUTIVE
Driving scalable outcomes through disciplined execution, modern technology, and responsible AI adoption.
HOW CAN I HELP?
I work with CEOs, boards, and executive teams when technology and AI are critical to enterprise performance, but execution, adoption, or cross-functional alignment has become the constraint.
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With 20+ years operating at the intersection of business strategy, technology, and operations, I help organizations modernize legacy environments, adopt AI responsibly and strategically, and rebuild teams into trusted execution partners. My focus is not on tools or hype, but on governance, sequencing, adoption, and return on investment - ensuring change actually sticks.
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I typically engage as an interim or fractional CXO, or as a hands-on transformation leader during periods of growth, restructuring, or technology-driven change.
INTERIM EXECUTIVE LEADERSHIP
ENTERPRISE AI ADOPTION & ROI
Turning AI into a durable operating capability - not an experiment.
I help organizations move from fragmented AI pilots to governed, enterprise-level adoption that delivers measurable value across people, process, and systems.
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Hands-on leadership when execution matters most.
I step into interim or fractional executive roles to stabilize execution, rebuild leadership capacity, and guide organizations through periods of complexity or transition.
PEOPLE
Building, guiding, and transforming teams through change with clarity and accountability — turning burnout and misalignment into momentum.
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FINANCE
Partnering with leadership on budgeting, planning, and P&L discipline, improving cost visibility, decision-making, and execution through data-driven insight.
PROCESS
Designing and reinforcing operating models and execution rhythms that allow strategy, technology, and teams to move together, especially during growth, restructuring, or modernization.
SALES & MARKETING
Grow your pipeline and bring in new customers, while maximizing profit on your existing customers with a well designed comprehensive strategy.
TECHNOLOGY & OPERATING MODERNIZATION
Modernizing legacy environments, platforms, and workflows in ways that align with how the business actually operates, managing change to reduce risk while enabling future capability.
MERGERS & ACQUISITIONS
​Expert guidance to help find the right company to acquire strategic insights, targeted searches, and support to maximize value and minimize risk.
Josh reported directly to me as Sr Vice President and Market Leader, Northeast Region during my time at Talascend, LLC. He also took on the responsibility for standing up a successful IT practice, building it from inception.
Josh was a true pleasure to work with. He is an exceptional leader of people that assembles the best and brightest in talent and then equips them with the tools and resources they need to achieve the highest levels of success. He brings an entrepreneurial spirit, accountability, and an ownership mentality to his business.
Josh genuinely thrives on tackling operational business challenges head-on with an uncanny ability to quickly create a strategy, assemble the right resources, and execute seamlessly. He is an utmost professional, a great thinker, and truly makes those around him better!
Andrea Hopkey
Transformational Leader
Josh is a delight to work with – he brings that rare combination of exceptional technical smarts and great emotional intelligence. He contributes consistently with great heart and energy to offer focused, thorough solutions and valuable advice. I’ve watched him bring stellar ideas to entrepreneurs to rethink their way to market and ignite their business - helping them identify critical needs to build high-performing cross-functional teams. An impactful, effective leader, Josh guides others to prepare for transformational change with openness, transparency, and enthusiasm.
Karen Benezra
Anti-Defamation League
I’ve known Josh as a confidant and mentor for almost two decades. He’s an incredibly driven, results-oriented leader who sweats the small stuff to make sure his teams can focus on what matters.
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Given his entrepreneurial career path, he’s had a lot of incredibly important roles from IC through C-Level strategic management. His recipe for success is remarkably simple - work harder than everyone else, hire the best people to help, and trust them to help carry the load.
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He’s got deep experience in Sales, Sales Leadership, IT Leadership, and Operations Strategy in several industries such as e-commerce, IT Services, and staffing.
If you’re looking for someone who can course-correct an off-track effort in sales, e-commerce, or general operations, Josh can help you fix it. Or if you’ve got an amazing company that just needs that catalyst to help your growth rate increase - Josh is the best choice! He thrives on responsibility, results, and finding ways to achieve even more over time.