---
title: 'Insurance Expert - AI Training & Evaluation at Weekday'
canonical: 'https://feeny.ai/job/insurance-expert-ai-training-evaluation-weekday-india-fw9rbnca2hm9'
type: 'job'
last_seen: '2026-10-18'
---

# Insurance Expert - AI Training & Evaluation at Weekday

- **Company:** Weekday
- **Location:** India
- **Employment:** contract
- **Work type:** remote
- **Posted:** 2026-10-08
- **Last confirmed live:** 2026-10-18
- **Apply:** https://jobs.lever.co/weekdayworks/e9bcc660-1732-4f33-86cc-7bad9ffd3f82

## Job description

This is an internal role at Weekday. Not a role by a client.

- Role type: Project-based / Contract
- Location: Remote
- Compensation: ₹20,000–25,000 per task
- Experience: 3+ years in underwriting, claims, or a closely related insurance role
- Hours: Flexible and task-based — no fixed working days

Weekday is an AI-native recruiting platform. We are backed by Y Combinator and Venture Highway (now General Catalyst). We have built the largest white-collar talent database in India and have built tools to run outbound recruiting campaigns to them.

We are now running an AI training and evaluation project as a YC-backed AI data lab, and we're looking for insurance experts to build and judge the tasks that advanced AI models get tested on.

## About Weekday

## Company Overview
- **One-liner**: Weekday is an AI-powered recruiting platform that automates outbound sourcing campaigns to help companies hire top technical talent.
- **Entity Type**: Private (Seed stage; $2.2M total funding)
- **Headquarters**: San Francisco, California, United States
- **Founded**: 2021
- **Founders**: Amit Singh (CEO & Co-founder), Chetan Dalal (CPO & Co-founder), Anubhav Malik (CTO & Co-founder), Sanjay Sivaraman (COO) [weekday.works](https://www.weekday.works/our-story)

## Core Business
- **Primary Industry**: Human Resources Services / AI-powered recruiting
- **Target Customers**: B2B; seed-stage startups to enterprises hiring for engineering and technical roles
- **Mission / Purpose**: "Make hiring more human" by using AI to handle repetitive tasks, giving recruiters more time for meaningful interactions [weekday.works](https://www.weekday.works/our-story)

## Products & Services
- **AI Recruiter (Outbound Sourcing Campaigns)**: Fully managed service that discovers, reaches out to, and pre-vets passive candidates via email, WhatsApp, and phone. Achieves 30–50% response rates (3–5x industry baseline). [weekday.works](https://www.weekday.works/faq)
- **AI People Search & Database Access**: Subscription model providing direct access to a verified database of 300M+ professionals across the US and India (covers ~80% of Indian white-collar workforce). Includes AI smart filters, AI-drafted outreach, and multi-channel automation. [weekday.works](https://www.weekday.works/faq)
- **Free Candidate Tools**: AI auto-apply, resume builder, ATS resume scorer, company salary data, and culture reviews. [weekday.works](https://www.weekday.works/faq)
- **Chrome Extension & 20+ API Integrations**: Fits into existing workflows and data pipelines. [weekday.works](https://www.weekday.works/faq)

## Market Standing
- **Valuation / Market Cap**: Not publicly available (private company)
- **Key Metric**: Total funding of $2.2M (seed rounds); 5M currently active users in their marketplace [weekday.works](https://www.weekday.works/our-story)
- **Notable Investors / Partners**: Y Combinator (W21), Venture Highway (led latest seed round) [linkedin.com](https://www.linkedin.com/company/weekdayworks)
- **Growth Signals**:
  - Headcount: 108 employees (+58.1% YoY) [linkedin.com](https://www.linkedin.com/company/weekdayworks)
  - LinkedIn followers: 576,069 (+84.5% YoY) [linkedin.com](https://www.linkedin.com/company/weekdayworks)
  - Active job postings: 87 (monthly growth +61.1%) [linkedin.com](https://www.linkedin.com/company/weekdayworks)
  - Ranked #1 on Product Hunt [weekday.works](https://www.weekday.works/our-story)

## Competitive Advantages
- **Massive Verified Database**: 300M+ professionals with verified work history and contact data, covering ~80% of the Indian white-collar workforce – a unique asset for passive candidate sourcing. [weekday.works](https://www.weekday.works/faq)
- **Multi-Channel Outreach**: Combines email, WhatsApp, and phone – channels that outperform inbound-only hiring, especially for passive talent (70% of workforce). [weekday.works](https://www.weekday.works/faq)
- **High Response Rates**: Consistently 30–50% (vs. industry baseline <15%), driven by mutual-fit matching and persistent follow-up. [weekday.works](https://www.weekday.works/faq)
- **Pre-Vetted Candidates**: Delivers candidates who have been matched, screened, and confirmed interested before reaching the hiring team. [weekday.works](https://www.weekday.works/faq)

## Strategic Focus
- **Expand Technical Hiring Dominance**: Purpose-built for engineering roles, serving companies like CRED, Enterpret, and Utopia Labs. [weekday.works](https://www.weekday.works/faq)
- **Dual Engagement Models**: Contingency (white-glove, 15% of salary) and Subscription (database + outreach credits) to serve both small teams and in-house recruiting departments. [weekday.works](https://www.weekday.works/faq)
- **Continued AI Investment**: AI-driven candidate discovery, messaging optimization, and resume screening remain core differentiators.

## Why Work Here
- **Fast-Growing YC Startup**: Y Combinator (W21) backing, strong headcount and follower growth, and high demand for technical hiring solutions.
- **Global & Remote-Friendly**: Workforce distributed across 6 countries (India, US, UK, Qatar, Thailand, Spain); offices in San Francisco and Bengaluru. [linkedin.com](https://www.linkedin.com/company/weekdayworks)
- **Engineering & Product Culture**: Founders include CTO Anubhav Malik; technical roles are central to the product (Backend, Data Engineering, QA). [linkedin.com](https://www.linkedin.com/company/weekdayworks)
- **Active Hiring**: 87 open positions across sales, engineering, operations, and more – strong signal of growth and opportunity. [linkedin.com](https://www.linkedin.com/company/weekdayworks)
- **Impactful Mission**: Using AI to eliminate recruiter drudgery and increase human connection in hiring.

## Sources
1. [jobs.lever.co](https://jobs.lever.co/weekdayworks)
2. [weekday.works](https://www.weekday.works/our-story)
3. [linkedin.com](https://www.linkedin.com/company/weekdayworks)
4. [weekday.works](https://www.weekday.works/faq)
5. [ycombinator.com](https://www.ycombinator.com/)

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