Rob Calloway

Focus Areas

  • Executive Leadership
  • Digital Strategy
  • Software Delivery and Product Development


  • BS Aerospace Engineering, Notre Dame
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Rob has over 30 years of consulting and industry experience.  He has lead global practices for multiple top consulting firms, which included building out go to market strategies, developing the people and culture for growth, and owning a P&L.

Rob has consulted for many of the top global brands and companies across industries covering retail, consumer packaged goods, financial services and insurance, health care, automotive and manufacturing, energy and utilities, communications and life sciences. He brings a deep and relevant outside-in perspective in helping clients and c-suite executives refine their vision and define their digital strategy to maximize their ROI. His background and leadership show exceptional performance in building a consulting practice and managing client relationships. Rob’s Technology experience includes a broad set of emerging technologies, which helps him articulate new and innovative digital solutions for clients.  Rob has built practices across several platforms and technology organizations, and he has relationships with the top software technology firms across the industry.

Rob is a senior advisor for Cuesta, and he believes in the value technology can unlock across organizations and Cuesta’s unique ability to drive digital change in today’s accelerating world.  

Rob has 4 grown children and lives with his wife in Tampa Bay.  When he’s not working, he and his wife can be found enjoying the day on the water.