Senior Technical Support Specialist

We are looking for a Senior Technical Support Specialist to join a growing B2B SaaS organization and take ownership of complex technical issues from initial escalation through resolution.This is a hands-on role for someone who enjoys troubleshooting, investigating system behavior, identifying root causes, and working closely with Engineering and Product to resolve issues effectively. The ideal candidate can take an unclear customer-reported problem and turn it into a structured technical investigation with clear findings and actionable next steps.What You’ll DoTake ownership of complex technical issues and drive them through investigation, resolution, and follow-up.Analyze reported problems to determine whether they are related to product functionality, configuration, user workflows, data, suppliers, or integrations.Reproduce issues and document expected vs. actual behavior, reproduction steps, affected users, and business impact.Investigate system behavior using internal tools, system records, historical tickets, session-replay tools, and other technical resources.Review issue severity and prioritize investigations based on customer impact, operational risk, urgency, and available workarounds.Create detailed and actionable Jira tickets for Engineering, ensuring all relevant evidence and technical context is included.Work closely with Engineering and Product teams on bugs, known issues, releases, and customer-impacting technical problems.Develop practical and safe workarounds that allow customers to continue operating while permanent solutions are being developed.Translate technical findings into clear, customer-friendly guidance for Customer Care and other non-technical teams.Validate fixes following releases and confirm that issues have been fully resolved before closing them.Support and coach Customer Care teams on troubleshooting, issue classification, evidence gathering, and escalation practices.Help develop troubleshooting guides, investigation checklists, known-issue documentation, and technical support processes.Identify recurring issues and provide structured feedback that can improve the product and reduce repeat support cases.Contribute to building and scaling the organization’s Technical Support function, including processes, documentation, tools, and workflows.What We’re Looking For5+ years of experience in Technical Support, Product Support, Support Engineering, or a similar technical position within a B2B SaaS environment.Strong experience troubleshooting and investigating complex software issues rather than simply routing tickets.Ability to identify root causes and distinguish between symptoms, configuration issues, workflow problems, data inconsistencies, bugs, and integration-related issues.Experience reproducing technical issues and creating detailed Jira tickets for Engineering.Working knowledge of web applications, APIs, integrations, permissions, system data, and data flows.Experience using technical investigation tools such as browser developer tools, session replay, internal admin tools, system records, or similar platforms.Strong written and verbal communication skills, with the ability to explain technical findings to both technical and non-technical audiences.Excellent organization and prioritization skills with the ability to manage multiple investigations simultaneously.Comfortable collaborating with Customer Care, Product, Engineering, and Operations.Customer-focused mindset with strong ownership and follow-through.Comfortable working in a fast-growing environment where processes and best practices are still being developed.Nice to HaveExperience with any of the following would be a plus:Hospitality or hotel technologyProcurement, purchasing, or Procure-to-Pay (P2P)Accounts Payable, inventory, or supplier management platformsERP or accounting system integrationsJira, Intercom, LogRocket, or similar toolsREST APIs, webhooks, SFTP, authentication, or file-based integrationsAI-assisted customer support or support automationBuilding or scaling a Technical Support functionKnowledge management, troubleshooting playbooks, or structured support workflowsWhat Success Looks LikeThe right person will be someone who takes ownership, investigates before making assumptions, communicates clearly, and stays with a problem until it is truly resolved. You should enjoy understanding how systems work, solving ambiguous technical problems, and helping create better processes as the Technical Support function grows.