At Pickle Robot, we're on a mission to automate global supply chains with Physical AI. Our robots work alongside warehouse teams to unload trucks and containers — one of the toughest, most understaffed jobs in logistics — making the work safer, faster, and more efficient for the people doing it. Loading trucks comes next, followed by the Dill Autonomy Engine: generalized autonomy that will eventually orchestrate robots across entire logistics processes.
Pickle is looking for an experienced Senior Technical Program Manager (TPM) to join our Software Engineering organization and drive execution on the complex, cross-functional initiatives that power our autonomous robotics platform.
This role is ideal for someone with a strong technical foundation — ideally a former software engineer or someone with deep experience partnering with engineering teams. You'll work closely with software engineering, product management, robotics, firmware, and hardware teams to keep projects aligned, surface risks early, and hit critical milestones, delivering high-quality software that powers Pickle's robots in production warehouses.
What You'll Do
- Lead the planning, execution, and delivery of complex software engineering programs across Pickle's robotics platform, coordinating cross-functional initiatives involving Software, Robotics, Firmware, Product, Hardware, Manufacturing, and Deployment teams
- Partner closely with engineering leadership to establish priorities, define project plans, drive execution against key milestones, and improve predictability and overall software delivery
- Identify program risks, dependencies, and technical trade-offs, proactively drive resolution, and communicate status to stakeholders
- Facilitate planning activities including roadmap reviews, sprint planning, release planning, and program reviews
- Drive alignment across engineering teams while balancing changing priorities in a fast-paced startup environment
- Improve program execution and help establish best practices for technical program management — building scalable processes, tracking mechanisms, and communication frameworks as the engineering organization grows
What You'll Bring
Nice to have:
Pay at Pickle
Skills Required
- 5+ years of experience in Technical Program Management supporting software engineering organizations
- Strong technical background, ideally prior experience as a Software Engineer or highly technical engineering role
- Proven track record managing complex, multidisciplinary projects from conception to deployment
- Experience working closely with backend, infrastructure, robotics, embedded, or distributed systems engineering teams
- Strong understanding of Agile software development methodologies and modern software delivery practices
- Ability to understand technical architecture, identify dependencies, and facilitate technical tradeoff discussions
- Excellent communication and organizational skills with ability to influence across engineering disciplines
- Proven ability to manage multiple concurrent programs while maintaining exceptional attention to detail
- Willing and able to work from Charlestown office at least 3 days per week
- Comfortable operating in a fast-moving startup environment with evolving priorities and ambiguity
- Experience working in robotics, autonomous systems, industrial automation, or hardware-integrated software environments
- Experience supporting software organizations building distributed systems, robotics platforms, or AI-enabled products
- Familiarity with Jira, Linear, Asana, or similar engineering planning tools
- Experience coordinating software releases across multiple engineering teams
What We Do
We believe the best working experience is one where machines do the heavy lifting and people do the problem solving. Our robots work with people in the messy world of warehouse loading docks, reducing the real physical pain of unloading trucks and containers radically amplifying what each person can accomplish. Founded by an exceptional cast of robotics and machine learning experts, Pickle creates robots that work alongside people in the very messy world of the loading dock, reducing the backbreaking human effort that goes into getting your online orders to your door.
