[Hiring] Customer Success Executive @Triptease

Role Description

We're looking for a strategic, commercially-minded Customer Success Executive to join our Global SMB team. You'll own a book of small and medium-sized hotel clients — primarily across AMERS, but with exposure to customers in other regions — guiding them from trial through to long-term partnership. This isn't a ticket-taking role. You'll be responsible for helping hoteliers hit the commercial goals that matter to them — direct bookings, conversion, revenue — and for spotting the moments where Triptease can do more for them. You'll run at scale, which means automation and AI aren't optional extras; they're how the job gets done well.

• Own the Trial: Take ownership of the customer experience through the critical 3-month trial period. Set clear success criteria with each client, drive adoption and performance against them, and convert trials into full-term contracts. Continuously refine the onboarding playbook so new hotels see value faster, with less manual effort from you.
• Be Their Strategic Partner: Act as the trusted advisor for your book of SMB hotels. Understand each client's commercial goals (direct booking revenue, conversion rate, parity position, channel mix) and build a point of view on how Triptease gets them there. Lead performance check-ins, business reviews, and training sessions that tie product usage to business outcomes.
• Drive Retention and Renewals: Deliver high retention across the SMB base by demonstrating measurable value. Identify churn risk early, handle objections head-on, and work with Product and internal stakeholders to clear blockers before they become exits.
• Grow the Book: Spot upsell and cross-sell opportunities across your accounts: additional products, expanded ad spend, new properties. Partner with Sales to land expansion deals and grow net revenue retention across the segment.
• Scale Yourself with AI: Apply the "Automate Everything" mindset to your own work and to the SMB playbook. Use AI tools to multiply your impact — summarizing performance, drafting communications, triaging at-risk accounts — so you spend more time on the strategic work only a human can do.
• Work Across Teams: Partner with Product, Marketing, and Sales to feed back customer insight, shape the SMB experience, and launch one-to-many campaigns. Report on client performance, trial conversion, retention, and expansion to senior management.
• Keep the Data Trustworthy: Maintain accurate, current records across Vitally, Salesforce, and our other CS systems so the wider business can rely on your numbers.

Qualifications

• 2+ years in Customer Success, Account Management, or a similar client-facing role, ideally in B2B SaaS.
• Experience managing SMB books at scale — high account count, recurring automated touchpoints — is a strong plus.
• Previous experience working directly with U.S.-based customers is required.
• Full professional fluency in English, both written and spoken, is required.
• Comfort working with modern CS and BI tools — Salesforce, Vitally, Looker, or equivalents.
• Strong written and verbal communication skills.
• Ability to thrive in a fast-paced environment where product, process, and priorities evolve.

Requirements

• Experience supporting U.S.-based customers in hospitality, travel technology, hotel technology, or a related industry is a strong plus.
• Familiarity with hotel operations, digital marketing, revenue management, distribution, or direct-booking strategies.
• Familiarity with issue-tracking tools like Linear or JIRA.
• A track record of building automations, templates, or small tools to streamline your own work.

Benefits

• A competitive salary and bonus plan.
• Regular career development reviews — we reward great work.
• Fun events for Tripteasers.
• Something important to you that's not on this list? Talk to us.