AI Software Engineer Intern

June 22, 2026

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<h2>ABOUT OUTMARKET</h2>Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output.The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us.WHAT YOU’LL GET<ul style="min-height:1.5em"><li>A high-impact role with ownership from day one.</li><li>Competitive compensation and meaningful equity.</li><li>Direct collaboration with founders and real users.</li><li>Remote-first flexibility.</li><li>The opportunity to help build an AI-native product from the ground up.</li></ul><h2>ABOUT THE ROLE</h2>A hands-on internship building real, customer-facing AI features alongside our engineering team. You will ship production code, not throwaway prototypes, and see your work reach real insurance customers.WHY THIS ROLE<ul style="min-height:1.5em"><li>Ship real features in an AI-native product from week one.</li><li>Learn directly from founders and experienced engineers.</li><li>Work across the stack, including AI workflows, backend, and frontend.</li></ul>WHAT YOU’LL DO<ul style="min-height:1.5em"><li>Build and test features that use LLMs, structured data, and document processing.</li><li>Pair with engineers to take tasks from idea to shipped.</li><li>Investigate real customer data problems and turn them into product improvements.</li></ul>WHAT WE’RE LOOKING FOR<ul style="min-height:1.5em"><li>Pursuing or recently completed a CS or related degree.</li><li>Solid programming fundamentals (Python and/or JavaScript/TypeScript).</li><li>Genuine curiosity about applied AI and a strong learning mindset.</li></ul>BONUS IF YOU HAVE<ul style="min-height:1.5em"><li>Personal/academic projects with LLMs or data pipelines.</li><li>Exposure to React, SQL, or cloud tooling.</li></ul>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...