Lead Software Engineer

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 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

What Success Looks Like (First 3–6 Months)

• Build a strong understanding of our current systems, processes, applications, and data pipelines

• Identify the biggest scaling, reliability, and maintainability gaps as we grow

• Increase the delivery speed of processed data

• Become a trusted technical partner to leadership

What We’re Looking For

Required

• 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

Nice to Have

• Computer vision/machine learning model development

• Experience with large-scale or real-time data pipelines

• Infrastructure-as-Code experience (Terraform, CDK, etc.)

• ML observability, data validation, or model deployment experience

• Familiarity with geospatial, imagery, or sensor-driven data

• A genuine interest in urban planning, accessibility, or civic technology

Compensation & Benefits

• $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)

DeepWalk participates in the federal E-Verify program to confirm the employment eligibility of all newly hired employees.

DeepWalk is an Equal Opportunity Employer and is committed to building a diverse and inclusive workplace. We do not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, or gender identity), national origin, age, disability, genetic information, veteran status, or any other legally protected status.

In accordance with applicable laws, DeepWalk provides equal pay for equal work and complies with all federal, state, and local pay transparency and compensation requirements.