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Forward Deployed Engineer

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: WithCoverage
Full Time position
Listed on 2026-01-12
Job specializations:
  • Software Development
    Full Stack Developer, Cloud Engineer - Software
Salary/Wage Range or Industry Benchmark: 150000 - 180000 USD Yearly USD 150000.00 180000.00 YEAR
Job Description & How to Apply Below

Location: New York, NY
Job Type: Full-Time

We protect the companies building the future—100's of brands like GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee—so they can move fast without compromise.

Instead of a stale brokerage model, we’ve built a new category: world-class risk advisors powered by proprietary technology. From next-generation defense contractors and advanced manufacturers to iconic consumer brands and hospitality leaders, we partner with ambitious businesses to give them the confidence to scale.

Founded by JD Ross (co-founder of Opendoor) and Max Brenner (Compound, Bain), With Coverage is disrupting a trillion-dollar industry from the inside out. We grew 10x last year while staying cash-flow positive, with backing from 8VC, Crystal Venture Partners, and other top investors.

We’re also the only brokerage that has built its own Agency Management System from scratch, giving us full control of our operations and a platform to automate more and more of the business with AI. It’s the foundation for transforming how risk is managed across the economy.

Why Join Us:
  • Grow Faster – We’re scaling fast, giving you outsized opportunities to learn, lead, and shape your career and the future of the company.
  • Work That Matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers.
  • Redefine an Industry – Insurance is one of the largest, slowest-moving markets. We rewrite the playbook with proprietary technology, automation, and AI.
  • Financial Rewards – We hire the best and invest in you. That means competitive comp, meaningful equity, and great benefits. We believe strongly in internal promotion, and lay out a plan for everyone's career growth.
About The Role:

As an Engineer on the With Coverage team, you will do more than just write code. You’ll own projects end-to-end – from scoping ideas to building, testing, and refining them with real users.

What You’ll Do:
  • We are looking for a Fullstack Engineer to join our team and help transform the trillion dollar insurance industry.
  • If you're thinking "I'm an experienced developer, but I want to play with LLMs a lot in the systems I build", then this is a great opportunity.
  • We'll show you opportunities for making an impact, and you'll own the outcome. We are a collaborative, high-agency team.
  • Develop and ship full-stack AI-driven projects from concept to production.
  • Iterate on your projects with internal users until they're loved and adopted.
  • Develop full-stack on a modern simple stack:
    Next.js + Tailwind 4, Express, Prisma Graph

    QL, Postgres, all deployed on Vercel and Render. Work with the latest LLM tools as they come out.
Who you are:
  • You have 3+ years of professional experience in full-stack development (4+ preferred).
  • You're passionate about applying LLMs to solve real business problems.
  • You like to learn by shipping and iterating. We ship a lot of prototypes!
  • You're comfortable up and down the stack, even if you specialize in a part of the stack.

For candidates based in the United States, the pay range for this position at the start of employment is expected to be between $150,000 – $180,000/year. Your exact offer may vary depending on multiple individualized factors, including market location, job-related knowledge, skills, and experience. Total compensation for this position may also include equity, quota incentives (for sales roles), and employee benefits.

In addition to cash compensation, With Coverage offers full-time employees a comprehensive Total Rewards package that includes equity grants.

What We Offer:
  • Competitive compensation including meaningful equity.
  • Flexible paid time off.
  • Comprehensive benefit plans for medical, dental, vision, life, and disability.
  • Flexible Spending Accounts (FSAs):
    Health Care FSA and Dependent Care FSA.
  • Commuter Savings Account.
  • Human Interest: 401(k) provider.
  • Time Off:
    Sick Leave, Family and Medical Leave, Flexible Time Off.
  • Paid Holidays:
    Observance of all major national holidays.
  • A curated in-office employee experience, designed to foster community, team connections, and innovation, that also includes catered lunches in the office on Fridays for in-office workers.
  • Collaborative, transparent, and fun culture.
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