Chris Dolezalek
Executive Vice President, R & d @Hum Capital
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WORK HISTORY
Executive Vice President, R & d @Hum Capital
US
Lead end-to-end R&D and engineering delivery for an AI/ML-driven FinTech marketplace, owning architecture, platform reliability, infrastructure engineering, DevOps, CI/CD, and developer productivity across the organization.• Modernizing engineering workflows by rebuilding CI/CD pipelines, strengthening SRE practices, improving observability, and streamlining infrastructure operations—reducing friction across data, ML, and application teams.• Direct platform-level modernization, clarifying system boundaries, improving scalability, and guiding architectural evolution as the company integrated LLMs and deeper AI-driven analytics.• Served as interim CPO, aligning product strategy with engineering reality and establishing cross-functional OKRs that connected roadmap priorities to delivery capacity and system constraints.• Provide operator-rooted coaching and advisory support for engineering leaders—focusing on organizational clarity, technical debt strategy, and leadership development during periods of rapid change.• Maintain hands-on technical depth through code and architecture reviews and by personally applying AI-assisted development patterns to internal tools and workflows.• Provide occasional coaching and advisory support to senior engineering leaders and executives.
EDUCATION
University of Virginia
BS, Physics
SKILLS
ABOUT CHRIS DOLEZALEK
Chris Dolezalek (CD) is an engineering executive and executive coach who has helped build and scale 11 companies—three IPOs, three acquisitions, and seven unicorns—with cumulative valuations exceeding $400B. He has led product and engineering organizations through hyper-growth, existential crises, and complex technical turnarounds. Across these roles, CD has owned DevOps, CI/CD, SRE, platform reliability, developer tooling, and infrastructure engineering—including 7–9s uptime at scale.CD’s technical foundation includes building two operating systems, architecting the industry’s first integrated IDE, guiding category-defining platforms from BroadVision’s $25B rise to QuickBooks Online’s early architecture, and leading modern AI/ML systems at Prosper and Hum Capital. He maintains hands-on depth through weekly code and architecture reviews—linking strategy to implementation in a way few engineering leaders do.CD also keeps an active maker’s mindset. He is currently building a native Android Senior Companion app in Kotlin using AI-assisted development and an AI-powered financial analysis tool that reveals sector and vector insights often missed in traditional aggregate evaluations. These projects keep him grounded in the practical realities of modern engineering and the rapid pace of AI-driven reinvention.He stepped away from tech to teach K–8 students in diverse communities, then returned as an IC at Intuit before rising to Director—an experience that deepened his belief that “what got you here won’t get you there.” His work reflects the conviction that growth depends less on what you know than how you learn and adapt.Alongside his operating roles, CD advises founders, CTOs, and engineering leaders navigating complexity, organizational design, technical debt, and the transition from doing to enabling. He has coached dozens of leaders on their path to VP or C-level roles, helping teams build clarity, capability, and resilience in moments that matter.Having survived two near-death experiences, CD understands how crisis clarifies purpose—for people and for companies. As Andy Grove wrote:“Bad companies are destroyed by crises. Good companies survive them. Great companies are improved by them.”
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