Customer Technical Support Specialist
About the Company
Aspire Software operates and manages wholly owned software companies, providing mission-critical solutions across multiple verticals. By implementing industry best practices, Aspire delivers a time sensitive integration process, and the operation of a decentralized model has allowed it to become a hub for creating rapid growth by reinvesting in its portfolio.
Role Overview
As a technical customer support specialist, you are often the first person a hotel contacts when something in its property management system is not working—sometimes during check-in and with guests waiting.
You will help customers use our software effectively, answer "how-to" questions, diagnose technical problems, and resolve issues across a broad range of hospitality products and integrations. This includes explaining workflows, guiding users through configuration and operational tasks, reproducing reported problems, and determining whether an issue is related to data, configuration, permissions, an integration, or a software defect. You will resolve as much as possible during the initial interaction. When escalation is required, you will document the issue with enough evidence and context that the next person can continue the investigation without starting over.
Tickets are initially triaged and tagged through AI-assisted workflows. You will assess that triage, correct it when necessary, review drafted responses, and take over the conversation whenever a customer needs direct assistance from a person.
What You Will Do
Work the shared support queue
Pull tickets from the team’s shared queue, prioritize your workload based on severity, customer impact, and ticket age, and take ownership of each issue through resolution. The team works toward shared service and open-ticket goals rather than relying only on individually assigned inboxes.
Support customers across every channel
Provide support through phone, email, and chat. Adjust your communication style to the situation, whether you are answering a straightforward software question or leading a live troubleshooting call with a hotel experiencing an urgent operational issue.
Answer product and workflow questions
Help customers understand how to use the software in their day-to-day hotel operations. This includes explaining features, walking users through processes, helping with configuration, and identifying when a "how-to" question is actually the result of incorrect setup, missing permissions, or unexpected system behavior.
Work with AI-assisted support tools
Review AI-generated classifications and drafted responses before relying on them as our answer. Correct intent, priority, sentiment, language, and product classifications when necessary, and suppress automated responses when they would be inappropriate, including security, legal, or previously escalated matters.
AI output is a starting point. You remain accountable for the accuracy of the response and for confirming that the customer’s issue has been resolved.
Diagnose issues across our product portfolio
Support roommaster Cloud, roommaster Anywhere, our browser-based PMS, Booking Engine and Channel Manager, roommaster Payments, Caretaker/Eventory and many more.
Identifying the correct product, environment, database region, and affected workflow is often the first step in the diagnostic process.
Troubleshoot integrations
Investigate issues involving data moving between connected systems, such as:
Availability not reaching an online travel agency
Reservations not arriving in the PMS
Rates or restrictions not updating
Transactions missing from reports
Third-party systems returning incomplete or unexpected data
Use logs, audit trails, request and response data, and the behavior of both systems to determine where the handoff failed.
Support card payments and terminals
Assist with payment-terminal setup and connectivity, batch and settlement questions, refund, duplicate charges, tokenization, and processor-side issues. Understand what can be addressed within roommaster and when the issue must be escalated to another internal team.
Support distribution and OTA connectivity
Troubleshoot room and rate mapping, availability and restriction updates, and connections with platforms such as Booking.com, Expedia, Agoda, and Airbnb.
Recognize the operational impact of distribution issues. For example, a stalled availability update that could cause a hotel to oversell rooms requires a different response than a routine mapping question.
Maintain accurate support records
Ensure each ticket contains the correct:
Ticket form and classification
Customer organization and contact
Product and product-automation fields
Priority and severity
Problem-versus-question classification
Troubleshooting notes and supporting evidence
Contacts must be associated with the correct organization, and all required information must be completed before a ticket is resolved.
Reduce repeat contact
When the same question or issue appears repeatedly, help turn the solution into a reusable macro, internal procedure, Help Center article, training opportunity, or product improvement request. Helping customers find answers more easily and preventing repeat issues are core parts of the role.
Participate in our global support schedule
Our customers operate across North America, EMEA, and APAC. Support follows a global, follow-the-sun model, and this role participates in a shift rotation that includes weekend coverage.
Requirements
At least one year of experience in technical support, application support, software support, or a comparable customer-facing technical role
A structured diagnostic approach: reproduce the issue, isolate variables, form and test a hypothesis, and escalate with evidence
Ability to distinguish among a product question, data issue, configuration problem, permissions issue, integration failure, and software defect
Comfort using browser developer tools, including reviewing console errors and inspecting failed network requests
Working knowledge of APIs and integrations, including HTTP status codes, request and response payloads, and webhooks
Ability to reconstruct events using logs, audit trails, transaction histories, and customer conversations
Strong written English and the ability to produce clear, accurate responses suitable for customers, hotel management, processors, vendors, and other stakeholders
Clear and confident spoken English, including the ability to lead a live call with a customer experiencing a stressful operational issue
Ability to manage and prioritize your workload without needing to be given a daily task list
Strong ownership and follow-through, including confirming that the customer’s issue has been resolved
Availability to participate in a shift rotation covering a 24/7 support structure
Beneficial Experience
Hotel front-desk, reservations, accounting, or back-office experience
Experience with card payments or payment terminals, including Adyen, or another hotel or retail payment provider
Experience with channel managers, booking engines, or OTA extranets
Experience with Zendesk or a comparable ticketing platform
SQL knowledge or experience building reports from a relational database
Basic networking knowledge
Ability to use AI-assisted tools effectively while critically evaluating their output for accuracy, relevance, tone, security, and appropriateness
Experience supporting SaaS products or connected software platforms
Hotel experience is valuable, but it is not required. We can teach hospitality operations to someone who already has strong technical troubleshooting and customer communication skills.
What We Will Teach You
How a hotel operates
You will learn the daily hotel cycle, from reservations and arrivals through check-in, folio management, and night audit. You will also learn hospitality terminology such as rate plans, availability and restrictions, no-shows, walk-ins, room moves, and overbooking.
Understanding hotel operations is essential to determining the true urgency and impact of an issue.
Why certain issues are emergencies
A stalled availability update is not simply a data-sync problem—it may place a hotel at immediate risk of selling rooms it does not have.
You will learn which issues create operational or financial risk, how quickly that risk develops, and how to respond appropriately.
Our products and environments
You will learn how properties are configured across our products, regions, integrations, and database environments, as well as how to identify the systems involved in a reported issue.
Payments from end to end
You will learn how payment terminals, tokenization, authorization, batching, settlement, refunds, and payment processors interact—and, importantly, what data and processes support must never access or modify.
Distribution and connectivity
You will learn how room and rate mapping works, how availability and restriction updates move between systems, and how major OTA extranets behave.
Escalation and incident management
You will learn our escalation process, severity criteria, duplicate-ticket linking, documentation requirements, and communication expectations during active incidents.
How the Team Works
Our workload follows hotel operations
Support volume is heaviest on weekdays and typically peaks on Mondays as issues from the weekend are reported or followed up. A typical weekday generates approximately 105 support tickets, while a weekend day generally generates 38–40. These tickets are shared across the team.
AI assists the team
AI helps classify, route, and prioritize tickets and can draft suggested responses. Support specialists remain responsible for validating its output, applying judgment, and ensuring that the customer receives an accurate and complete resolution.
We work as one support team
The team shares responsibility for the queue and overall customer experience. Collaboration is expected: team members help one another investigate issues, share product knowledge, and move difficult tickets toward resolution.
Success is not measured by individual ticket volume alone.
Performance is balanced
Performance is evaluated across several areas, including:
Resolution quality and accuracy
Responsiveness
Customer satisfaction
Ticket ownership and follow-through
Documentation and ticket hygiene
Appropriate prioritization and escalation
Contribution to the performance and knowledge of the wider team
Ticket volume is considered in context and does not, by itself, determine performance.