Operations Specialist

Operations Specialist

Cruisebound is seeking an Operations Specialist to help shape the future of cruise booking. This is a high-impact, hands-on role for an early-career operator who wants broad ownership across AI, systems, content, and process in customer operations. You will own the tools and automation our support runs on, and you will see the results of your work in the customer experience.

This role is best suited for a systems thinker who is software-savvy, curious about AI, and able to balance rapid execution alongside projects that require deep, careful work. This is an individual contributor role with no direct reports, though you will direct the day-to-day work of our Back Office agents employed by our BPO partners.

Your responsibilities

AI & Systems for Customer Support

• Own the performance of our AI support agents. Configure, test, and continuously improve deflection flows and automated responses across chat, email, and voice.
• Own the content and response library that AI and human agents draw from (articles, macros, canned responses, templates, routing rules). Write, structure, and retire content so answers stay accurate, and improve it based on what the performance data tells you.
• Maintain CRM and support tooling configuration, including intents, workflows, tags, SLA rules, and reporting views.
• Own user provisioning and deprovisioning across our customer operations tools, for employees and BPO agents alike. Keep an accurate record of who has access to what, and revoke access promptly on departure.
• Run QA on customer and agent-facing AI output, and close the gaps yourself through content or configuration changes.
• Own automation reporting. Track deflection, resolution, escalation reasons, and contact volume by intent, and bring leadership a clear point of view on what should change.
• Scout and test new AI and support tools, run the pilot, and make the case for what we should adopt.

Process & Documentation

• Own the documentation and training materials that keep agents current on cruise line policy changes, product releases, and cross-sell updates.
• Document customer operations processes so they are clear, repeatable, and ready to be automated, measured, or handed off cleanly to internal teams and BPO partners.
• Direct the day-to-day work of our BPO Back Office agents on operational processes and product QA. Set queue priorities and quality standards, spot-check output against documented process, and raise quality or adherence issues with the BPO partner.
• Improve procedures for customer communication, booking modifications, transaction-related inquiries and errors, and cruise line escalations, and flag the ones that are not working.
• Partner with customer service, operations, supply, product and engineering to resolve customer operations issues.

Product Collaboration

• Give the product team direct feedback on bugs, feature shortcomings, and new ideas, based on your own usage of the product.
• Investigate booking inconsistencies, errors, and operational issues that come from product shortcomings (such as Pending Bookings), find the pattern behind them, and push for the systemic fix.
• Analyze customer needs, identify problems, and recommend solutions.
• Sample projects you might own
• Rebuild our AI for Agents knowledge base and agent configurations to increase breadth and accuracy and improve agent adoption
• Audit the content library against what customers actually ask, retire what is stale, and write what is missing in an effort to increase AI resolution rates
• Stand up a QA sampling process for AI output, and report findings along with fixes
• Evaluate a new AI support tool end to end: run the pilot, measure it against what we have, and make the recommendation.
• Automate a repetitive Back Office process

The ideal candidate

• Has 1-3 years of experience in customer support, operations, or a systems and tooling role, or equivalent practical experience
• Is an early adopter: tries new tools on their own, has opinions about the ones they use, and pays attention to where AI is heading for customer support
• Has hands-on experience writing and iterating on prompts, and understands how wording, structure, examples, and context change the output. Tests a prompt change and reads the result rather than guessing at it
• Thinks in systems: comfortable with workflows, rules, tags, and intents, and finds the upstream cause rather than fixing the same thing twice
• Is curious, proactive, and self-directed, and does not wait to be told what to do
• Balances attention to detail with an MVP mindset and bias toward action
• Nice to have: admin experience with a modern CRM or support platform (Kustomer, Intercom, Zendesk, Salesforce or similar), comfort with business intelligence tooling

Compensation and benefits

• The compensation package for this position comprises: (1) a base salary ranging from $60,000 to $70,000 depending on the candidate’s experience, knowledge, and skills, and (2) an employee stock option grant. In addition, we also offer our employees a comprehensive range of benefits including but not limited to:
• $1,000 annual cruise credit to use on Cruisebound.com and additional employee rebates
• Excellent health care insurance (medical, dental, vision, long-term disability, etc.)
• Generous personal paid time off (PTO) allowance beginning with 20 days in the first year, plus 2 additional days per year of tenure (up to 30 days total)
• 4 company-wide holidays (first Friday of each quarter) and 12 public holidays observed
• $100/month communication credit intended for cell phone and Wi-Fi expenses

About Cruisebound
Our mission is to help cruisers book their dream vacation by creating the best online booking experience for cruises.

We are customer centric: we focus on finding the fastest and most intuitive way to solve customer pain points. We are decisive: we don’t let perfect be the enemy of good. We are data driven: support every decision with data. We are one crew: we win and lose together, we are not afraid to make mistakes and learn from them.
Our founding team previously built and scaled Rocket Travel, a travel startup, to $900M in revenue. Rocket is now part of Booking Holdings, the world leader in travel. We are a diverse team from around the globe who have learned about the travel industry at places like Booking.com, United Airlines, McKinsey, BCG, Stanford, and MIT.