Jacob Shea

Built a portfolio of 120+ companies achieving 6 public company outcomes by raising and deploying three VC funds totaling $100M+ AUM with 7 SPVs across all verticals and industries. Fund Sample: Carta, Forge, Uber, Artera, Porch, Classpass, Vessel, OhmConnect, Peerspace, Honk, RO, Cargomatic, SHIFT, etc.

Accelerated portfolio company growth faster than industry average by stepping in as seasoned CTO/VP of Technology in formal and informal roles, providing hands-on technology guidance and strategic execution support. Grew VC network and ecosystem relationships, responsible for LP communication and all technical & data aspects of portfolio companies. 

Improved portfolio company success rate by delivering ongoing support for technical strategy and growth. Consumer, Healthcare, B2B and Marketplaces.

Architected OBI’s AI systems from the ground up, defining the AI strategy, building multi-model infrastructure, and shipping production features that reduce user workload and increase automation. Designed orchestration layer routing tasks across OpenAI GPT, Anthropic Claude, Groq’s framework, and Apple’s on‑device Foundation Models optimizing for latency, accuracy, and cost. Built in NUXT 4, Supabase, Swift 6, Edge Functions, etc

Built OBI’s context-aware intelligence framework that merges property data, user preferences, weather, and maintenance history, enabling “Ask OBI” to deliver personalized, actionable guidance. Examples include anticipating routines for properties, savings for home, recommendations before storms or tailoring tasks to installed smart property systems.  Implemented governance across model evaluation, fallback logic, routing strategy, and real-time streaming.

Increased platform reliability and reduced operating costs by leading complete migration from Parse platform to custom software stack during Y Combinator program. Scaled 300% daily active users by developing mobile apps for on-demand food rescue services while maintaining 95% uptime. Reduced technical debt by parachuting in as VC-turned-CTO to stabilize technology infrastructure during critical growth phase.