Rome, September 22, 2025 — SylloTips, the Italian startup founded by Giorgio Barnabò (PhD in AI, ex-Amazon), Leonardo Martini (PhD in AI, ex-Harvard) and Simone Silvestri (ex-Ericsson), today announced the closing of a €4.2 million Seed round to accelerate the development and commercialisation of its human-in-the-loop AI agents. The round — one of the largest in Italy in 2025 — places SylloTips on a growth trajectory comparable to the most promising players in Silicon Valley.
The round, led by Azimut through its Azimut Eltif – Venture Capital ALIcrowd III and IV funds managed by Azimut Libera Impresa SGR, saw participation from existing investors The Techshop, Techstars, and Cloud Accelerator, and welcomed Leo Capital alongside several notable business angels. Legal matters were handled by Bonelli Erede with notarial support from Giovannella Condò (Milano Notai).
Having already earned the trust of strategic clients such as EOLO, COIMA, Leonardo Assicurazioni, and Gruppo AB, SylloTips is gaining recognition for the effectiveness and robustness of its solutions, with 100% of pilot projects converted into production implementations. Founded in Rome in 2023 and accelerated by Techstars Transformative World Torino in 2024, the startup won the SMAU Innovation Award and was a finalist in the President’s Innovation Challenge at the Harvard Innovation Labs in 2025.
The challenge: adopting generative AI in the enterprise
MIT recently described this as the “GenAI divide”: 95% of organizations see no measurable returns from generative AI, and only 5% of solutions move beyond the pilot stage. Adoption is broad, but transformation and tangible value creation remain limited.
The issue is not model power, but the learning gap: systems that don’t adapt to context, fail to retain feedback, and integrate poorly with existing workflows. It’s in closing this gap between pilots and real-world operations that SylloTips positions its solution.
The SylloTips solution
“Human-in-the-loop”: this is how SylloTips adapts AI to complex enterprise contexts. At its core lays a system of AI agents integrated into Microsoft Teams that supports professionals across key business functions (sales, customer service, operations, and IT) in accessing and applying product and process knowledge in line with company policies.
When — and this is the breakthrough — an AI agent is not sufficiently confident, humans and their expertise step back in. SylloTips automatically engages the company’s subject matter experts. Their interventions are learned by the AI agents, reviewed and consolidated, feeding into a governed memory — the company’s collective knowledge — that progressively improves AI agent performance. This way, the agents learn from humans, remain effective and reliable, explain their decisions, respect roles and policies, and improve with use.
Among the most successful use cases for SylloTips clients are call center support (reduced average handling times and greater response consistency), field worker assistance (contextualized procedures, checklists and troubleshooting on site), and sales enablement (offer preparation and technical-commercial Q&A on complex catalogs).
Its multimodal nature allows it to combine documents, images, and structured data, while multilingual support facilitates adoption in multinational organizations.
Ecosystem and integration for seamless adoption
Another key factor is the ecosystem. SylloTips is an official Microsoft partner, available on Azure Marketplace and already MACC-eligible, making procurement easier via pre-allocated Azure budgets. On the integration front, the software connects with major enterprise systems — Salesforce, SAP, ServiceNow, Jira, Google Drive, as well as Microsoft Copilot and proprietary data lakes — avoiding new application silos and respecting IT policies.
Though delivered as SaaS, its operating model resembles that of integration champions: co-design with the client, joint teams working on application integration and data quality, and shared goals of reliability and telemetry to measure real impact. This hands-on approach explains why pilots don’t remain showcases but become living systems in production.
Next steps: research, development, and growth
The new funding will support research and development — extending agent modules, strengthening the governed memory, and broadening connectors and integrations with widely used tech stacks — as well as go-to-market efforts in telecom, insurance, banking, and defense, alongside new senior hires in AI and sales. To guide strategy, the board is expanding with prominent figures: Vincenzo Esposito (CEO, Microsoft Italy), Nicoletta Mastropietro (former CIO of Leonardo, Vodafone, Banca Iccrea and A2A), Maurizio Bobbio (ex-SVP Oracle) and Lorenzo Congiu (Azimut).
Giorgio Barnabò, CEO and co-founder of SylloTips
“Companies don’t need another chatbot: they need agents that know when to ask for help, learn from experts, and continuously improve,” comments Giorgio Barnabò, CEO and co-founder of SylloTips. “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.”
Vincenzo Esposito, CEO of Microsoft Italy and new SylloTips board member
“Artificial intelligence is the next general-purpose technology, and it is reshaping the way we work,” says Vincenzo Esposito, CEO of Microsoft Italy. “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.”
Nicoletta Mastropietro, former CIO of Leonardo, Vodafone, Banca Iccrea and A2A, and new SylloTips board member
“In the world of generative AI, I consider SylloTips truly one-of-a-kind,” comments Nicoletta Mastropietro. “Each agent is fully accountable: every interaction is tracked and every piece of data verifiable. The quality of information constantly grows, with decisions supported by reliable sources and expert oversight. The impact on mission-critical processes is tangible: efficiency, speed, and reliability become the norm, moving quickly from pilot to production.”
Maurizio Bobbio, former SVP at Oracle and new SylloTips board member
“There are many reasons why I believed — and continue to believe — in SylloTips,” comments Maurizio Bobbio. “First, the founders team is highly competent, ambitious, and balanced in their roles. The pain points addressed by the product are specific and pressing across industries, which is why every client who piloted ended up buying. SylloTips adapts to context and improves with use, integrates with client processes and systems — qualities that make it both highly effective and very hard to replace. I believe the commercial drive and speed with which SylloTips is expanding in Italy and abroad are key to achieving the big ambitions we all share.”
Martin Olczyk, Managing Director of Techstars Transformative World Torino
“Investing in SylloTips was one of the easiest decisions I’ve ever made as an investor,” says Martin Olczyk. “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 also proving that a world-class company can be built in Italy. We’re proud to support them once again.”
Gianluca D’Agostino, Managing Partner at The Techshop
“We invested in SylloTips already at pre-seed, betting on the team’s skills and chemistry,” says Gianluca D’Agostino. “In just a few months we saw Giorgio, Simone, and Leonardo grow as entrepreneurs and radically evolve the product, incorporating feedback from early design partners. Our conviction strengthened as the customer base grew and adoption of the SylloTips suite received very positive feedback — a clear sign of the impact their technology is already having in the enterprise market, which we believe this round will accelerate.”
Guido Bocchio, Head of Venture Capital at Azimut Libera Impresa
“We are proud to support SylloTips and its exceptional team,” comments Guido Bocchio. “We deeply believe their vision, based on an innovative approach to artificial intelligence, is shaping the future of professional knowledge. This investment is not only a sign of trust in their project, but also a confirmation of our conviction that AI will radically transform the world.”
About SylloTips
SylloTips is the Italian software for AI agents orchestrated with human-in-the-loop and governed memory, natively built for Microsoft Teams. It integrates with major enterprise software and enables use cases in sales, marketing, customer service and operations. Founded in Rome in 2023. Techstars 2024, SMAU Innovation Award, finalist Harvard Innovation Labs 2025.
