Senior/Lead Software Engineer

DeepWalk

Lead Software Engineer at DeepWalk setting technical direction for automated sidewalk inspection. Focused on large-scale imagery and production ML systems with a collaborative team.

Posted 5/1/2026full-timeChicago • Illinois • 🇺🇸 United StatesSenior💰 $150,000 - $190,000 per yearWebsite

Tech Stack

Tools & technologies

AWSAzureCloudDistributed SystemsGoGoogle Cloud PlatformJavaPythonTypeScript

About the role

Key responsibilities & impact

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 best practices around deployment, observability, system reliability, and scalability
Act as a senior individual contributor and mentor, helping raise the technical bar across the engineering team
Work closely with the CEO and operations team to turn business needs into clear technical priorities

Requirements

What you’ll need

5+ years of experience, ideally with strong experience at a growth stage startup
Demonstrated ability to translate ambiguous business requirements into long term technical goals
Experience owning system architecture and influencing technical decisions across teams
Fluency in at least one modern backend language (Python, Java, TypeScript, Go, etc.)
Strong understanding of system design, scalability, and distributed systems
Experience with cloud platforms such as AWS, GCP, or Azure

Benefits

Comp & perks

$150,000 – $190,000 base salary, based on scope and experience
Equity
Unlimited PTO (most of our team takes 3–4 weeks per year)
Health insurance
401(k) with ~4% match (100% on first 3%, 50% on the next 2%)
Convenient office location in The Loop
Hybrid work environment (typically 2 days in-office)

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

PythonJavaTypeScriptGosystem designscalabilitydistributed systemsdata pipelinesgeospatial datavisual data

Soft Skills

leadershipmentoringcommunicationcollaborationproblem-solving