Rome-based SylloTips Raises €4.2M Funding In Pre-Seed Round

The round was led by Azimut via its ALIcrowd III and IV funds, with participation from The Techshop, Techstars, Cloud Accelerator, Leo Capital, and business angels.

Giorgio Barnabò, CEO and Co-founder of SylloTips ​AI: “Companies don’t need another chatbot: they need agents that know when to ask for help, learn from experts, and continuously improve. With SylloTips, agents enter processes, interact with existing systems, and rely on a governed, verifiable memory. That’s how you move from pilots to results.”

Founded in 2023 by Giorgio Barnabò (PhD in AI, ex-Amazon), Leonardo Martini (PhD in AI, ex-Harvard), and Simone Silvestri (ex-Ericsson), SylloTips integrates its AI-driven software into Microsoft Teams to help companies automate internal “competence centres,” with agents learning directly from employees.

Trusted by clients like EOLO, COIMA, Leonardo Assicurazioni, and Gruppo AB, the startup has reportedly converted all pilot projects into full production deployments.

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Vincenzo Esposito, CEO of Microsoft Italy and new SylloTips board member said: “Artificial intelligence is the next general-purpose technology, and it is reshaping the way we work. The rise of agents, executing tasks and orchestrating processes, has the potential to multiply impact on people, businesses and the economy. SylloTips’ multi-agent software is rooted in human capital, combining technology with the central role of people.”

A recent MIT study found that 95% of organisations see no measurable returns from generative AI, with only 5% of solutions progressing beyond pilot stages. While adoption is high, real transformation and value creation remain limited.

SylloTips identifies the root issue as the learning gap: AI systems often fail to adapt to context, retain feedback, or integrate into existing workflows. Their “human-in-the-loop” approach addresses this by embedding AI agents into Microsoft Teams, enabling employees across sales, customer service, operations, and IT to access and apply company knowledge in line with corporate policies.

When an AI agent lacks confidence, SylloTips automatically involves subject matter experts. Their input is captured, reviewed, and stored in a governed memory, creating a collective knowledge base that continuously enhances agent performance.

Nicoletta Mastropietro, former CIO of Leonardo, Vodafone, Banca Iccrea and A2A, and new SylloTips board member added: “In the world of generative AI, I see SylloTips as a true one-of-a-kind. Each agent is fully accountable: every interaction is tracked, every piece of data is verifiable. Information quality constantly improves with decisions supported by reliable sources and expert oversight. The impact on mission-critical processes is tangible: efficiency speed and reliability become the norm, quickly moving from pilot to production.”

SylloTips has delivered strong results in several areas: call centre support (reducing handling times and improving response consistency), field worker assistance (providing contextual procedures, checklists, and troubleshooting), and sales enablement (preparing offers and handling technical-commercial Q&A on complex catalogs).

Its multimodal capabilities allow seamless use of documents, images, and structured data, while multilingual support ensures easy adoption across multinational teams.

The ecosystem is another advantage: SylloTips is an official Microsoft partner, available on Azure Marketplace and MACC-eligible, streamlining procurement via pre-allocated Azure budgets.

Integration is straightforward, connecting with Salesforce, SAP, ServiceNow, Jira, Google Drive, Microsoft Copilot, and proprietary data lakes, preventing application silos and maintaining compliance with IT policies.

Maurizio Bobbio, former SVP at Oracle and new SylloTips board member said: “There are many reasons why I believed – and continue to believe – in SylloTips. First of all, the founders team is highly competent, ambitious, and well-balanced in their roles. The pain points addressed by the product are real and pressing across industries, which is why every client who piloted the system ended up purchasing it.

SylloTips adapts to context, improves with use, and integrates seamlessly with client processes and systems – qualities that make it both highly effective and very difficult to replace. I believe the commercial aggressiveness and speed with which SylloTips is moving, in Italy and beyond, are the key factors to achieving the big ambitions we all share.”

The new funding will accelerate R&D, enhancing AI agent modules, strengthening governed memory, and expanding integrations with popular tech stacks, while also boosting go-to-market efforts in telecom, insurance, banking, and defense.

SylloTips plans senior hires in AI and sales and is reinforcing its board with high-profile additions: Vincenzo Esposito (CEO, Microsoft Italy), Nicoletta Mastropietro (former CIO, Leonardo, Vodafone, Banca Iccrea, A2A), Maurizio Bobbio (former SVP, Oracle), and Lorenzo Congiu (Azimut).

Martin Olczyk, Managing Director of Techstars Transformative World Torino added: “Investing in SylloTips was one of the easiest decisions I’ve ever made as an investor. It was immediately clear that Giorgio and his team combine a rare Founder–market fit, strong execution ability, and a bold vision. From day one to today’s milestone, their progress has been remarkable. SylloTips is not only shaping the future of enterprise AI but proving that a world-class company canbe built in Italy. We’re proud to back them once again.”