Executive Bio: Bailey Caldwell
Senior Technology Executive • 30+ Years Experience • Transformation Leader
Bailey Caldwell is a senior technology executive with more than three decades of experience building practices, scaling organizations, and delivering measurable transformation across SaaS, cloud, and digital platforms. His career spans leadership roles in global consulting, enterprise software, and high-growth digital businesses, giving him a rare combination of consulting rigor, enterprise execution, and consumer internet scale.
McKinsey & Company Leadership
At McKinsey & Company, Bailey helped found the Cloud by McKinsey practice and went on to create and lead the firm's Technology Economics and FinOps practice. He built McKinsey's capabilities in technology financial governance, IT economics, and cloud cost optimization—enabling Fortune 1000 clients to bend cost curves, accelerate transformation, and embed financial accountability into technology strategy. His work influenced CxO-level technology adoption and procurement frameworks across industries. Bailey also served as a Governing Board Member of the FinOps Foundation (2021–2023), helping define global standards for technology financial management.
Enterprise Software & Cloud Transformation
Before McKinsey, Bailey held senior executive roles at Flexera and RightScale, where he scaled global pre-sales, solutions engineering, and customer success organizations. He became known for "accelerating the technical yes," creating operating models and playbooks that increased win rates and shortened deal cycles. At RightScale, he also built one of the world's most successful cloud partner ecosystems, forging deep alliances with Google, Amazon, Microsoft, and IBM, and enabling global enterprises to adopt and optimize cloud services.
SaaS Business Model Innovation
Earlier in his career, Bailey joined Paxonix, where he led one of the earliest SaaS business model transformations. He built product and delivery capabilities for an enterprise SaaS platform that attracted leading CPG clients and fueled revenue growth during a critical stage of adoption.
He then served as an executive at Realtor.com (Move, Inc.), playing a pivotal role in scaling one of the internet's most recognized consumer platforms. His leadership spanned product, technology, and go-to-market execution, combining consumer internet scale with SaaS operating discipline. Under his guidance, Realtor.com advanced its data-driven monetization strategy and solidified its position as a top digital property marketplace.
Enterprise IT Leadership Foundation
Bailey's executive career began at QAD Inc., a global ERP software company, where he served as Chief Information Officer. In that role, he led enterprise IT strategy, systems modernization, and infrastructure transformation. The experience gave him first-hand perspective on the challenges CIOs face balancing delivery, governance, and cost—a foundation that has strengthened his credibility with client executives throughout his consulting and solutions leadership career.
Across every role, Bailey has been at the forefront of emerging technologies. He has led enterprise programs in Generative AI and custom LLMs, designing architectures, governance frameworks, and adoption strategies. He has also driven advancements in SaaS innovation, quantum technologies, and digital transformation for complex global clients.
Leadership Philosophy & Future Vision
Bailey's career is defined by his ability to bridge technology economics, solutions engineering, and customer success to deliver tangible enterprise value. He thrives at the intersection of strategic vision, commercial growth, and deep technical leadership. He is now seeking full-time or contract senior executive roles—such as EVP, SVP, or VP of Solutions Engineering, Technology Economics, or Customer Success—at a growth-oriented technology or SaaS company, where he can scale teams, expand ecosystems, and deliver measurable business impact.
Connect with Bailey
Ready to discuss technology leadership opportunities or strategic consulting engagements?