SMB Sales Executive

Triptease
$65,000 - $95,000Remote

About The Position

Triptease is on a mission to level the playing field for hotels. In a world dominated by OTAs (Online Travel Agents), we’re giving power back to hoteliers — helping them drive more direct bookings, improve margins, and own their guest relationships. Our platform combines proprietary hotel data, AI-driven marketing tools, and advanced pricing intelligence to give hoteliers an edge. With over £1 billion in direct revenue driven for clients annually and a global presence - this is your chance to be part of something big. This is not your average sales gig. We’re looking for ambitious, high-energy sales professionals who want to scale with a company that’s changing the game in travel tech. If you’re someone who thrives in fast-paced environments, loves owning your number and your day, gets fired up by new tools like AI, automation, and data-powered selling, and wants to sell products with purpose and impact, then this role is for you.

Requirements

  • 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.

Nice To Haves

  • 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

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.

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
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