Senior Technical Program Manager - Robotics

About this role 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 Have Experience 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. 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. About Pickle Robot Want to get in on the ground floor of a fast-growing, VC-backed robotics company? Join Pickle Robot! We build systems that companies and their teams love. Pickle robots unload trucks. Every day, millions of trucks and containers are loaded and unloaded, often requiring manual labor—tough, dirty, dangerous, and hard to staff. Pickle automates this process using AI, machine learning, and robotics to deliver reliable products. Our Unload Systems work with teams on loading docks to make the job safer, faster, and more efficient. 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.