Sr. Systems Administrator

About Delos Insurance Solutions

Delos 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 Overview
The 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 Responsibilities

• Serve as the primary hands-on administrator for HubSpot CRM, Zoom Phone, Google Workspace, Guidewire InsuranceNow, and Delos proprietary portals
• Evaluate current workflows and rebuild integrations and automations to improve operational efficiency and user experience
• Provide internal IT support including onboarding/offboarding, device management, troubleshooting, and endpoint security
• Manage access controls, user permissions, and audit readiness in support of compliance requirements
• Collaborate with external vendors and IT contractors to deliver enhancements and maintain high system uptime
• Troubleshoot system issues, conduct root-cause analysis, and implement solutions to prevent recurrence
• Maintain SOPs, knowledge base content, and change documentation for system enhancements
• Monitor and report on system performance, utilization, and scalability risks
• Contribute to technology roadmap planning and execution, including feature evaluations and adoption
• Protect systems and data through strong cybersecurity and business continuity practices

Qualifications

• 3+ years in systems administration, IT operations, or similar hands-on technical role
• Direct administration experience with HubSpot CRM and/or Zoom Phone required; Guidewire platform experience strongly preferred
• Working 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 controls
• Strong analytical, troubleshooting, and documentation skills
• Ability to collaborate effectively with both technical and non-technical stakeholders
• Experience in a regulated environment (e.g., SOC2) or insurance industry experience is a plus

What You Will Bring

• A builder’s mindset - comfortable digging in and creating solutions hands-on
• Strong ownership of outcomes, accountability, and continuous improvement
• Clear, confident communication in fast-moving and cross-functional settings

Compensation and Benefits

• Competitive salary plus equity stock options
• Flexibility to work from anywhere in the United States
• Unlimited PTO, including sick leave and company holidays
• Comprehensive medical, dental, vision, and life insurance (25% paid by employee, 75% covered by Delos including dependents)
• 401(k) retirement savings plan
• Professional development opportunities and tuition assistance