Fractional General Counsel
SylloTips
Legal
Posted on Nov 7, 2025
Privacy & Cybersecurity Expert / Consultant (Compliance & AI Governance) - SaaS B2B / AI startup
Team
CISO
Function
Security & Compliance
Level
Mid
Status
Live
Priority
P2
Location
Remote
Hiring Manager
Recruiter
2 more properties
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 searching for a Privacy & Cybersecurity Expert / Consultant (Freelance) to lead SylloTips’ compliance, security, and data‑protection programs. You will design, implement, and continuously improve the controls and documentation needed to obtain and maintain certifications such as ISO 9001, ISO 27001, SOC 2 Type II, and ensure full GDPR and AI Act compliance.
You will collaborate with Engineering, Product, and Operations to embed privacy‑by‑design and security‑by‑default principles across our AI‑driven SaaS platform, while acting as the primary liaison with auditors, customers, and regulators.
Key Responsabilities
Certification Ownership
Drive end‑to‑end readiness, audits, and renewals for ISO 9001, ISO 27001, SOC 2 Type II, and other relevant standards.
Maintain an Information Security Management System (ISMS) and Quality Management System (QMS) in line with certification requirements.
Privacy & Data Protection
Serve as internal GDPR lead (or designated DPO if qualified), performing data‑flow mapping, DPIAs, and vendor assessments.
Draft, review, and update privacy policies, data‑processing agreements, and incident‑response playbooks.
Risk & Security Governance
Run periodic risk assessments and security posture reviews; track remediation plans with clear ownership and deadlines.
Define security awareness training and oversee phishing‑simulation or similar programs for employees.
Customer & Vendor Trust
Respond to security questionnaires, due‑diligence requests, and contractual clauses from enterprise prospects.
Evaluate and monitor third‑party vendors for compliance with our security and privacy standards.
Continuous Improvement
Stay on top of evolving EU/US regulations (NIS2, AI Act, CCPA, etc.) and advise leadership on impact and roadmap changes.
Recommend pragmatic process and tooling enhancements that balance risk reduction with startup agility.
Required Experience and Skills
5+ years in information security, privacy, or compliance roles, preferably within B2B SaaS or cloud‑native environments.
Proven track record leading at least one full‑cycle ISO 27001 or SOC 2 Type II certification project.
Deep understanding of GDPR requirements and hands‑on experience operationalising them (records of processing, DSARs, etc.).
Familiarity with ISO 9001 principles and integrating quality and security management systems.
Ability to run risk assessments and translate technical controls into business‑friendly language for non‑technical stakeholders.
Fluency in Italian and excellent English communication (written & spoken).
Plus
Recognised certifications (e.g., CIPP/E, CISSP, ISO 27001 Lead Implementer/Auditor).
Experience with AI/ML‑specific security or data‑governance challenges.
Previous work in early‑stage startup environments where you owned “everything security & privacy”.
Interview Process
Phone Screening (15 min) — Quick mutual fit check on availability, freelance model, and core expertise.
Follow‑up Interview (45 min) — Discuss your past compliance projects, stakeholder management, and tooling.
Practical Case Study (45 min) — Walk us through how you would scope and execute ISO 27001 + SOC 2 Type II for SylloTips; expect open questions on risk prioritisation and resource allocation.
Technical Deep‑Dive (45 min) — Drill into GDPR, secure development lifecycle, and incident‑response processes.
Behavioral Interview (45 min): Based on SylloTips’ core tenets, following a STAR model.
What We Offer
Engagement type: freelance / contract (part‑time or project‑based, negotiable).
Compensation: competitive daily or project rate, with performance bonus linked to certification milestones.
Remote Work (from the EU)
High Impact: Own the entire trust & safety charter of a fast‑growing AI startup working with tier‑one enterprises.
Collaboration with Experts: Work directly with a world‑class team of AI PhDs and seasoned engineers.
If interested, send your application to: hiring@syllotips.com
Ps. Feel free to apply even if your rates are higher than that!
