AI Engineer
Content + Source + Freshness • 11 Dec 2025 • 95% confidence
Offer value
High value due to the cutting-edge AI technology focus, hands-on development opportunities, and potential for significant impact in a high-growth startup.
- Cutting-edge focus on AI technology.
- Disruptive software solutions in the market.
- Competitive salary with growth opportunities.
- Requires adaptability to new developments.
Pros
- Strong focus on AI technologies with high growth potential.
- Opportunity to shape innovative software solutions.
- Competitive compensation and engaging work environment.
Cons
- Young startup with inherent risks regarding stability.
- Fast-paced environment may lead to high stress.
- Role requires continual adaptation to new technologies.
Who it's for
Mid to Senior Career • Hybrid or Remote
Good fit
- Mid to senior-level engineers skilled in AI.
- Professionals eager to innovate in software development.
- Individuals looking for challenges in a fast-paced environment.
Not recommended for
- Junior engineers without substantial AI experience.
- Those who prefer highly structured work settings.
- Candidates not interested in ongoing learning and adaptation.
Motivation fit
Key skills
About the job
Who We Are
Checksum is a high-growth, startup revolutionizing software testing with AI-powered, self-healing QA automation.Checksum’s platform eliminates the need for manual test maintenance by automatically generating and adapting tests based on real user behavior. Engineering teams can now release code faster without sacrificing quality—and our traction proves it: we’ve tripled ARR in the last 9 months. We are backed by Leap Global Partners and were formed at super{set}, whose co-founders have over $1B in exits to Microsoft and Salesforce.
We’re looking for a builder who ships. You have hands on experience building with LLMs, shown through shipped features or serious prototypes. You have worked with prompts, function calling, tool use, structured outputs, evals and failure handling You turn ambiguous problems into iterative plans, wire up tools and feedback loops, and measure what matters. You are comfortable moving between prompt design, Python code, and product tradeoffs. You enjoy pairing with engineers and PMs, mentoring teammates, and owning outcomes in a dynamic startup environment.
This is a hybrid role, 4x a week, in the San Francisco Office
What You’ll Do:
- Design, build and operate AI agents that plan, act, observe and learn across browser, API and data tools
- Integrate models with tools such as Playwright, internal APIs, vector search, document stores and webhooks
- Create evaluation harnesses, golden datasets and automated regressions for reliability and safety
- Optimize latency, accuracy and cost using caching, routing, function calling, tool selection and streaming I/O
- Collaborate on product UX for agent feedback, interruptions, approvals and failure recovery
- Own the full lifecycle from prototype to production, including CI, experiments and on call rotations
What We’re Looking For:
- BSc in computer science or equivalent experience
- Ability to work independently, and solve problems based on clear goals
- Strong Python or TypeScript Skills
- Experience building evals, datasets and automated tests for ML or LLM systems
- Experience building agents that control browsers with Playwright or Selenium
- Knowledge of CI/CD, containerization and cloud deployments
- Exposure to retrieval augmented generation, planning and memory, multi agent orchestration and toolformer style designs
- Experience with Anthropic, OpenAI, Google and open source models such as Llama, plus model selection and routing
- Background in testing automation, QA engineering or developer tools
Benefits & Perks:
- A strategic role in shaping the growth trajectory of a cutting-edge AI startup
- Competitive salary, equity, and benefits package
- Lunch everyday you are in the office
- Monthly company happy hours
