Senior IT Support Lead — Remote & On-Call

Kingstone Insurance Company; New York (NY); Hybrid; USD 80,000 - 95,000; Full time

Benefits offered by this job

Health benefits

Life insurance

Disability insurance

401(k) with match

Parental leave

Paid time off

Job summary

Kingstone Insurance Company is seeking a Senior Support Specialist for a fully remote role with occasional visits to the New York office as needed. You will own escalations, validate support execution, and drive audit readiness across IT support functions.

The position requires 5+ years in senior IT support in a corporate setting, experience with Jira, and strong troubleshooting and communication skills. Expect on-call rotation and close collaboration with IT and business teams.

Qualifications

• Bachelor's degree or equivalent combination of education and relevant work experience.
• 5+ years of experience in senior IT support or service delivery within a corporate environment.
• Experience working with ticketing systems (Jira or equivalent).
• Demonstrated ability to handle escalations and complex support scenarios.
• Experience supporting SaaS applications and enterprise user environments.
• Deep understanding of audit, compliance, and regulatory processes.
• Experience in a regulated industry such as insurance, finance, or banking.
• Experience mentoring or serving as a senior point of escalation for other support staff.
• Familiarity with Microsoft enterprise environments (O365, Intune, device management).
• Strong troubleshooting and critical thinking skills.
• Excellent verbal and written communication skills.
• Ability to identify process gaps.
• Strong organizational skills and attention to detail.
• Demonstration of strong bias toward action, ownership, and proactive follow-through.
• Comfort operating in ambiguity and high-priority situations.

Responsibilities

• Act as a senior escalation point for Support Desk team members, handling complex or high impact support issues.
• Own incident coordination and follow-through for escalated issues, ensuring appropriate communication, prioritization, and resolution.
• Determine when issues should be escalated to Project Management or with vendors and coordinate accordingly. Ensure all requirements for escalation are met.
• Maintain strong situational awareness of open incidents, risks, and service impacts.
• Provide guidance and mentorship to Support Desk staff on troubleshooting techniques, escalation judgment, and customer communication.
• Maintain a strong working knowledge of Kingstone systems, applications, and support processes.
• Participate in onboarding and offboarding activities, ensuring the quality and completeness of support execution. (Onboard/Offboard QA, Onboard Meetings, Laptop QA)
• Identify recurring issues or process gaps and recommend improvements.
• Support audit and access review activities by validating documentation, access accuracy, and adherence to defined processes.
• Partner and collaborate with IT and business teams on complex or systemic issues.
• Drive root cause analysis for recurring or high-impact incidents and ensure preventative actions are defined and tracked.
• Participate in On-Call rotation

Skills

Senior escalation

Escalation management

SaaS support

Microsoft 365

Communication

Education

Bachelor's degree

Tools

Jira

Job description

Kingstone Insurance Company is seeking a Senior Support Specialist for a fully remote role with occasional visits to the New York office as needed. You will own escalations, validate support execution, and drive audit readiness across IT support functions.

The position requires 5+ years in senior IT support in a corporate setting, experience with Jira, and strong troubleshooting and communication skills. Expect on-call rotation and close collaboration with IT and business teams.