Founding Lead Engineer, People Technology

Drweng; Chicago (IL); On-site; USD 140,000 - 180,000; Full time

Benefits offered by this job

Discretionary annual bonus

Medical, dental, vision insurance

401k with employer match

Life and AD&D insurance

Job summary

DRW, a diversified trading firm headquartered in Chicago, seeks a Lead/Senior Engineer to launch and own the People Technology team. You will be the sole technical owner of eight HR-oriented applications, coding across a modern stack while shaping the team roadmap and partnering with HR stakeholders.

You will validate staffing assumptions, work with leadership, and build the team from scratch. This is not pure management; you will code and mentor, defining processes and culture from the start.

Qualifications

• Strong full-stack engineering background with hands-on experience across Python, TypeScript/React, and PostgreSQL.
• Proven ability to own and drive multiple applications end-to-end—from roadmap through delivery and support.
• Experience partnering with non-technical stakeholders to translate needs into technical solutions.
• Comfort operating with a high degree of autonomy as a founding role.
• Strong communication skills and a collaborative mindset with HR partners.

Responsibilities

• Own the technical direction and roadmap for eight HR-adjacent applications.
• Serve as the primary engineering contact for HR stakeholders and translate business needs into technical solutions.
• Assess tech debt, modernization opportunities, and alignment with engineering standards.
• Validate initial staffing model and help define the second engineering role.
• Write and ship production code across Python, TypeScript/React, Ruby, FastAPI, Flask, Next.js, PostgreSQL.
• Formalize support processes and operational workflows as the team matures.

Skills

Python

TypeScript/React

PostgreSQL

Ownership

Autonomy

Communication

Tools

Ruby/Sinatra

FastAPI

Flask

Next.js

Job description

DRW, a diversified trading firm headquartered in Chicago, seeks a Lead/Senior Engineer to launch and own the People Technology team. You will be the sole technical owner of eight HR-oriented applications, coding across a modern stack while shaping the team roadmap and partnering with HR stakeholders.

You will validate staffing assumptions, work with leadership, and build the team from scratch. This is not pure management; you will code and mentor, defining processes and culture from the start.