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Head of Talent at AI-native insurance startup backed by Founders Fund & Lightspeed

May 25, 2026

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack's network. The next step is to speak to Jack. Job Title Head of Talent Salary Not Disclosed Company Description Founders Fund and Lightspeed-backed AI startup transforming the $280B P&C insurance market Job Description As the first dedicated talent hire, you will build the recruiting function from scratch for an AI-native company already at multi-7-figure ARR. You'll partner with the founding team to scale an elite group of engineers and researchers from 20 to 100+, defining the culture and organizational design of a generational insurance-tech platform. Location San Francisco, USA Why this role is remarkable <ul><li>Partner directly with founders from Palantir and top trading firms to scale an elite, high-intensity team from 20 to 100+ people.</li><li>Backed by premier investors including Founders Fund, Lightspeed, and Emergence Capital with exceptional product-market fit and multi-7-figure revenue in year one.</li><li>High-impact founding equity stake in a company replacing legacy fax-and-spreadsheet systems with end-to-end AI claims processing for a massive $280B industry. </li></ul>What You Will Do <ul><li>Own the full recruiting lifecycle from sourcing to closing world-class technical talent from top AI labs, trading firms, and tier-1 tech companies.</li><li>Design and implement the entire talent infrastructure, including interview processes, compensation frameworks, and organizational design strategies from the ground up.</li><li>Serve as a strategic talent advisor to the leadership team, ensuring every hire maintains the company's bar for elite technical excellence and high-ownership culture. </li></ul>The ideal candidate <ul><li>Proven track record of building or significantly scaling a talent function at an early-stage startup, ideally during the 20 to 100+ employee growth phase.</li><li>Exceptional ability to source and close elite technical talent, specifically engineers and AI researchers who typically gravitate toward top-tier labs or high-frequency trading firms.</li><li>Thrives in a high-intensity, in-person SF environment and possesses the strategic mindset to build systems without a playbook while moving at extreme startup speed. </li></ul>Who are Jack & Jill? Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support. And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate. Next steps Step 1. Visit the job listing. Step 2. Click 'Talk to Jack', or go straight there: https://www.jackandjill.ai/jobs/head-of-talent-at-ai-native-insurance-startup-backed-by-founders-fund-and-lights-30b70702-c7e3-4f9a-b9fc-acc64b85f568?utm_source=linkedin&utm_medium=job_post&utm_campaign=featured_role_30b70702-c7e3-4f9a-b9fc-acc64b85f568 Step 3. Talk to Jack so he can understand your experience and ambitions. Step 4. Jack will make sure Jill (the AI agent working for the company) considers you for this role. Step 5. If Jill thinks you're a great fit and her client wants to meet you, they will make the introduction. Step 6. If not, Jack will find you excellent alternatives. All for free. We never post fake jobs This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network. Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description. We appreciate this can make them look a bit suspect, but there isn't much we can do about it. Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.

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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...