Vice President Enterprise Sales

AI-Powered Travel Subscriptions | Rome, Italy

We’re building a breakthrough AI-driven travel optimization and subscription platform that is reshaping how large enterprises and SMEs manage and buy corporate travel.

Backed by 20+ years of MIT-rooted R&D and deep aviation expertise, we are now seeking a world-class Vice President – Enterprise Sales to scale this business across Italy and Europe , with the ambition to build a multi-billion-dollar category leader .

Optiontown is an innovative Vertical Agentic AI company built on more than two decades of MIT-origin research , deep optimization science, and a portfolio of 20+ issued patents .

Our platform integrates:

• Agentic automation
• Deep personalization engines
• Advanced subscription-optimization frameworks

Together, these power the next generation of high-flexibility, high-value subscription products for global enterprises.

We are now applying this proven technical foundation to transform how large enterprises and SMEs manage corporate travel budgets , delivering fixed budgets, optimization, and automation at scale.

A proven enterprise sales veteran with 20+ years of experience selling multi-million-dollar solutions end-to-end to C-level executives at Fortune 1000 companies , based in or doing business in Italy .

✔ Consistent success closing $MM+ enterprise deals , preferably with corporate travel buyers

✔ Strong preference for experience selling corporate travel, travel contracts, or enterprise SaaS

✔ Deep mastery of long-cycle enterprise sales

    (hunting → pitching → negotiation → closing → expansion)

✔ Experience building and leading high-performing enterprise sales teams

✔ Bachelor’s degree from a top European university ; MBA preferred

✔ Enjoys travel, in-person client engagement, wining & dining, and CXO relationship building

✔ Highly entrepreneurial, resourceful, and comfortable building from the ground up

Preference: Candidates who have lived and worked in Rome or Milan and have closed multi-million-dollar enterprise deals with Italian corporations .

• Build and scale the enterprise sales engine for Italy and Europe

• Win major Fortune 100 / Fortune 1000 corporate travel contracts

• Shape GTM strategy, partnerships, pricing models, and revenue roadmap

• Operate as a true entrepreneurial sales leader with significant equity and full autonomy

If you’re a top-performing enterprise sales leader ready to transform corporate travel and build something enduring, let’s talk.

• Please message your resume along with a short cover note explaining how you meet the role criteria.