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 trade-offs

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 Pay at Pickle At Pickle Robot Company, we believe transparency builds trust. The salary range listed here is provided in accordance with Massachusetts law and reflects what we reasonably and in good faith expect to offer for this role. We often consider candidates at different levels of seniority, and final compensation will reflect the level at which a candidate is hired, along with factors like experience and location.   Pickle Perks  Pickle provides best-in-class benefits, including health, dental, and vision insurance; unlimited vacation; paid federal and state holidays; 401(k) contributions of 5% of your salary; company-covered travel expenses; and other perks to make your working life more fun, comfortable, and productive.

Pay at Pickle

At Pickle Robot Company, we believe transparency builds trust. The salary range listed here is provided in accordance with Massachusetts law and reflects what we reasonably and in good faith expect to offer for this role. We often consider candidates at different levels of seniority, and final compensation will reflect the level at which a candidate is hired, along with factors like experience and location.

Pickle Perks 

Pickle provides best-in-class benefits, including health, dental, and vision insurance; unlimited vacation; paid federal and state holidays; 401(k) contributions of 5% of your salary; company-covered travel expenses; and other perks to make your working life more fun, comfortable, and productive.