Operations Support Specialist Jobs in Massachusetts

About this role:

Pickle Robot is looking for a Robotic Operations Support Specialist to join our fast-growing team on a night/shoulder shift. You'll serve as frontline support for our robotic unload systems deployed in logistics warehouses across the U.S., ensuring they run smoothly during evening operations and customers are supported with confidence.

This is a night/shoulder shift position based in Boston, MA, with hours likely 2 PM–10 PM or 4 PM–12 AM.

This role sits at the intersection of engineering, product, and customer operations. You'll work with cross-functional teams—including Hardware & Software Engineering, Product Management, and Go-to-Market—to identify, resolve, and prevent field issues while feeding real-world insight back into the product development cycle.

You'll be known to our customers as a trusted partner during critical operational hours and to our engineering team as "ground truth" from the field. If you're a fast learner, an independent thinker, and thrive in dynamic environments, this is your chance to make a significant impact.

Responsibilities:

• Initial Field Training: 2 weeks in HQ, 2 weeks in the field: Participate in on-site deployment operations and system commissioning to gain a deep understanding of our robotic truck unload platform, as well as our customer stakeholder landscape.
• Remote Monitoring & Support (Night/Shoulder Shift): Track fleet performance using telemetry and logging dashboards during evening and overnight hours when warehouse operations are most active.
• Identify and flag potential issues before they escalate during peak customer operational periods.
• Real-Time Troubleshooting: Diagnose and resolve issues across software, electrical, and mechanical components.
• Provide live support for customer stakeholders and internal teams during night/shoulder shift hours.
• Cross-Team Communication: Manage support cases via phone, video, and written updates.
• Log findings, resolution steps, and maintain clear follow-up loops with day shift teams.
• Technical Investigations: Triage issues that span across disciplines and escalate effectively.
• Guide field teams through on-site troubleshooting and retrofits.
• Process Refinement: Identify and help close gaps in tooling, workflows, and documentation.
• Hardware Maintenance: Perform scheduled and ad hoc maintenance on robotic arms, conveyors, and electrical components.

Skills:

• 1–3 years working with robotic, automated systems, or industrial equipment in production or logistics environments.
• Comfortable working night/shoulder shifts (2 PM–10 PM or 4 PM–12 AM schedule).
• Experience in a customer-facing or technical support role is a plus.
• Software: Familiar with CLI tools (e.g., ssh), interpreting logs, and system telemetry.
• Electrical: Basic knowledge of industrial robotics, PLCs, sensors, wiring, and protocols.
• Mechanical: Experience with electromechanical subsystems and field repair workflows.
• Strong communicator across both technical and non-technical stakeholders.
• Capable of building trust with both customers and engineering teams.
• Self-directed and comfortable working independently during non-standard hours.

Preferred Skills:

• Fluent in Spanish.
• Familiarity with tools like Jira, Freshdesk, or related systems.
• Interest in process improvement and documentation.
• Calm under pressure; curious and proactive.
• Adaptable in fast-paced environments.
• Customer-first mindset.
• Experience working night shifts or non-traditional hours.
• Physically capable of lifting and moving up to 50 lbs.
• Willingness to work in hot/cold and uncomfortable conditions (warehouses are often not climate-controlled).
• Valid driver's license and clean driving record.

Location & Travel:

• Based in Boston, MA (Cambridge or Charlestown preferred).
• Night/shoulder shift hours: likely 2 PM–10 PM or 4 PM–12 AM.
• Willing and able to travel 10–20% of the time to customer locations across the U.S.

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.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.