Account Executive
SylloTips
Sales & Business Development
EUR 45k-60k / year + Equity
Posted on Nov 7, 2025
Enterprise Account Executive - SaaS B2B / AI startup
Team
Sales
Function
Sales
Level
Mid
Status
Live
Priority
P2
Location
Italy
Hiring Manager
Giorgio Barnabò
Recruiter
Leonardo Martini
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 seeking a Full-Stack Account Executive who can credibly sell AI solutions to upper-mid-size and large enterprises. You’ll be responsible for the entire sales cycle—from initial outreach to contract signature—collaborating with our technical team and Customer Success to ensure product-market fit. Being comfortable speaking with C-level executives is crucial. While our primary market is Italy, English (and possibly French/Spanish) skills are strong pluses for our broader expansion.
Key Responsabilities
Identify and qualify leads within enterprise-level organizations (250-1000+ employees).
Conduct high-level product demos and discovery calls, showcasing deep knowledge of AI SaaS solutions.
Navigate complex sales cycles, build strong relationships at the C-suite level, and negotiate deals.
Collaborate closely with Customer Success to ensure smooth pre-sales scoping and post-sales handover.
Accurately forecast pipeline and report on sales metrics.
Help refine our go-to-market strategy, leveraging industry insights and customer feedback.
Required Experience and Skills
Master’s degree (or higher) in Business, Engineering, Computer Science, or a related field.
Proven track record of success selling B2B software (SaaS preferred) to large enterprises.
Comfortable presenting to C-level stakeholders, with strong storytelling and negotiation skills.
Technical acumen to discuss AI-driven solutions (formal tech background is a plus).
Fluency in Italian and strong English communication; French or Spanish is a plus.
Familiarity with CRM and sales methodologies (e.g., SPIN, MEDDIC, or similar).
Plus
Experience in early-stage startup environments.
Knowledge of the Italian enterprise market landscape.
Prior experience with AI or data-driven product sales.
Interview Process
Discovery Interview (30 min): conversation about your background and past experiences.
Mock Discovery Call (45 min): You’ll “sell” an AI SaaS of your choice. We’ll assume we’re the CIO of a mid-sized company in a sector you choose.
Technical Interview (45 min): Discussion focused on AE fundamentals (sales methodologies, pipeline management, CRM best practices).
Behavioral Interview (45 min): Based on SylloTips’ core tenets, following a STAR model.
What We Offer
Employment type: full‑time, permanent
Total Compensation:
€45k - €60k EUR base salary
Uncapped commissions
SylloTips Stock Option Plan
85% Remote Work (from the EU): Expect around ten three-day in-person sessions per year at our Rome offices.
Growth & Collaboration: Work directly with a world-class founding team of AI PhDs and tech veterans.
If interested, send your application to: hiring@syllotips.com
Ps. Feel free to apply even if your rates are higher than that!
