Executive Assistant

Pickle is seeking a highly capable Executive Assistant to support senior executives with a primary focus on investor engagement and executive operations. This role sits at the center of high-stakes external collaboration, requiring exceptional organization, discretion, and communication. You will directly support these efforts by coordinating executive and investor meetings, preparing materials and spaces, managing outreach workflows, and maintaining accurate contact and meeting records.

• Coordinate and schedule high-volume investor, board, and executive meetings across multiple time zones
• Manage executive calendars, resolving conflicts and handling frequent last-minute changes
• Prepare meeting rooms and virtual setups, including agendas, materials, and attendee readiness
• Organize and maintain investor, advisor, and partner contact lists
• Support outbound investor outreach by organizing contact data, drafting and proofreading communications, and tracking responses
• Draft, edit, and proofread polished written communications on behalf of executives
• Track meeting outcomes, follow-ups, action items, and next steps
• Maintain accurate records and activity tracking in CRM or similar systems
• Support fundraising and executive operations through ad hoc projects and administrative tasks
• Improve organization of executive workflows, templates, and documentation
• Anticipate executive needs and proactively address issues before they escalate

• 3+ years of experience in executive support, operations, or administrative roles supporting senior leaders
• Experience supporting externally facing initiatives, strategic programs, or commercial operations preferred
• Demonstrated track record of excellence in fast-paced environments
• Exceptional written communication skills with the ability to produce clear, professional, and well-structured content
• Strong verbal communication skills and comfort interacting with executives and external stakeholders
• Polished, professional demeanor in executive and external-facing settings
• High attention to detail and sound judgment regarding confidentiality and discretion
• Working familiarity with CRM systems such as Salesforce, HubSpot, Affinity, or similar software tools strongly preferred
• Strong proficiency with spreadsheets and standard office productivity tools, including word processing and document collaboration software
• Comfortable learning new tools and adapting to evolving processes
• Highly organized, reliable, and proactive with strong follow-through
• Ability to manage ambiguity and prioritize competing demands
• Interested in and able to grow the role and taking on expanded responsibilities over time
• Able to work on site at Pickle’s Charlestown, MA office at 4+ days per week

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.