Director of People Operations

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.

As Pickle enters its next phase of growth — scaling fast as a VC-backed company built by a team of MIT roboticists and engineers — we're hiring a Director of People Operations to help build the organization behind the technology. Reporting to the VP of Strategic Initiatives, you'll partner with executive leadership to shape Pickle's People strategy and build the systems, programs, and culture that let exceptional teams thrive, directly shaping how Pickle attracts, develops, and retains the talent it needs to scale.

We're looking for someone who has scaled a People function before, not just run one — someone equally comfortable setting strategy with executives and rolling up their sleeves to build the systems underneath it. If you thrive in fast-moving environments, we'd love to meet you.

• Lead Talent Acquisition and manage a team of recruiters and People Operations partners, owning workforce planning, organizational design, succession planning, and the end-to-end candidate experience as the company scales.

• Build and implement agent-based automations to make day-to-day work more human.

• Design and scale People programs and processes that support Pickle's continued growth.

• Develop managers through coaching, leadership development, and performance management.

• Foster a high-performing, inclusive culture that reflects Pickle's values.

• Oversee compensation, benefits, HR operations, compliance, and People systems.

• Use people analytics to improve decision-making and organizational effectiveness.

• 10 years of progressive People Operations or HR leadership experience, ideally within a high-growth company. 

• Proven experience building and leading high-performing People and Talent teams, including employee relations—not simply operating as an individual HR contributor. 

• Experience leading organizational change, restructures, and scaling organizations through periods of growth or transformation.

• Strong knowledge of multi-state employment law and HR compliance. 

• Strong communication, coaching, and relationship-building skills.

• Bonus points for experience supporting engineering or technical organizations, robotics, AI, automation, or other deep-tech environments, and familiarity with platforms such as Lever, Lattice, ADP, or Vestwell.