Lead Software Engineer

About this role

About DeepWalk

DeepWalk is a fast-growing venture that helps cities keep people safe using computer vision to map and monitor their sidewalks. We have ongoing contracts with cities, universities, and engineering firms.

In the past year, we’ve processed thousands of miles of sidewalk across 20+ states, generating millions of labeled data points used in real-world infrastructure decisions. We’ve raised $4.1M, recently closed a $2.1M seed round led by Enable Ventures, and we currently generate 7-figure revenue helping communities across America.

Lead Software Engineer

$150,000 – $190,000 base salary + equity · Hybrid (Chicago)

We’re hiring a Lead Software Engineer to set the technical direction of DeepWalk’s platform for automated sidewalk inspection. This role is focused on tackling high-impact, open-ended problems around large-scale imagery, production ML systems, and data pipelines that handle hundreds of terabytes of data.

You’ll play a key role in how we process, analyze, and deliver insights from millions of images, supporting cities as they work to build safer, more accessible infrastructure.

In this role, you’ll work closely with a handful of experienced engineers, help set technical direction, and establish patterns the team can scale with.

Our core stack today includes Python-based CV/ML systems running on AWS, with data pipelines and services designed to handle large volumes of imagery and geospatial data. We also develop and support customer facing web and mobile applications for our users to scan and view their data.

What You’ll Do

As a Lead Engineer at DeepWalk, you’ll have significant ownership over the systems we build and how we build them. You will…

• Set the technical direction for scaling out our platform
• Design and improve data pipelines that process thousands of miles of sidewalks and millions of images
• Lead architectural decisions for handling hundreds of terabytes of geospatial data and visual data
• Set and evolve bes...