Demo

Lead / Senior Engineer - People Technology

Oscar Technology
Chicago, IL Full Time
POSTED ON 10/12/2026
AVAILABLE BEFORE 11/12/2026


Team: Infrastructure Development - People Technology
Employment Type: Permanent, Full-Time
Location: Chicago, IL - Hybrid, 3 days onsite per week
Compensation: $140,000-$180,000 base annual discretionary bonus


About the Company


A global technology-driven trading firm is building a new People Technology function within its Infrastructure Development organization.


The firm operates internationally across a range of financial markets and has a strong engineering culture focused on autonomy, innovation and solving complex problems.


The Opportunity


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




  • Own the technical roadmap and ongoing development of eight internal HR applications




  • Partner directly with Talent Acquisition, Talent Development, Talent Management and other HR teams




  • Translate business requirements and pain points into scalable technical solutions




  • Assess applications for technical debt, modernization opportunities and long-term support needs




  • Design, build and ship production features across the full stack




  • Establish engineering, support and stakeholder communication processes




  • Help define the team structure and support the hiring and mentoring of an additional engineer




  • Maintain strong standards around architecture, stability and engineering best practices




Required Experience




  • Strong full-stack software engineering background




  • Hands-on experience with Python, TypeScript/React and PostgreSQL




  • Experience owning multiple applications from roadmap through development and production support




  • Strong experience working directly with non-technical stakeholders




  • Comfortable operating with a high level of autonomy




  • Strong communication skills and the ability to balance technical delivery with stakeholder management




  • Able to work onsite in Chicago 3 days per week




Preferred Experience




  • Experience with FastAPI, Flask, Next.js, Ruby or Sinatra




  • Previous Technical Lead or Team Lead experience




  • Experience mentoring other engineers




  • Familiarity with HR technology, ATS, HRIS or enterprise system integrations




Technology


Python | TypeScript | React | PostgreSQL | FastAPI | Flask | Next.js | Ruby


Compensation & Benefits




  • $140,000-$180,000 base salary




  • Annual discretionary bonus




  • Medical, pharmacy, dental and vision coverage




  • 401(k) with discretionary company match




  • Short- and long-term disability




  • Life and AD&D insurance




  • HSA and FSA options





Oscar Associates Limited (US) is acting as an Employment Agency in relation to this vacancy.

Salary : $140,000 - $180,000

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