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Aspire is a Series C fintech company building a financial operating system for global founders, trusted by 50,000+ startups. The company combines banking, software, and automation into a single platform, backed by Y Combinator, Peak XV, and Lightspeed.
You will design, build, and ship AI systems that automate software quality across Aspire's engineering organization. This is a high-impact role where you own multiple interconnected systems:
**Key Ownership Areas:**
1. **AI Test Generation Pipeline**: Build an LLM system that reads product specs, identifies coverage gaps and testability issues, and generates automated tests. You'll own context retrieval across specs and codebases, prompt and agent design, evaluation frameworks, and feedback loops based on live test results. Take this from POC to production.
2. **Merge Guardrail**: The guardrail is already live in production, blocking merges when coverage is missing or critical bugs are detected. Improve its precision, scale it across all engineering tribes, and integrate it with the generation pipeline so it proactively creates missing tests rather than only blocking.
3. **Reliable Automation Tooling**: Build the intelligence layer behind automation, including synthetic test data generation, AI agents that explore and verify flows, automated failure classification, and risk-based test selection. Ensure every alert is accurate and actionable.
4. **Quality Platform Ownership**: Embed AI-assisted practices with QA engineers. Understand specs, code, and failure modes deeply. Contribute at design stage, not after release. In a regulated fintech serving 50,000+ businesses, quality gaps directly impact customers.
5. **Security Regression in CI**: Design and build automated security regression tests for high-risk API endpoints, ensuring every auth boundary is verified at merge. This is a MAS Singapore requirement and will be built from scratch.
**What You Bring:**
Proven experience shipping AI systems: you have built and deployed an LLM application, agent, developer tool, or automation that replaced real manual work. You understand failure modes like hallucinations, context limits, and evaluation gaps, and know how to address them.
Strong software engineering with a quality mindset. You write production code, design systems, and build tools used by other engineers. You understand test architecture, coverage, and failure analysis well enough to define what good testing looks like.
High standards: you address root causes rather than symptoms and treat production defects and flaky tests as system-level problems to eliminate.
Ownership and initiative: you identify problems, validate them with data, and propose solutions without waiting to be assigned.
Comfort with ambiguity: you are motivated by an evolving roadmap that starts with quality and extends to wider engineering workflows as the team learns what works.
**In Your First 90 Days:**
Become the go-to engineer for building quality into development workflows. Challenge at least one existing practice with data and propose a better approach. Review the codebase and identify the three biggest quality gaps based on data, propose solutions, and build tooling for at least one. Deliver a measurable improvement in quality via the test-generation pipeline, merge guardrail, automation reliability, or code review.
**Requirements:**
- 5+ years in software engineering with meaningful exposure to development, testing, quality, or developer tooling, preferably including a fintech or regulated-environment project
- Strong software engineering in TypeScript and/or Python, with experience building production services, internal tools, or developer platforms
- Hands-on experience building LLM applications, including prompt engineering, RAG or context retrieval, agents or tool use, and output evaluation (side projects, internal tools, or POCs count if shipped)
- Strong day-to-day use of AI coding tools and agentic workflows
- Solid understanding of test automation and test architecture; Playwright experience is a strong plus
- CI/CD experience (GitHub Actions, Jenkins), including building tooling that integrates at PR and merge stages
- Ability to read and reason about backend code, API contracts, and service boundaries
- Experience owning a system or product domain end-to-end
- Familiarity with financial workflows such as payments, KYB/KYC, and transaction processing is a strong plus
