About Blackboard

At Blackboard we’re building a portfolio of AI-native consumer apps: AI is reshaping how people use day-to-day software, and we’re participating in the revolution.

We’re growing extremely fast (0 → €1M ARR in just 10 months) with a small team of incredibly young people (median age is 24!) who love to build and ship things.

We got started by launching a leading education app in Italy: Kiwi AI, used by 1.3M+ students in Italy and Spain. We’re currently expanding across Europe and launching 2 more apps before the end of the year.

The role

AI workflows are the heart of Kiwi: they turn students’ documents into quizzes, summaries and study material. Your mission is to own it full-time: striving everyday to increase quality for 1.2M+ students.

You’ll own a core piece of the product end-to-end.

What you’ll work on

- Own AI workflow quality. Monitor quality scores for exam prep, quizzes and all other features, and treat them as your product metric.
- Build LLM-powered APIs. For tutoring workflows like homework help, step‑by‑step explanations, exam prep and much more.
- Find the weak spots. Segment our document data to discover where workflows underperform.
- Experiment relentlessly. A/B-test models and features, iterate on prompts and routing, and ship what wins.
- Design robust architecture. Design architecture, RAGs, databases, queues, error handling while optimizing everything for speed, cost and reliability.

What we look for

- Strong AI-workflow experience. You’ve built and shipped LLM-powered systems in production.
- Ownership. You take a problem and solve it independently, from idea to production. We expect you to become the mini-CEO of workflow quality.
- Drive. You’re extremely ambitious,



and speed and reliability are both the standard, not a trade-off.
- First principles thinking. You question complexity, structure your ideas sharply, and bring your own opinion, especially when it goes against everyone’s beliefs.

Requirements

- Minimum 3 years of experience working on LLM workflows
- Strong general backend engineering skills
- You are based in or near Milan, or open to relocating
- Start date as soon as possible

Technologies we use

- TypeScript
- PostgreSQL
- BullMQ
- PostHog
- Sentry
- Docker
- Codex & Claude Code

What we offer

- An exceptional opportunity for growth. We’re a fast-growing startup; our priority is to help people thrive and quickly grow into team-leading roles.
- Entrepreneurial teams. Our hiring bar is very high; you’ll work in small, autonomous, result-oriented teams with some of the most hard-working people in consumer apps.
- Full ownership. You call your own shots and take accountability for your decisions.

Selection process Apply through our Notion form

Screening by our technical team, within days

Take-home assignment: you’ll have 96 hours (OR LESS, to confirm) to complete it

Technical interview to review and discuss your assignment together

Behavioral interview

Final interview

Written offer, valid for 5 calendar days only

We prioritize signals of excellence over credentials and years of experience. So, if you’re excited about the opportunity and believe you could excel in this role, please apply and don’t self-reject.

Before you apply

Blackboard is a demanding environment, and we keep ourselves to a high standard. It leads to extraordinary learning and career growth but it requires real commitment. We expect you to spend most days in our Milan office, regardless of your long-term work location.

📌 AI Engineer (Milano)
🏢 Blackboard Studio
📍 Milano