Senior/Staff Software Engineer – Machine Learning

DeepWalk

Senior/Staff Software Engineer leading technical direction on DeepWalk's computer vision platform for sidewalk inspection. Focused on production ML systems and data pipelines, collaborating with experienced engineers.

Posted 4/29/2026full-timeChicago • Illinois • 🇺🇸 United StatesSenior💰 $150,000 - $190,000 per yearWebsite

Tech Stack

Tools & technologies

AWSAzureCloudDistributed SystemsGoGoogle Cloud PlatformJavaPythonTypeScript

About the role

Key responsibilities & impact

Own the lifecycle of our computer vision models, including training, evaluation, deployment, and iteration
Improve model performance in real-world conditions (noise, edge cases, data drift)
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 and visual data, including storage layout, pipeline reliability, and inference performance
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, including direct ownership of production ML or computer vision systems (training, deployment, and ongoing operation)
Experience taking models from training → production → monitoring → iteration in a real-world environment
Experience owning system architecture and influencing technical decisions across teams
Experience deploying ML systems in real-world production environments
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
Comfort working in a startup or growth-stage environment with changing requirements

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

computer visionmachine learningdata pipelinesmodel trainingmodel evaluationmodel deploymentsystem architecturesystem designscalabilitydistributed systems

Soft Skills

mentoringleadershipcommunicationcollaborationproblem-solving