SMB Sales Executive

Summary

Join Triptease, a company revolutionizing the hotel industry with AI-powered tools, and help hoteliers increase direct bookings and improve margins. This remote sales position offers a unique opportunity to work in a fast-paced, dynamic environment, utilizing cutting-edge technology to drive sales. As a sales professional, you will build relationships with hotels, execute strategic engagement plans, leverage AI-driven outreach, and close deals. The role requires 1-3 years of outbound sales experience, ideally in SaaS, ad-tech, or travel tech. Competitive compensation includes an uncapped commission, stock options, and comprehensive benefits.

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

Responsibilities

• 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

Preferred Qualifications

• 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
• 15 days PTO (increases after 2 years)
• 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