Trust & Safety Specialist

$90K - $100K/yr Pay Range
Full-time Job Type
On-site Work Arrangement
Mid-Level Experience
Apply Now Posted 1 hr ago

On-site in Chicago, Illinois, this mid-level role at Instawork focuses on maintaining the safety of their AI-powered labor marketplace. The Trust & Safety Specialist will handle complex safety incidents to protect the community.

Skills / Requirements

  • AI-driven Automation
  • Automated Workflow Design
  • Compliance
  • Data Analysis
  • Evidence-based Investigation
  • Fraud Detection
  • Low-code Automation
  • Natural Language to SQL
  • Operations
  • Policy Stewardship
  • Problem Solving
  • Safety Trend Analysis
  • SQL
  • Stakeholder Communication
  • Technical Communication
  • Trust & Safety
  • Vibe Coding

Why Apply

This role is ideal for someone skilled in vibe coding, using natural language to SQL for data interrogation. The position leverages AI-driven automation to streamline investigations and enhance operational efficiency.

What You'll Be Doing

You will lead investigations into safety incidents, ensuring evidence-based resolutions. This involves managing escalated support tickets, using data to identify trends, and designing automated workflows to improve processes.

Working in Chicago, Illinois

  • Chicago offers a robust tech job market with opportunities in various industries.
  • The city has a comprehensive public transit system, making commuting convenient.
  • Chicago is known for its diverse cultural scene, including music, art, and food.
  • The cost of living in Chicago is generally lower than in other major tech hubs like San Francisco or New York.

Pay and Career Growth

The role offers a competitive salary range of $90,000 - $100,000, with eligibility for stock options and comprehensive benefits. Instawork values high agency and ownership, providing a culture of learning and action-oriented decision-making.

Benefits and Perks

  • 401K plan
  • Commuter stipend
  • Dental plans
  • Employee discount program
  • Flexible paid time off
  • Flexible spending plans
  • HSA contribution
  • Medical plans
  • Paid Holidays
  • Phone stipend
  • Stock Options
  • Supplemental pay
  • Vision plans

Is This Role Right for You?

Good fit if you...

  • Experienced in Trust & Safety or compliance roles.
  • Comfortable using AI tools for data analysis and automation.
  • Thrives in environments requiring high ownership and decision-making.

May not be for you if...

  • Uncomfortable with AI-driven tools and automation.
  • Prefers rigid, manual processes over dynamic problem-solving.
  • Lacks experience in handling complex safety or compliance issues.

Original Job Description

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.

At Instawork, the safety of our marketplace is our highest priority. We are looking for a Trust & Safety Specialist who is, first and foremost, a meticulous and objective investigator. You will be responsible for protecting our community by resolving complex safety incidents with a firm commitment to evidence and policy.

To excel at the scale we operate, you must be highly proficient in modern operational leverage. This means using vibe coding (Natural Language to SQL) and AI-driven automation to gather facts, synthesize data, and streamline your workflow. We aren’t looking for someone to just follow a manual—we want an investigator who uses the latest technology to find the truth faster and more accurately.

Who You Are:

  • The Master Investigator: You have a “detective” mindset. You know how to weigh conflicting evidence, identify biases, and reach a fair conclusion under pressure.
  • AI-Native & Tech-Fluent: You are proficient in using AI to enhance your productivity. You understand how to use natural language to interface with data (vibe analytics) and automate repetitive administrative tasks.
  • High Agency: You take extreme ownership of your cases. You don’t just “process” a ticket; you solve the underlying problem.
  • Experience: 3+ years in Trust & Safety, Operations, or Compliance. Experience communicating with external stakeholders (clients, legal, or law enforcement) is a must.
  • Data-Inquisitive: You are comfortable navigating internal systems and using data to build a narrative of facts.

What You’ll Do:

  • Lead Complex Investigations: Your primary focus is the end-to-end resolution of safety incidents. You will conduct objective, unbiased, and thorough evidence-based investigations to protect all stakeholders on the platform.
  • Evidence-Based Resolution: Manage escalated support tickets with a cool head. You will communicate clearly and consistently with professionals and partners, ensuring that resolutions are grounded in facts and aligned with our terms.
  • Vibe Analytics (NL-to-SQL): Proactively interrogate our databases using natural language to generate SQL queries. You will pull your own data to identify fraud patterns and safety trends without needing a technical intermediary.
  • Policy Stewardship: Act as a subject matter expert on Instawork’s Community Guidelines. You will apply these policies with precision and help evolve them as the marketplace grows.
  • Automated Workflow Design: Identify manual bottlenecks in the investigation process and use AI or low-code automation to build scalable enforcement solutions.

For IL-based applicants:

  • The base salary for this position is $90,000 – $100,000
  • This position is eligible for equity in the form of stock options
  • This position is eligible for Instawork benefits, including:
    • A variety of medical, dental, and vision plans with coverage beginning on the date of hire
    • Flexible paid time off and paid company holidays
    • Phone stipend
    • Commuter stipend
    • Supplemental pay on qualified leaves
    • Employee health savings accounts (HSA) contribution
    • Flexible spending plans
    • 401K plan
    • Employee discount program

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 7 million 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 people who want to shape the future of work. With hubs in San Francisco, Bangalore, and Chicago, and offices in New York, Phoenix, and Singapore, we work together in person because we believe the best ideas happen face-to-face.

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

Personnel Privacy Policy
https://info.instawork.com/legal/california-personnel-privacy-policy