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Paralegal (Contractor)

Remote, United States

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 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

Compensation (CA-based applicants):

  • 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.

#LI-Remote

Our Values 

  • Empathy, Trust & Candor
    We put ourselves in the shoes of our colleagues and customers and don’t shy away from uncomfortable conversations, instead building trust through honest and direct feedback.

  • Bias for Action
    We practice high-velocity decision-making, clear-eyed that we often operate with incomplete information. Growing quickly means it’s OK to be wrong, so long as we learn from our mistakes and course correct!

  • Always Be Learning
    We’re a curious bunch, and with AI transforming our workplace we encourage everyone to learn from each other, compounding our knowledge and experience to help us change an entire industry.

  • Act Like an Owner
    We work long, hard, and smart, building products that delight our users and drive growth. Your ability to impact Instawork is limited only by your courage and conviction, not your job description.

About Instawork

Founded in 2015, Instawork is the nation’s leading online labor marketplace for food services, hospitality, light industry, and logistics, connecting more than 7M skilled workers with local restaurants, hotels, warehouses, stadiums, and more. Our AI-powered platform serves thousands of businesses across more than 50 major markets in the United States and Canada. We're not just helping fill shifts, we're supporting local economies—and we're just getting started!

Instawork has been featured by CBS News, The Wall Street Journal, The Washington Post, and the Associated Press. Forbes included us on their Next Billion Dollar Startups list; RetailTech Breakthrough named us Workforce Hiring Solution of the Year for 2025; and Inc. 5000 recognized us as one of the country's top 10% fastest-growing companies two years in a row. But what matters most is our impact. We're solving real problems for real people, and we’re doing it at scale.

Join our team to help us build something that matters! We’re looking for superstars who want to help us shape the future of work. With hubs in San Francisco, Bangalore, and Chicago, city offices in New York, Phoenix, and Singapore, we're back to working together in-person five days a week because we believe the best ideas happen when great people collaborate face-to-face. We also value diverse perspectives and encourage applications from candidates of all backgrounds.

Ready to make an impact? Learn more at www.instawork.com/about.

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