Fractional CHRO
SylloTips
EUR 2k-3k / month
Posted on Nov 7, 2025
Fractional General Counsel / Legal Officer - SaaS B2B / AI startup
About SylloTips [Syllotips Homepage]
Imagine AI agents that continuously learn from a company’s top employees. At SylloTips, we transform undocumented expertise into dynamic, ever-adapting AI, bridging the gap between human know-how and enterprise systems.
Founded in Rome in 2023 and run by AI PhDs and veterans from Amazon, Google, The Fork, and Translated, we’ve been accelerated by Techstars and are now part of the Harvard Innovation Labs (finalists in the President’s Innovation Challenge).
Thanks to our unique “human-in-the-loop” approach, SylloTips is already trusted by leading telecom, insurance, and finance companies to supercharge customer support and sales.
Founding Team
Giorgio Barnabò (CEO/CSO): Ph.D. in AI, strong academic background in Statistics and Finance, former research scientist at Amazon Alexa. www.linkedin.com
Leonardo Martini (COO): Ph.D. in Data Science, solid academic background in Maths and Computer Science, former researcher at Harvard. www.linkedin.com
Simone Silvestri (CTO): Full Stack Engineer with 5+ years of experience in microservices architecture development. www.linkedin.com
Andrea Rossi (AI Applied Scientist): Ph.D in AI with 5+ years of working experience, including Google and Translated. www.linkedin.com
Giorgio Pagliaro (Tech Lead): M.Sc. in Computer Engineering with 12+ years of experience as a Full Stack Software Engineer. Expertise in leading development teams, working in startup environments and architecting and developing robust software solutions. www.linkedin.com
Songle Jin (Founding Engineer): M.Sc. in Computer Science & Engineering with 5+ years of working experience, including The Fork. www.linkedin.com
Qianfei Gu (Senior Product Designer): Product designer with 5+ years experience in B2B companies from startups to enterprises. www.linkedin.com
Leo Arcasenza (Customer Support): Background in sales and digital marketing with 3+ years of working experience in startups across France and Italy. www.linkedin.com
Role Overview
We’re seeking a Fractional General Counsel / Legal Officer (≈ 1–2 days per week) to own our legal strategy while we scale in Italy and expand internationally. You’ll be our single point of truth on corporate governance, commercial contracts, data privacy (GDPR & forthcoming EU AI Act), employment matters, IP, and fundraising. Reporting directly to the CEO, you’ll operate hands‑on in a fast‑moving startup, partnering with founders, sales, product, and finance to balance growth with compliance.
Key Responsabilities
Corporate & Governance
Maintain board and shareholder documentation, option plans, and corporate registers.
Advise on fundraising (convertible notes/SAFEs/equity) and liaise with external counsel when needed.
Commercial Contracts
Draft, review, and negotiate MSAs, DPAs, NDAs, reseller and partnership agreements with enterprise clients (Italian & international).
Standardise templates to accelerate the sales cycle while managing risk.
Regulatory & Compliance
Lead GDPR compliance (RoPA, DPIAs, SCCs) and prepare for the EU AI Act and other emerging frameworks.
Oversee trademark/IP strategy and open‑source licence compliance.
Employment & Contractor Matters
Advise on Italian labour law, international contractor agreements, and incentive plans (SOP/ESOP).
Risk Management & Policies
Develop and update internal policies (information security, ethics, whistle‑blowing) and conduct periodic trainings.
External Counsel Management
Select and coordinate specialist law firms in Italy and abroad, controlling budget and quality of advice.
Required Experience and Skills
Italian‑qualified lawyer with 5+ years PQE in corporate/commercial law (top firm or in‑house tech/SaaS preferred).
Demonstrable experience negotiating enterprise software or data‑processing agreements.
Deep knowledge of GDPR, privacy‑by‑design principles, and a keen interest in the EU AI Act and digital‑services regulation.
Fluent Italian and English communication (both drafting and negotiation).
Comfortable working fractionally/part‑time and juggling diverse topics independently.
Plus
Experience supporting VC fundraising rounds and cap‑table management.
Prior exposure to US or UK law (e.g., Delaware C‑Corp structures, transatlantic data transfers).
Familiarity with open‑source licences and software‑patent strategy.
Previous work in an early‑stage startup or scale‑up.
Interview Process
Phone Screening (15 min): Quick mutual fit check on availability, motivations, and high‑level expertise.
Follow‑up Interview (45 min): Deep dive into your background, notable deals, and startup experience.
Case Study – Contract Redline (45 min): Live mark‑up of a sample SaaS MSA + DPA to assess drafting, negotiation rationale, and risk prioritisation.
Technical Interview (45 min): Discussion of GDPR, AI Act readiness, corporate governance scenarios, and outside‑counsel management.
Behavioral Interview (45 min): Based on SylloTips’ core tenets, following a STAR model.
What We Offer
Engagement type: fractional (independent contractor or part‑time employment)
Compensation:
Monthly retainer €2k – €3k EUR (for ~4-5 days/month)
Additional hourly/project fees for ad‑hoc matters
Remote Work (from the EU)
Autonomy & Impact: Shape the legal foundation of a cutting‑edge AI company as we scale across Europe and beyond.
If interested, send your application to: hiring@syllotips.com
Ps. Feel free to apply even if your rates are higher than that!
