Paralegal (Contractor)

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: Ideally SF, but open to 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

• 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

• 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

• 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 operationalize ongoing maintenance of any resulting obligations
  • Prepare for, assist, and/or attend administrative hearings
  • Support counsel by independently tracking and managing calendaring for demands, deadlines, and hearing dates
  • Coordinate cross-departmental requests (e.g., Legal, Finance, HR)
  • Work closely with counsel to research and respond to law enforcement and third-party data requests, applying judgment to prioritize and triage incoming requests
  • Assist in-house counsel with handling of pre-litigation and litigation matters, as well as external legal requests
  • Manage administrative tasks related to contract lifecycle management and certificates of insurance; assist with annual insurance renewals
  • Develop and provide reporting and metrics on litigation, compliance, and other legal matters, using independent judgment to identify meaningful trends and flag items requiring attorney attention
  • Support special projects as directed by counsel, with the flexibility to adapt as priorities evolve

• AI, Automation & Process Improvement
  • Evaluate every recurring legal and compliance workflow for automation potential, then independently build or propose solutions
  • Design and maintain automations for tasks like deadline tracking, registration renewals, notice routing, reporting, and document intake using tools like Cursor and Replit
  • Use AI tools (e.g., ChatGPT, Claude, Gemini, GC.ai) to accelerate research, drafting, document review, and data extraction, and develop reusable prompts or workflows the team can adopt
  • Track and evaluate new legal technology, AI products, and automation platforms, and recommend tools that would benefit the team
  • Design and document processes and playbooks so that institutional knowledge lives in systems, not in people's heads

• Hourly rate: $45–$55/hour, commensurate with experience
• This is a contract (1099) engagement. Benefits are not included, but the role carries the potential for conversion to a full-time position with full benefits and equity.

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