Dylan Kenney
Director of Engineering | Scaled orgs 0→50+ | AI Systems, Cloud Platforms, High-Performance Teams
- Role
- Director of Engineering at Vividcloud
- Location
- Portland, ME, US
- LinkedIn followers
- 500 followers
About Dylan Kenney
Director of Engineering & AI Solutions Leader with 10+ years scaling high-performing engineering orgs, building AI-native systems, and delivering enterprise platforms used by Fortune 100 clients. Former CTO who grew multi-disciplinary teams from 0→50+ across software, hardware, and operations.I specialize in org design, engineering excellence, and transforming ambiguous problems into scalable, AI-driven solutions. At VividCloud, I lead AI initiatives, built a reusable RAG/agentic framework, launched Code Labs (65% org engagement), and drove a major robotics-emulation platform for Walmart that cut iteration costs and timelines dramatically.I’m passionate about building elite engineering cultures that ship high-quality software, improve velocity, and tie engineering outcomes directly to business results.
Experience
Director of Engineering
Sep 2019 — Present · Brunswick, ME, US
Lead the engineering organization across multiple disciplines - defining technical direction, scaling teams, and driving innovation in AI and cloud-based systems. Focused on delivery excellence, team development, and building strong client partnerships.Engineering Leadership & Team Development• Built and scaled high-performing engineering teams with onboarding, learning, and growth programs that fostered retention and professional development.• Launched the internal “Code Labs” initiative, achieving 65% company-wide engineer participation through bi-weekly sessions that strengthened engagement and knowledge sharing.• Mentored engineers across all levels, establishing clear career paths and individualized growth plans.Business Impact & Client Delivery• Managed project profitability, resourcing, and timelines across multiple concurrent client engagements.• Supported sales and presales efforts, including solution architecture design, technical proposals, client presentations, and resource planning.Technical Innovation & Architecture• Architected a robotic hardware emulation system, enabling virtualized testing and significantly reducing development costs and iteration time.• Led company-wide AI and RAG (Retrieval-Augmented Generation) initiatives, building a reusable agentic framework with specialized, customizable agents.• Drove evaluation and adoption of emerging AI tools and developer productivity technologies to enhance delivery velocity and team efficiency.
Education
University of Southern Maine
Bachelor of Science - BS
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