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 — 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 dynami