As Head of Engineering, you will lead the development of Skyway, a platform managing massive data cardinality for AI labs and enterprises. This is a builder-first role where you will ship daily, set technical architecture, and scale a world-class engineering team while directly contributing to a stack featuring ClickHouse, Python, and Airflow.
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Head of Engineering at Duckbill
Duckbill is seeking a builder-first Head of Engineering to lead the development of Skyway, the financial operating system for the AI compute economy. Backed by $7.75M from Heavybit and Uncork Capital, you’ll join a team of domain experts who have spent seven years researching the world's most complex cloud billing problems. This San Francisco-based role offers the unique chance to architect a platform processing terabytes of data for AI labs and Fortune 500 companies. If you're a former founder or Director of Engineering who still loves shipping code daily and wants to scale a high-velocity team, this is your next career-defining move.
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Location
San Francisco, United States
Compensation
$200k-$250k + Equity
Company
Duckbill
Role overview
Enterprise B2B SaaS15 employees
We help companies negotiate, manage, and forecast cloud and AI contracts. We’ve worked with hundreds of companies and have supported the negotiation of tens-of-billions in cloud and AI contracts.
What you will do
- Lead by example as a builder-first executive, shipping production-ready code daily while removing technical bottlenecks and architectural hurdles for the team.
- Scale the engineering organization from the ground floor, setting a high talent bar and fostering a high-velocity culture focused on customer impact.
- Architect data systems using ClickHouse, Airflow, and Python capable of handling 50x growth in data volume without requiring fundamental re-engineering.
Who this is a fit for
- Proven experience as a Director of Engineering, VP, or founder who has successfully built and recruited high-performing engineering teams from scratch.
- Deep expertise in data infrastructure, including large-scale ETL/ELT pipelines, columnar storage, and managing high-cardinality datasets in complex environments.
- An "agentic" builder mindset who thrives on shipping daily, embraces AI-assisted development, and prefers rapid iteration over long-term planning cycles.
Why this role is remarkable
- Own the technical vision for Skyway, a platform processing terabytes of complex billing data for AI-native software companies and global enterprises.
- Join a well-capitalized team backed by Heavybit and Uncork Capital with an unfair advantage: seven years of proprietary research and a massive existing community.
- Transition from a boutique services firm to a high-growth SaaS product targeting a $47.5 billion public cloud market opportunity.
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.
I recruit from Jack’s network and make the intro when I spot a great match.And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.
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What happens next?
Jack’s an AI agent for job searching and career coaching. He works for you.
Jill is the AI recruiter working for the company. She recruits from Jack’s network.
If your profile’s a match and Duckbill wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.