Director of Technical Project Management

About this role:

Pickle is on the hunt for a dynamic and driven Director of Technical Project Management to revolutionize the future of warehouse automation. In this role, you will be responsible for overseeing complex robotics and AI-driven hardware/software deployments, ensuring projects are delivered on time, within scope, and with uncompromising quality. You'll drive cross-functional collaboration, working with engineering, product, deployment, and operations teams to scale Pickle’s systems across customer sites.

• Deliver major customer deployments on time, within scope, and at a high level of quality.
• Coordinate engineering, deployment, and operations workstreams to ensure alignment and mitigate risk.
• Stand up lightweight but effective processes for tracking cross-functional execution at all phases of the customer lifecycle.
• Recruit, lead, and coach a team of program and project managers.
• Ensure compliance with industry regulations, safety standards, and best practices in robotics development.
• Maintain clear, regular communication with leadership on project health, timelines, and risks.
• Translate ambiguous or conflicting needs into actionable plans and drive resolution across technical and business stakeholders.
• Identify operational gaps and implement scalable systems and tools to close them.
• Identify and implement process improvements to enhance program execution efficiency and scalability.
• Partner with supply chain, manufacturing, and deployment teams to ensure seamless integration and production of robotics solutions
• Own and administer the Engineering Change Management (ECM) process, ensuring smooth BOM management and drawing release workflows.

• A seasoned project or program leader with 8+ years of experience delivering complex hardware/software programs.
• A people manager with at least 4 years of experience leading project management teams.
• Experienced in scaling and shipping robotics, automation, or physical systems into real-world environments.
• Comfortable managing ambiguity and driving clarity in fast-paced, cross-functional settings.
• Experienced with Engineering Change Management (ECM), BOM management, and drawing release processes; familiarity with Arena is a plus.
• Deeply familiar with Waterfall, Phase-Gated, Agile, and Scrum project management methodologies; experience with Jira and Smartsheet is a plus.
• Skilled at identifying technical trade-offs, prioritizing critical tasks, and solving complex challenges in robotics development.
• An excellent communicator who brings structure, urgency, and confidence to both executive and frontline conversations.
• A natural operator who builds trust across teams by doing what you say you’ll do.
• Process-minded but not process-bound—able to simplify ruthlessly in the name of execution.
• Familiar with project tools and methodologies (e.g., Jira, Confluence, Smartsheet, Gantt, RACI) but not reliant on any one system.
• Willing and able to work from our headquarters in Charlestown, MA, at least three times per week.

About Pickle Robot

Pickle Robot is a pioneer in Physical AI for supply chain applications. Today Pickle robots autonomously unload trucks, trailers, and import containers at human-scale or better performance. The alternative is manual work that is difficult, dirty, sometimes dangerous, and increasingly hard to staff at distribution centers around the globe. Pickle Robot is laser focused on automating truck unloading using generative AI, machine learning, computer vision, advanced sensors, and industrial robotics to deliver engineered products customers rely on. Pickle Robot Unload Systems work alongside people on loading docks to make the work safer, faster, and more efficient. Pickle robots are physical AI that unload trucks.

Pickle provides best-in-class benefits including health, dental, & vision insurance; unlimited vacation, along with all federal and state holidays; 401K contributions of 5% your salary, travel supplies, and other items to make your working life more fun, comfortable, and productive.