Meet Our Team
Squaremouth’s leaders set the tone and keep the company focused on its mission to make travel insurance comparison simple, transparent, and trustworthy, helping travelers navigate their journeys with confidence.
Rupa Mehta Chief Executive Officer
Rupa is responsible for driving growth, product development, and user experience to reinforce Squaremouth’s position as the leading travel insurance marketplace. Drawing on 20 years in operations, strategy, and corporate development, she leads with a focus on innovation and customer value. She previously held leadership roles at Angi, Groupon, Treehouse Foods, EY, and earned her MBA from the University of Chicago Booth School of Business and a BA in Finance from Michigan State University. View LinkedIn for Rupa Mehta
Jackie Mondelli Chief Marketing Officer
Jacqueline leads marketing at Squaremouth, overseeing digital performance, customer engagement, and brand strategy to strengthen the company’s position as the leading travel insurance marketplace. She uses analytics and customer insights to drive innovative, results-oriented marketing strategies. Before joining Squaremouth, Jacqueline held senior marketing leadership roles at GoHealth, where she focused on multiple insurance verticals, including Medicare, health, life, and small business. She holds a Bachelor of Science in Business Management from Purdue University. View LinkedIn for Jackie Mondelli
Fede Moretti VP of Engineering
Federico leads engineering and technology strategy at Squaremouth, driving the development of innovative, reliable, and scalable solutions that enhance the customer experience. With over 15 years of experience in software development and technology leadership, he brings deep expertise across e-commerce, travel, and tech startups. Federico has held senior roles at Goldbelly, Woopa, ZippySpot, and Globant, and holds a degree in Computer Systems Engineering from the Universidad Nacional del Sur. View LinkedIn for Fede Moretti
Chrissy Valdez Senior Director of Operations
Chrissy leads customer service, training, and quality assurance at Squaremouth, ensuring the company delivers on its mission of transparency and customer-first service. With over 20 years of experience in the travel and assistance industry, she has held senior leadership roles at Aardy, Centurion Travel Assistance, and Jet ICU, and holds an Associate of Science degree from Keiser University – Ft. Lauderdale. View LinkedIn for Chrissy Valdez