VP of Engineering

About Callimacus

At Callimacus, we‘re working to change how people interact on the web. For the past 30 years, the user experience as we know it has been anchored to a typographic paradigm — predefined navigation trees of pages, sections, and menus — established in the Nineties when the web was born.

As the way people get informed, entertained, and shop evolves, traditional websites and interfaces are losing relevance, and the tools available limit the creative evolution of digital experiences. Callimacus was born from the conviction that the whole web experience can and should be reinvented.

So we built the engine for a different kind of digital experience. Callimacus is a multi-agentic platform that plugs into a company’s existing stack and reads multi-dimensional signals to understand what a visitor wants in the moment. Then, in milliseconds, our proprietary technology composes the entire interface around that intent, selecting the most relevant content and components as the person interacts.

Callimacus was founded in 2024 with the early backing of Brunello Cucinelli — one of our first investors, and now one of our customers. We launched in January 2026 to strong organic interest from enterprise customers, and recently raised from Salesforce Ventures the largest AI investment they have made in Italy, and one of their most significant in Europe.

We are a small, product-focused, founder-led team. We work on hard problems that haven‘t been solved before — by us or anyone else — and the people who join now get to solve them. We move fast, with high agency and strong ownership.

Callimacus is in production with demanding enterprise customers, the team is growing fast, and the founders are still deeply technical and deeply involved. Your job is not to take engineering away from them — it‘s to build the organization that lets a founder-led product ship faster as it grows: the people, the practices, and the pace.

• Own delivery. Turn a roadmap that gets redefined mid-week into a team that ships fast without burning out — process as light as possible, but no lighter.
• Grow the team. Partner with our Founding Recruiter to hire exceptional engineers, then make them better: coaching, feedback, and growth paths.
• Own how decisions get made. Architecture stays a shared, founder-involved conversation — you own how technical decisions are proposed, reviewed, and shipped, so speed survives scale.
• Build the engineering culture deliberately. Ownership, invention, and high standards — turned from founding-team instinct into durable practice.
• Stay technical. This is a small team. You’ll still read code, review designs, and be in the room when production misbehaves.

These are the same for every role at Callimacus. We hire people who get the job done and care about the end result — the product, the experience, the people using it.

• Ownership. You feel deeply responsible for your work and behave accordingly — from design through production and after. You don‘t wait to be told what to do; you see problems and act. “It’s not my job” is not part of your mindset.
• Invention. You light up at hard problems and are creative at finding solutions. You experiment, get your hands dirty, and land things. You hold very high standards and always look for ways to improve.
• Team-oriented. You‘re someone others can count on. You support the best idea even when it’s not yours, disagree productively, give and take feedback, share credit, and take on unglamorous work when that‘s what the team needs.

The craft bar for this role: You’ve led engineering teams of roughly 10–30 through a fast-growth phase, hired and managed senior engineers, and stayed close enough to the code to keep credibility with them. Startup experience strongly preferred.

We‘re early, and nobody is strong in all of these — we don’t expect you to be. Depth in two or three, plus curiosity about the rest, is what wins. If that‘s you, apply even if you don’t tick every box.

• Scaling a team from ~5 to ~30 engineers
• Hiring senior and staff engineers while keeping the bar high
• Delivery in fast-changing, founder-led environments
• Platform, SDK, or AI product background
• Enterprise customers and reliability commitments
• Hands-on TypeScript / AWS background

• Led engineering through a Series A→B phase
• Built engineering hiring and onboarding processes from scratch
• Experience with AI/ML products in production

We‘ll ask a lot of you, and we give a lot in return. We want Callimacus to be a place where talented, driven people flourish, and we take that commitment seriously. A few things you’ll find (and there‘s more):

• A product that will light you up. You’ll work at the frontier of what AI can do today, on problems nobody has solved before — which means most weeks you‘ll be reasoning from first principles rather than looking up how it’s done. What you land becomes the way it works.
• An exceptional opportunity for growth. You‘ll work directly with the founders in a small, senior, talent-dense team, with high agency from day one, and play an essential role in the growth of the company.
• Top-of-the-Italian-market salary and equity. You’ll own a real piece of what you‘re building, aligning your growth with the company’s long-term success.
• Amazing offices in the centre of Milan. In the Moscova neighbourhood, one of the liveliest areas in the city and twenty minutes from anywhere.
• Top-of-the-market health insurance. Comprehensive cover, for you and the people who depend on you.
• A welfare budget you decide how to spend. Gym, mental health, museums, courses, travel — whatever actually makes your life better.
• Genuinely good food all day. High-quality, restaurant-level meals, including breakfast, lunch, and all-day snacks.

We believe working side by side leads to faster progress, stronger ramp-up, and a culture built around community. For the next year we have decided to be in-person first. We‘ve invested in making our workplace worth coming to, and we’re happy to support your commuting. And we don‘t work by tickets: priorities get redefined often, sometimes mid-week, and you’ll need to be comfortable with that. If you‘re set on remote or on a settled roadmap, this isn’t your role. If you want to be in the room while the platform takes shape, we‘d like to meet you.

Location: On-site, central Milan (Moscova area)

Stack: Full-stack TypeScript (Node.js, React), AWS, RAG/LLM/agent orchestration

Experience: 10+ years, including 3+ leading engineering teams

Gross annual salary: €90–120k, plus significant equity (to validate against market)