Job Specifications
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.
Responsibilities:
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
Skills & Experience:
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.
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.
About the Company
We believe the best working experience is one where machines do the heavy lifting and people do the problem solving. Founded by an exceptional cast of robotics and machine learning experts, Pickle Robot is a pioneer in Physical AI for supply chain applications. Today our robots autonomously unload trucks, trailers, and import containers at human-scale or better performance. We are laser focused on automating truck unloading using generative AI, machine learning, computer vision, advanced sensors, and industrial robotics to d...
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