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# Lead / Senior Engineer - People Technology

- **Company:** Oscar Technology
- **Location:** Chicago, IL, United States
- **Experience:** Expert
- **Salary:** $140,000.0 - $180,000.0
- **Contract:** Permanent contract
- **Skills:** Applicant Tracking Systems, Application Portfolio Management, Human Resources Information System (HRIS), Python (Programming Language), PostgreSQL, Ruby, Next.js, TypeScript, Enterprise Software Applications, ReactJS, Flask (Web Framework), Technical Debt, Fastapi, HR Software, Production Code, Sinatra (Software)
- **Published:** October 5, 2026
- **Apply:** https://www.dice.com/job-detail/89a51b0b-6d3f-496d-b10e-d831ff1d22a5

## About the Role

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Strong full-stack software engineering background
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Hands-on experience with Python, TypeScript/React and PostgreSQL
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Experience owning multiple applications from roadmap through development and production support
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Strong experience working directly with non-technical stakeholders
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Comfortable operating with a high level of autonomy
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Strong communication skills and the ability to balance technical delivery with stakeholder management
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Able to work onsite in Chicago 3 days per week

Preferred Experience

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Experience with FastAPI, Flask, Next.js, Ruby or Sinatra
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Previous Technical Lead or Team Lead experience
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Experience mentoring other engineers
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Familiarity with HR technology, ATS, HRIS or enterprise system integrations

## Description

The company is launching a new People Technology team to provide dedicated engineering support to its HR organization.

The team will own a portfolio of eight internal applications supporting areas including recruiting, onboarding, talent development and employee engagement.

As the founding engineer, you will take technical ownership of this application portfolio while acting as the primary engineering partner to HR. This is a hands-on leadership role where you will continue writing production code while shaping the roadmap, improving existing systems and helping build the team from the ground up.

Responsibilities

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Own the technical roadmap and ongoing development of eight internal HR applications
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Partner directly with Talent Acquisition, Talent Development, Talent Management and other HR teams
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Translate business requirements and pain points into scalable technical solutions
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Assess applications for technical debt, modernization opportunities and long-term support needs
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Design, build and ship production features across the full stack
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Establish engineering, support and stakeholder communication processes
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Help define the team structure and support the hiring and mentoring of an additional engineer
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Maintain strong standards around architecture, stability and engineering best practices