About Delos Insurance SolutionsDelos is a technology-forward insurance company focused on the Excess & Surplus (E&S) market. We’re reimagining specialty insurance by leveraging automation and data to underwrite complex risks efficiently. As we scale into additional states, we are strengthening our compliance infrastructure to ensure operational excellence and continuous regulatory alignment.Position OverviewThe Systems Administrator is a fully hands-on role responsible for managing the performance, reliability, and integration of Delos’ core business systems. The ideal candidate will have deep functional knowledge of HubSpot CRM, Zoom Phone, and Guidewire InsuranceNow, and will be able to recreate, redesign, and optimize workflows to better support our current and future operational needs. This role blends tactical internal IT support with proactive system configuration and automation work - ensuring our tools function seamlessly together, strengthening data integrity, and enabling scalable growth. This is a highly cross-functional position supporting teams across the business in a fast-paced and evolving environment.Key ResponsibilitiesServe as the primary hands-on administrator for HubSpot CRM, Zoom Phone, Google Workspace, Guidewire InsuranceNow, and Delos proprietary portalsEvaluate current workflows and rebuild integrations and automations to improve operational efficiency and user experienceProvide internal IT support including onboarding/offboarding, device management, troubleshooting, and endpoint securityManage access controls, user permissions, and audit readiness in support of compliance requirementsCollaborate with external vendors and IT contractors to deliver enhancements and maintain high system uptimeTroubleshoot system issues, conduct root-cause analysis, and implement solutions to prevent recurrenceMaintain SOPs, knowledge base content, and change documentation for system enhancementsMonitor and report on system performance, utilization, and scalability risksContribute to technology roadmap planning and execution, including feature evaluations and adoptionProtect systems and data through strong cybersecurity and business continuity practicesQualifications3+ years in systems administration, IT operations, or similar hands-on technical roleDirect administration experience with HubSpot CRM and/or Zoom Phone required; Guidewire platform experience strongly preferredWorking knowledge of workflow automation, APIs, or iPaaS tools (e.g., Zapier, Workato, Boomi)Experience with identity and access management, device management platforms, and modern security controlsStrong analytical, troubleshooting, and documentation skillsAbility to collaborate effectively with both technical and non-technical stakeholdersExperience in a regulated environment (e.g., SOC2) or insurance industry experience is a plusWhat You Will BringA builder’s mindset - comfortable digging in and creating solutions hands-onStrong ownership of outcomes, accountability, and continuous improvementClear, confident communication in fast-moving and cross-functional settingsCompensation and BenefitsCompetitive salary plus equity stock optionsFlexibility to work from anywhere in the United StatesUnlimited PTO, including sick leave and company holidaysComprehensive medical, dental, vision, and life insurance (25% paid by employee, 75% covered by Delos including dependents)401(k) retirement savings planProfessional development opportunities and tuition assistance
