SMB Sales Executive

💼 Location: Remote (U.S.-based)

💰 Salary: Up to $65,000 base + $25,000 - $30,000 OTE (uncapped commission)

🧠 Start-up energy. Global impact. AI-powered future.

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

✅ Wants to sell products with purpose and impact...

...Then read on.

• 💬 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.

• 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.

• 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

• 💸 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

This is your chance to get in early on Triptease’s next stage of growth in North America. You’ll have space to experiment, freedom to win your way, and support from a global team of sales leaders, marketers, product experts and technologists.

Triptease isn’t just another SaaS company — we’re building a smarter, more independent future for thousands of hotels and millions of travellers.

Come build with us.

Triptease is proud to be an equal opportunity employer. We believe diverse teams drive better outcomes and create better products. We welcome applicants from all backgrounds.

We do not require any support from external recruitment agencies. Thank you.

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