Founding Lead Engineer, People Technology

DRW Holdings, LLC.; Chicago (IL); On-site; USD 140,000 - 180,000; Full time

Benefits offered by this job

Health insurance

401k match

Dental coverage

Vision coverage

Job summary

DRW in Chicago is seeking a Lead / Senior Engineer to be the founding member and technical leader of the People Technology team. You will own the eight HR-adjacent applications from roadmap to production, while coding hands-on and shaping the team from scratch.

You will partner with HR to translate business needs into scalable solutions, assess tech debt, and establish processes as the team grows, including staffing the second engineering role.

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 directly with non‑technical business stakeholders to translate needs into technical solutions.
• Comfort operating with a high degree of autonomy — this is a founding role where you will define processes, priorities, and team culture from scratch.

Responsibilities

• Own the technical direction and roadmap for a suite of eight HR‑adjacent applications, balancing maintenance and stability with new feature development driven by HR partner priorities.
• Serve as the primary engineering point of contact for HR stakeholders — embedding in their planning sessions, understanding their pain points, and translating business needs into technical solutions.
• Conduct a comprehensive assessment across all applications — evaluating tech debt, modernization opportunities, support burden, and alignment with engineering standards.
• Validate the team's initial staffing model and partner with leadership to define and fill the second engineering role.
• Write and ship production code across a diverse stack (Python, TypeScript/React, Ruby, FastAPI, Flask, Next.js, PostgreSQL) while maintaining high quality standards.
• Formalize support processes, stakeholder communication channels, and operational workflows as the team matures.

Skills

Python

TypeScript/React

PostgreSQL

Owning multiple apps

Communication

Tools

Ruby

FastAPI

Flask

Next.js

Job description

DRW in Chicago is seeking a Lead / Senior Engineer to be the founding member and technical leader of the People Technology team. You will own the eight HR-adjacent applications from roadmap to production, while coding hands-on and shaping the team from scratch.

You will partner with HR to translate business needs into scalable solutions, assess tech debt, and establish processes as the team grows, including staffing the second engineering role.