Bobby Sincero

About Bobby Sincero

I am a Senior Technical Program Manager and Product Leader with over a decade of experience bridging the gap between state-of-the-art technology and mission-critical government requirements. My career has taken me from leading artillery operations in the U.S. Army to managing hyper-scale cloud data migrations at Microsoft and pioneering GenAI Test and Evaluation (T&E) at Scale AI. I specialize in \"De-Risking\" the impossible. Whether it is migrating 4PB of air-gapped data, standing up the first-ever LiDAR training queues for the public sector, or ghost-writing technical GTM strategy to close $50M+ federal contracts, I focus on the intersection of engineering execution and business value. Core Competencies:AI/ML Operations: LLM Test land Evaluation (T&E), RLHF, LiDAR Data Engine, Computer Vision Operations.Strategic Delivery: Technical GTM Enablement, Revenue Capture, Operational Risk Mitigation.

Experience

1. Senior Technical Program Manager

   Scale AI

   Nov 2023 — Present · Washington, DC, US

   Bridging the gap between Engineering, Product, and Operations to deliver cutting-edge AI/ML solutions for Federal and Defense clients. Focused on accelerating \"Time-to-Value\" for complex data engines and Generative AI deployments.Key Achievements:Revenue Growth: Orchestrated a critical 3-month extension of the Maven contract, generating $12M+ in invoiced revenue—the largest scale project by revenue and modality within the division.GenAI Leadership: Owned and executed the US Government’s first-ever Test & Evaluation (T&E) of Large Language Models for the CDAO, delivering executive briefings that directly resulted in a government-produced RFP.GTM Strategy: Partnered with Sales leadership to de-risk bottom-of-funnel deals, providing technical subject matter expertise that helped secure a 5-year,$50M IDIQ contract.Operational Risk: Managed the high-stakes \"sundown\" of the Yellowstone contract, successfully securing clearances and network access for dependent multi-million dollar programs (Horseshoe Bend, Redwood) during a critical cessation period.Innovation: Revitalized public sector LiDAR capabilities by pioneering the first use of commercial queues for workforce training in over 2.5 years.

Education

• United States Military Academy at West Point

  Bachelor of Science (B.S.), Art, Philosophy, and Literature w/ Computer Science concentration

  2010 — 2014