Director of People Operations
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.
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.
What you'll do
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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.
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Build and implement agent-based automations to make day-to-day work more human.
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Design and scale People programs and processes that support Pickle's continued growth.
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Develop managers through coaching, leadership development, and performance management.
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Foster a high-performing, inclusive culture that reflects Pickle's values.
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Oversee compensation, benefits, HR operations, compliance, and People systems.
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Use people analytics to improve decision-making and organizational effectiveness.
What you'll bring
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10+ years of progressive People Operations or HR leadership experience, ideally within a high-growth company.
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Proven experience building and leading high-performing People and Talent teams, including employee relations—not simply operating as an individual HR contributor.
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Experience leading organizational change, restructures, and scaling organizations through periods of growth or transformation.
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Strong knowledge of multi-state employment law and HR compliance.
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Strong communication, coaching, and relationship-building skills.
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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.
Pay at Pickle
Benefits
As published by lever
Resume/CV, Full name, Pronouns, Email, Phone, Current location, Current company, LinkedIn URL, GitHub URL, Portfolio URL, Other website
- Are you willing and able to work from our Charlestown, MA worksites at least 3 times per week? written answer
- Would you, now or in the future, require immigration sponsorship for work authorization? choose one