Senior/Lead Software Engineer

About the role

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.

Responsibilities

• 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

• 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

Qualifications

• Computer vision/machine learning model development experience is a plus
• Experience with large-scale or real-time data pipelines is a plus
• Infrastructure-as-Code experience (Terraform, CDK, etc.) is a plus
• ML observability, data validation, or model deployment experience is a plus
• Familiarity with geospatial, imagery, or sensor-driven data is a plus
• A genuine interest in urban planning, accessibility, or civic technology is a plus

Skills

• Strong problem-solving skills
• Excellent communication and collaboration skills
• Ability to work independently and as part of a team

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)

Pay

$150,000 – $190,000 base salary, based on scope and experience

Schedule

Hybrid (Chicago)