Customer Success Executive, SMB (Customer Success Manager)

Triptease; United States; On-site; USD 90,000 - 120,000; Full time

Job summary

Triptease is seeking a strategic, commercially-minded Customer Success Executive to join its Global SMB team. You will own a book of small and medium-sized hotel clients across AMERS, guiding them from trial through to long-term partnership.

You’ll drive adoption, hit commercial goals (direct bookings, conversion, revenue), and scale your impact with AI tools. Collaborate with Product, Marketing and Sales to convert value into retention and expansion.

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.
• U.S. Customer Experience: Previous experience working directly with U.S.-based customers is required.

Responsibilities

• 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.
• Be Their Strategic Partner — Act as the trusted advisor for your book of SMB hotels. Understand each client's commercial goals and build a point of view on how Triptease gets them there.
• Drive Retention and Renewals — Deliver high retention across the SMB base by demonstrating measurable value. Identify churn risk early and work with Product to clear blockers.
• Grow the Book — Spot upsell and cross-sell opportunities across your accounts. Partner with Sales to land expansion deals and grow net revenue retention.
• Scale Yourself with AI — Use AI tools to multiply your impact, summarizing performance and drafting communications.
• Work Across Teams — Partner with Product, Marketing, and Sales to feed back customer insight and launch one-to-many campaigns.
• Keep the Data Trustworthy — Maintain accurate records across Vitally, Salesforce, and other CS systems.

Skills

Customer Success

Account Management

B2B SaaS

US Customer Experience

AI Tools

BI Tools

Tools

Salesforce

Vitally

Looker

JIRA

Linear

Job 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.

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.

• 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

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.