About Us
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
5+ years of experience in Technical Program Management or Technical Project Management supporting software engineering organizations
Strong technical background, ideally with prior experience as a Software Engineer or in another highly technical engineering role
Proven track record managing complex, multidisciplinary projects from conception to deployment, including coordinating software releases across multiple engineering teams
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 discussions around technical tradeoffs
Excellent communication and organizational skills, with the ability to influence across multiple engineering disciplines and manage multiple concurrent programs with exceptional attention to detail
Comfortable operating in a fast-moving startup environment with evolving priorities and ambiguity
Willing and able to work from our Charlestown office at least 3 days per week
Nice to have:
Familiarity with Jira, Linear, Asana, or similar engineering planning tools
