Pickle is looking for an experienced Senior Technical Program Manager (TPM) to join our Software Engineering organization and help drive the execution of 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—who enjoys bringing clarity, organization, and momentum to fast-moving technical programs.
You'll work closely with software engineering, product management, robotics, firmware, and hardware teams to ensure projects stay aligned, risks are identified early, and critical milestones are achieved. You'll help coordinate software initiatives across multiple engineering disciplines, enabling the team to deliver high-quality software that powers Pickle's robots in production warehouses.
We're looking for someone who can ramp quickly, take meaningful ownership from day one, and thrive in a collaborative startup environment where priorities evolve rapidly.
Responsibilities
Lead the planning, execution, and delivery of complex software engineering programs across Pickle's robotics platform.
Partner closely with software engineering leaders to establish priorities, define project plans, and drive execution against key milestones.
Coordinate cross-functional initiatives involving Software, Robotics, Firmware, Product, Hardware, Manufacturing, and Deployment teams.
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.
Improve program execution by developing scalable processes, tracking mechanisms, and communication frameworks.
Drive alignment across engineering teams while balancing changing priorities in a fast-paced startup environment.
Partner with engineering leadership to improve predictability, execution, and overall software delivery.
Help establish best practices for technical program management as the engineering organization continues to grow.
Skills & Experience:
- 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 of successfully 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 discussions around technical tradeoffs.
Excellent communication and organizational skills with the ability to influence across multiple engineering disciplines.
Proven ability to manage multiple concurrent programs while maintaining 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 HaveExperience working in robotics, autonomous systems, industrial automation, or another hardware-integrated software environment.
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.
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.
