Lead Software Engineer

Lead Software Engineer Hybrid (Chicago) What You’ll Do 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 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. #J-18808-Ljbffr