Paralegal (Contractor)

Instawork is on a mission to create meaningful economic opportunities for skilled hourly professionals in communities around the globe. Our AI-powered labor marketplace helps local businesses scale, and enables global technology companies to push the frontiers of robotics and AI. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we’re looking for exceptional talent to reimagine the way the world works. We're looking for a Paralegal (Contractor) to join our in-house Legal Compliance team. This is a contract engagement of up to 6 months at approximately 30–40 hours per week, available to start immediately. The Contractor will apply legal, compliance, and technical skills, and will exercise independent judgment in determining how to accomplish the work described below. The right Contractor will have the opportunity to be selected for our open full-time Paralegal role, which is based in San Francisco, CA. This role sits at the intersection of Legal, Finance, and Compliance. You'll own regulatory registrations, data requests, and case management, and you'll build and improve the workflows that support those functions. We don't just want someone who can do the work; we want someone who learns a skill and then asks, "how do I automate this shit so it runs itself?" If you've built an N8N workflow, trained a custom GPT, scripted a process in Google Apps Script, or prototyped with no-code tools, and you want to bring that mindset to a legal team, this is the role. The ideal candidate takes their work seriously but not themselves. You're organized, systems-minded, and energized by a fast-moving environment where priorities shift and no two days look the same. You take ownership of your work, bring sound judgment, and are always looking for a better way to get things done. Location: Remote (U.S.-based). Must be available, as needed, to share deliverables and discuss projects during Pacific Time business hours. The full-time role, if offered, is based in San Francisco, CA (in-office). Engagement: Contract, approximately 30–40 hours/week, up to 6 months. Potential conversion to full-time employment. Start Date: Immediately Who You Are: Bachelor's degree and 3+ years of experience in a legal, compliance, operations, and/or project management role (Paralegal certificate preferred, but not required) Strong verbal and written communication skills Exceptionally organized, efficient, and detail-oriented Drive to use AI tools and legal technology to improve efficiency, with a willingness to identify and adopt new approaches Ability to work independently with minimal direction, applying specialized legal and compliance expertise to deliver complete work product Ability to manage multiple priorities simultaneously, exercise sound judgment, and meet deadlines with minimal supervision Proficiency working with MacOS and iOS, Google Apps, DropBox, Slack, Microsoft Office Collaborative and team-oriented, with the ability to build relationships across departments A continuous improvement mindset: you value what works today and are always looking for what could work better tomorrow Preferred Qualifications: Prior in-house legal department experience Experience with legal technology platforms, e-discovery tools, or contract management systems Licensed Notary Public, or willingness to obtain Enthusiasm for Instawork's mission of creating economic opportunity What You'll Do: Core Legal Compliance File, track, and maintain corporate and commercial registrations; federal, state and municipal licenses; and records Receive, track, and coordinate notices for all legal, administrative, and tax matters, including work verification, unemployment, disability, and wage garnishments Research emerging federal, state, and municipal regulations that may apply to Instawork and its subsidiaries, independently assess their applicability, recommend a compliance approach, and operation ... (truncated, view full listing at source)