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Content, QA, And Learning Development

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Polymarket
Full Time position
Listed on 2026-10-03
Job specializations:
  • Business
    Regulatory Compliance Specialist
Salary/Wage Range or Industry Benchmark: 200000 - 250000 USD Yearly USD 200000.00 250000.00 YEAR
Job Description & How to Apply Below
About Polymarket

Polymarket is the world's largest prediction market platform. We enable individuals to express views on real-world events by trading on outcomes across politics, economics, sports, culture, and current affairs. Built as a peer-to-peer marketplace with no centralized "house,", Polymarket aggregates diverse opinions into transparent, market-based probabilities that reflect collective expectations about the future.

About the Role

The Customer Experience team at Polymarket is small, high-output, and operating in a space where the questions agents answer, whether from a human or an AI, are genuinely hard. Markets, probabilities, resolution rules, and financial mechanics are not standard support territory. We work with an in-house team and outsourced partners, and right now the systems that keep quality consistent, knowledge accurate, and agents ramped quickly are being built in real time.

This role owns all three.

Your mandate is to make sure every agent, human or AI, gets the answer right the first time, and that when something goes wrong, it only goes wrong once. That means owning QA, knowledge and content, and learning and development as a single connected system, not three separate work streams. You will set the quality bar, maintain the knowledge that feeds both people and AI, and build the training that gets new agents to standard fast.

Then you will close the loop: QA findings become training, training gaps become content, and content keeps the AI accurate.

This is a builder role. Some of the infrastructure exists; most of it needs to be designed, implemented, and owned by you. You will also hire and lead the specialists who run these programs day to day. If you want a role where the system is already in place, this is not it. If you want to build the system and then run it at scale, it is.

What

You'll Do
  • Define the QA scorecard, run weekly audits across human and AI conversations, and calibrate scoring with in-house and BPO teams monthly so the quality bar is the same everywhere.
  • Build an AI-assisted QA program that reviews a materially larger share of conversations than traditional sampling allows, and use what it finds to drive action.
  • Own the help center, internal knowledge base, macros, and the knowledge inputs and prompts that feed our AI agents, keeping all of it accurate as products and policies change.
  • Design and run onboarding and ongoing training for in-house agents and BPO partners, tracking ramp time and holding both to the same standard.
  • Translate QA failure patterns into new training modules, updated content, or process changes so the same issue does not keep appearing in audits.
  • Build compliance review into QA workflows for regulated interactions, and report on results alongside standard quality metrics.
  • Hire, develop, and manage specialists across QA, content, and L&D as the team grows.
What We're Looking For
  • 6 or more years working in QA, knowledge management, or L&D inside a support organization, with real ownership over outcomes, not just execution.
  • A track record of building at least one of QA, content, or L&D from scratch, and demonstrated ability to raise the standard on the others.
  • Experience running programs across both in-house and outsourced teams, including calibration sessions and holding BPO partners to internal quality standards.
  • Strong writing skills: you can produce help center articles and training materials that agents actually read and use.
  • Hands‑on experience with QA platforms, an LMS, and a help center CMS. You know how these tools work and how to get the most out of them.
  • Comfortable with data: you track QA scores, ramp time, deflection rates, and CSAT impact, and you report on them clearly.
  • Experience managing and developing a team of specialists.
  • (Plus) Direct experience with AI-assisted or agentic QA tools, not just awareness of them.
  • (Plus) Background in fintech, crypto, or any regulated support environment where compliance review is part of the QA process.
Benefits
  • Competitive salary & equity
  • Unlimited PTO
  • Full Health, Vision, & Dental coverage
  • 401k match
  • Hardware setup: new Mac Book Pro, big display, & accessories
Pay Transparency

Base salary range: $200,000 to $250,000, plus equity and benefits.

This is a good-faith range for the level we're hiring at. Experience varies widely within a title here, so if your expectations fall outside it, reach out anyway. We're always happy to talk it through.

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