Senior IT Specialist

About this role:

Pickle is on the hunt for a dynamic and driven IT Support Lead to keep our rapidly growing robotics startup running smoothly. This role will focus on providing top-notch end-user support across Windows, Mac, and Ubuntu platforms while troubleshooting hardware and network issues. You'll be the go-to person for our team, ensuring they have the technical support they need to do their best work. As the first IT hire for Pickle, this position presents an exciting opportunity for an ambitious, process-oriented professional to take full ownership of the function and shape its future.

What You’ll Accomplish:

• Provide daily end-user support for Windows, Mac, and Ubuntu platforms, addressing a range of technical issues and escalating complex problems when necessary.
• Troubleshoot hardware and network-related issues for on-site users, ensuring minimal downtime and optimal performance.
• Own IT onboarding and offboarding for all employees.
• Partner with stakeholders in Engineering and external consultants to implement new IT security tools and best practices. 
• Offer excellent troubleshooting and communication support, helping users understand and resolve technical challenges.
• Assist with user support and basic administration for tools such as Okta, Kollide and 1Password, managing access and security efficiently.
• Support our engineering team by providing assistance with key tools, including Atlassian platforms, Slack, and G-Suite administration.
• Collaborate with highly technical end-users, understanding their unique needs and delivering tailored support.
• Document processes and common issues to improve efficiency and self-service resources.

Who You Are:

• 5+ years of experience in end-user IT support, preferably in a fast-paced startup or technology environment.
• Proven experience providing support for Windows, Mac, and Ubuntu operating systems.
• Strong troubleshooting skills in both hardware and networking, with the ability to resolve issues independently.
• Excellent communication skills, with the ability to explain technical concepts to non-technical users alike.
• Proven track record of implementing new tools and programs in IT.
• Familiarity with tools like Okta, 1Password, Atlassian platforms, Slack, and G-Suite is a plus.
• Comfortable working with highly technical end-users, adapting to their needs and problem-solving efficiently.
• A proactive, solutions-oriented mindset with a strong focus on customer service.
• Willing and able to work from our offices in Cambridge and Charlestown at least four days per week.

About Pickle Robot

Pickle Robot is a pioneer in Physical AI for supply chain applications. Today Pickle robots autonomously unload trucks, trailers, and import containers at human-scale or better performance. The alternative is manual work that is difficult, dirty, sometimes dangerous, and increasingly hard to staff at distribution centers around the globe. Pickle Robot is laser focused on automating truck unloading using generative AI, machine learning, computer vision, advanced sensors, and industrial robotics to deliver engineered products customers rely on. Pickle Robot Unload Systems work alongside people on loading docks to make the work safer, faster, and more efficient. Pickle robots are physical AI that unload trucks.

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.