About the role
Skyway (by Duckbill) is seeking a Head of Engineering to own how the product gets built — the architecture, velocity, team, and technical decisions that will compound for years. This is a builder-first role: you will personally ship working capabilities every day and use that credibility to set the pace for the team.
What You'll Do:
- Ship daily and set the pace: personally ship working capabilities every day, identify and remove anything that slows shipping (tooling gaps, process bloat, unclear requirements, architectural bottlenecks). The team should be capable of shipping more in month 12 than month 6.
- Build the engineering team: set the engineering talent bar, hire, and grow engineers — raising their technical bar and building a culture where the team does the best work of their careers.
- Make architecture decisions that last: build on a stack and architecture that supports 10–50x growth in data and customers without fundamental rearchitecture. Make deliberate, documented decisions about what's built to last vs. intentional tech debt.
- Bring product ideas to the table: have strong opinions about product improvements based on what you see in the code, data, and customer behavior. Push back on product direction when warranted.
- Be a credible technical voice externally: participate in enterprise sales calls, customer onboarding, public promotional events, and investor meetings.
Technical Context: The product processes hundreds of millions of rows of billing data per customer per month, recalculates bills dynamically using contract and public pricing data, and builds a semantic layer translating cloud usage into business concepts. Core challenges include near-unbounded data cardinality, modeling pricing schemes for hundreds to thousands of vendors, and hiding complexity from customers through excellent product design.
Current stack: Python, Flask, ClickHouse, Airflow, React, TypeScript. The stack will evolve.