
Head of Software Systems
6 days ago
This is a unique opportunity to join our ambitious AI-native company in the prop commerce space.
As a tech maverick who prefers coding over calendar invites and prototypes before pontificating, you will be responsible for turning hard, ambiguous problems into robust systems with real users.
We need someone who can personally solve complex pieces first, then turn those solutions into reusable patterns that the team can scale.
If you've ever thought, 'I could build that in a week,' and then actually did - you'll thrive here.
The ideal candidate will have hands-on experience with gen-AI, strong systems thinking, security and privacy instincts, and excellent written communication skills.
- Design and implement gen-AI services (prompt orchestration, retrieval, tool/function calling, streaming UX) with evaluation and guardrails.
- Build reliable ingestion/processing pipelines, storage, and delivery with strong observability and cost control.
- Implement consent-driven flows, signed links/tokens, rate-limits, audit trails, and abuse prevention.
- Ingest and normalize external data, model entities/relationships, and expose a clean query layer for apps and partners.
- Ship crisp, modern UIs and APIs for internal/external stakeholders, with performance and reliability budgets.
- Manage logs/metrics/traces, automated tests, incident runbooks, and a sane release cadence.
Key Responsibilities include designing and implementing gen-AI services, building reliable pipelines, and managing logs/metrics/traces.
Success Metrics include shipping demos weekly, releasing bi-weekly, and teaching by doing.
Your ToolkitYou will have access to a range of tools including TypeScript/Node, Python, React/Next.js, Postgres/Supabase, Cloudflare/Vercel, Redis, and object storage + CDN.
A nice-to-have toolkit includes Framer/WeWeb/Lovable for rapid UI and Firebase where it fits.
Requirements- 6-10+ years building production systems as the primary builder (titles < commits). Exceptional earlier-career builders welcome with proof.
- Evidence of turning ambiguous product problems into working software in days, not quarters.
- Hands-on gen-AI experience (retrieval, tools, streaming, evals) with real users — and lessons from failures.
- Strong systems thinking: data models, consistency trade-offs, perf budgets, failure handling.
- Security and privacy instincts: PII handling, consent, audit trails, regulatory awareness.
- Excellent written communication: crisp docs, READMEs, runbooks.
Start as Founding Head of Engineering (IC). As we scale, choose either:
- Principal/Distinguished IC track (maximize technical leverage), or
- CTO/VP Eng path once a team exists and needs management.
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