Customer Success Executive, SMB

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.

What You'll Do

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. You'll 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. You'll 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. You'll 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.

Requirements

• The "Automate Everything" Mindset: You are obsessed with efficiency and hate doing the same manual task twice. You approach work with this logic:

  At SMB scale this is the whole job. With a large book of accounts, the CSE who builds a reusable performance template or an automated risk trigger will always beat the one working account by account. We give you AI tools and the freedom to use them - we expect you to.

• First time: You solve it and wonder if it will happen again.
• Second time: You build a template or tool to automate the majority of the task.
• Third time: You actively work to automate the process from start to finish so you never have to do it manually again.
• Commercial Instinct: You think about customer success in terms of business outcomes - revenue, conversion, retention - not just usage or sentiment. You're comfortable reading performance data and translating it into a conversation a GM or Revenue Manager actually cares about.
• Experience: 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.
• U.S. Customer Experience: Previous experience working directly with U.S.-based customers is required. You understand the communication styles, service expectations, and commercial dynamics of supporting customers in the U.S. market.
• Language: Full professional fluency in English, both written and spoken, is required. You'll communicate daily with U.S.-based customers and colleagues, including leading client meetings, delivering presentations, and discussing nuanced commercial and technical topics.
• AI Adopter: You're already using AI tools in your day-to-day work and you're curious about what's next. You see AI as a force multiplier, not a threat.
• Tooling: Comfort working with modern CS and BI tools - Salesforce, Vitally, Looker, or equivalents. You don't need to be a data analyst, but you should know your way around a dashboard.
• Communication: Strong written and verbal communication. You can run a video training session, write a tight renewal email, and flag risk to leadership without burying the lede.
• Adaptability: You thrive in a fast-paced environment where product, process, and priorities evolve.

⭐ Nice-to-Haves

• U.S. Hospitality Experience: Experience supporting U.S.-based customers in hospitality, travel technology, hotel technology, or a related industry is a strong plus.
• Hospitality Knowledge: 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

We're a well looked after bunch, with excellent benefits (these vary by location):

• 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.