Machine Learning Senior/Staff 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

• 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

• 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

Nice to have

• 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
• An 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)