Empowering growth-minded SaaS and technology leaders to scale profitably through AI-powered innovation and disciplined FinOps.
Bailey H. Caldwell Consulting
About Bailey
Executive Level Technical Leader with 30+ years across software and technology industries. Former Associate Partner at McKinsey & Company and founding member of Cloud by McKinsey; built, led and scaled the technology economics and FinOps practice.
My passion lies in helping technology companies navigate complex transformations—whether that's optimizing cloud economics, deploying enterprise AI solutions, or scaling customer success operations. Having worked with Fortune 500 enterprises and high-growth startups alike, I bring both strategic vision and hands-on execution experience.
Expertise spans GenAI & Custom LLM deployments, Cloud & FinOps excellence, SaaS business transformation, Sales Engineering acceleration, and Customer Success optimization. Previous leadership roles at McKinsey & Company, Flexera, RightScale, Paxonix Inc., and Realtor.com consistently driving innovation and operational excellence.
Commercial Acceleration Across the Customer Lifecycle
GenAI & Custom LLM Deployments
Build and fine-tune AI models that align with your enterprise workflows, with governance baked in.
Strategic advisory for AI integration, custom LLM development & fine-tuning, AI architecture & deployment, responsible AI & governance, and AI-driven business process optimization.
Cloud Cost Optimization & FinOps Excellence
Automate visibility into cloud spend and implement best-practice governance to maximize ROI.
Implement and scale FinOps practices to effectively measure and optimize cloud spend, utilizing cloud-native tools and automation solutions. Procurement and negotiation strategies for cloud contracts.
SaaS Product & Business Transformation
Navigate the complete journey from on-premise to scalable cloud-native SaaS solutions.
Strategic guidance for companies transitioning from on-premise to cloud/SaaS models, including pricing strategy, migration planning, architecture optimization, and scaling operations.
Sales Engineering & Customer Success
Accelerate the 'technical yes' and build retention programs that drive sustainable growth.
Design and enhance customer success organizations, develop proactive retention programs, and establish 24x7 global support operations. Scale Sales Engineering teams to accelerate customer win rates during the buying process.
Strategic Partnerships & Commercial Growth
Build ecosystem partnerships that create new revenue streams and accelerate market penetration.
Formulate global business development strategies, cultivate strategic alliances across ISV, Channel and Technology ecosystems. Implement partnership models with measurable success rates.
Leadership Development & Operational Excellence
Foster cultures of innovation while building scalable systems and high-performing teams.
Guide organizations in developing leadership capabilities, implementing accountability frameworks, and building scalable systems across critical business processes.
Ready to Accelerate Your Growth?
Let's discuss how we can optimize your technology business for sustainable, profitable growth.