Director of People Operations

Posted One Month Ago
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Charlestown, MA, USA
Hybrid
194K-216K Annually
Expert/Leader
Robotics • Transportation
The Role
Lead Talent Acquisition and People Operations, manage recruiters and People partners, own workforce planning, org design, succession planning, and candidate experience. Build automations, scale people programs and systems, develop managers, oversee compensation, benefits, HR operations, compliance, and People systems, and use people analytics to improve organizational effectiveness and decision-making.
Summary Generated by Built In
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

  • 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.

What You'll Bring

  • 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. 

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. 

Skills Required

  • 10+ years of progressive People Operations or HR leadership experience
  • Proven experience building and leading high-performing People and Talent teams, including employee relations
  • Experience leading organizational change, restructures, and scaling organizations
  • Strong knowledge of multi-state employment law and HR compliance
  • Strong communication, coaching, and relationship-building skills
  • Experience supporting engineering or technical organizations, robotics, AI, automation, or other deep-tech environments
  • Familiarity with platforms such as Lever, Lattice, ADP, or Vestwell
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The Company
HQ: Cambridge, MA
40 Employees
Year Founded: 2018

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.

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