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Hello! đź‘‹

I'm Jon Kaplan

Product & Technical Leader | Autonomous Systems, Robotics, & AI

About Me

My passion is being the technical translator between complex user needs and engineering teams. I thrive in high-stakes, regulated environments—like autonomous aviation and defense—where the margin for error is zero. My product philosophy is built on: 1. System-Level Thinking: I don't just manage features. I lead product for complex, interconnected systems of hardware, software, and human operations. 2. Enabling AI with Humans: My expertise is in the 'human-in-the-loop' systems that make AI safe, efficient, and scalable in the real world. 3. First-Principles Problem Solving: From my engineering roots, I dig deep into the 'why' to find the root cause, whether it's in a data pipeline, an operational bottleneck, or a user workflow.

Product Strategy & Leadership

AI/ML Product Roadmapping Autonomous Systems Product Mgmt Cross-Functional Team Leadership PM Mentorship & Development

Technical & AI Enablement

AI-Driven Decision Systems Human-in-the-Loop (HITL) Interfaces Predictive AI Modeling Python, SQL, MATLAB

Platform & GTM

External & Partner-Facing APIs Developer Platform Creation Data Governance & Security Data Pipeline & Quality Management

Regulatory & Compliance

Aviation Regulatory Compliance (FAA, EASA, CASA) Defense (DoD) & SBIR Contracts Safety-Critical Systems

Experience

Product Manager II (L5)

Wing (An Alphabet Company)

November 2022 - Present
  • Own and execute the product vision for Wing's next-generation ground software platform, enabling thousands of daily autonomous flights.
  • Engineered and executed a multi-year, globally compliant teleoperations roadmap that resulted in a 50% reduction in operator costs per delivery, a key enabler for scaling the business.
  • Lead a cross-functional team of 10+ engineers, 3 PMs (including mentoring rotational/contract PMs), and UX designers through rapid, safety-critical launch cycles.
  • Scaled the operations platform to 30+ sites, supporting Fortune 500 partners like Walmart and DoorDash, with a clear roadmap for 100+ sites in 2026.
  • Owned the product strategy for regulatory compliance, successfully securing approvals from global aviation regulators (FAA, EASA, CASA) for autonomous operations.

Product Manager

Dephy, Inc.

May 2021 – November 2022
  • Drove annual revenue by building and managing a B2B developer platform with well-documented APIs that enabled 20+ research institutions to build on standardized robotics hardware.
  • Achieved product-market fit with over 20+ active customers by creating technical documentation and developer support for researcher-led AI controller development.
  • Secured SBIR funding for exoskeleton development spanning Army and Air Force use cases through successful DoD stakeholder engagement.

Software Engineer

Dephy, Inc.

March 2020 – April 2021
  • Developed an embedded AI model that achieved 99% accuracy in real-time human running gait detection for a bilateral exoskeleton.
  • Awarded two U.S. patents for innovating real-time feedback control and ML-driven exoskeleton optimization.
  • Reduced developer data processing time by 90% by creating standardized data analysis tools in Python/MATLAB.

Research Engineer

U.S. Army - Natick Soldier Systems Center

June 2015 – February 2020
  • Led development of predictive AI models for CT scan automation, successfully forecasting knee injury likelihood with high accuracy in a defense-relevant application.
  • Secured over $400K in research grants, directing a multi-year computational biomechanics research roadmap.

Education

M.S., Biomedical Engineering

University of Connecticut

    B.S., Biomedical Engineering

    University of Connecticut