SMB Sales Executive

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🕒 May 27

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Triptease

WebsiteLinkedInAll Job Openings

51 - 200 employees

Hospitality • Software • Marketing

Triptease is a platform dedicated to transforming hotel website experiences to drive direct bookings and optimize pricing strategies. The company offers a range of tools, including metasearch integration, price matching, personalized messaging, and AI-driven chat, all aimed at improving direct sales and customer engagement. Triptease focuses on providing hotels with dynamic pricing, effective marketing, and data-driven automation solutions to outperform Online Travel Agencies (OTAs). Their solutions are designed to enhance revenue through CRM integration and personalized marketing strategies, ensuring that hotels can maintain competitive pricing and attract the right guests. With a mission to support the Direct Booking Movement, Triptease offers seamless integration with numerous booking engines and provides extensive resources such as webinars, events, and customer stories to help hoteliers increase direct bookings and improve their revenue management practices.

📋 Description

• Build strong relationships with independent hotels and groups through calls, emails, and compelling demos. • Become a voice for Triptease in the NORAM market — outbound prospecting and brand-building. • Own your territory: Create and execute smart engagement strategies and cadences. • Leverage tools (like Salesforce, Outreach, Apollo, Clay) and experiment with AI-driven outreach to personalize and scale faster. • Pitch, negotiate and close — tailoring solutions that help hotels win. • Craft strategic proposals based on performance data, marketing pain points, and competitive insights.

🎯 Requirements

• Have 1–3 years of outbound sales experience (ideally SaaS, ad-tech, or travel tech). • Are a natural relationship builder, but love to close just as much. • Thrive under pressure, bounce back fast, and love learning new techniques. • Have experimented with automation tools, personalized outreach, or even AI in sales workflows (or are eager to start). • Want to work autonomously, but love being part of a hungry, collaborative team. • Bonus Points For: • Exposure to hotel tech, travel tech or eCommerce • Knowledge of sales methodologies (SPIN, Challenger, Sandler) • Being a tech tinkerer: You’re already trying out AI tools or sales automation hacks

🏖️ Benefits

• Uncapped commission + stock options • 21 days PTO (increases after 1 year) • Work from anywhere (within ±3h of ET) + work abroad for 4 weeks/year • Pre-tax commuter benefits • Health & dental coverage • 401(k) with 3% match • $68 monthly wellness budget (Ben) • $325 annual learning budget • Enhanced maternity & paternity • Flex for childcare & life events • Volunteering day + discovery days + social retreats