IT Support Specialist I or II

Chesapeake Employers' Insurance Company • Towson, MD

7d • $25 - $43 • Hybrid

About The Position

Chesapeake Employers’ Insurance Company is a purpose-driven organization dedicated to improving the lives and livelihoods of our policyholders, injured workers, team members, and the community. As a leading workers' compensation specialty insurer in the mid-Atlantic region, we take pride in being a force for good. Our 350 team members are committed to making a positive impact every day in the lives of all our stakeholders. Join our motivated, professional team as we foster a culture of values, teamwork, innovation, and collaboration. Established in 1914, Chesapeake Employers Insurance, headquartered in Towson, Maryland, has over a century of experience, a strong financial foundation, and an "A" rating from AM Best.

IT Support Specialist I
Position Summary
Provides first-tier technical support to internal teammates and external users by resolving basic technology issues, managing service desk requests, and supporting end-user technology needs. This role serves as the primary point of contact for help desk inquiries and supports daily IT operations.

IT Support Specialist II
Position Summary
This position provides second tier help desk support to employees and Help Desk staff in a Windows / Office environment; while also participating in various IT projects. This position also services outside policyholders, agents, and external customers and equipment vendors.

Requirements

• Basic knowledge of Windows operating systems, Microsoft Office applications, and end-user hardware.
• Strong customer service and communication skills.
• Ability to document procedures and solutions clearly.
• Strong attention to detail and problem-solving skills.
• Ability to prioritize tasks in a help desk environment.
• Proficiency with service desk and ticketing systems.
• Associate degree, technical diploma, or equivalent experience.
• Zero (0) to two (2) years of experience providing help desk or IT support.
• Effectively utilizes technologies and tools, including Microsoft 365 and role-specific platforms, to support productivity and efficient work practices.
• Bachelor’s Degree in an IT related field.
• 2-4+ years’ experience providing help desk support in a medium to large organization.
• 6+ years of relevant help desk experience required without a Bachelor’s Degree.
• Experience with help desk processes, software, and procedures in a medium to large organization.
• Troubleshooting ability with telecommunication, hardware, software and data network.
• Working knowledge of computer technology industry trends and technology advancements.
• Familiarity with Microsoft office and operating systems, group policy, and account management.
• Familiarity with security products such as threat detection and anti-virus.
• Strong customer service orientation and interpersonal skills with users at all levels within the organization.
• Strong interpersonal and oral/written communication skills.
• Proven analytical, multitasking, and problem-solving abilities.
• Experience working independently and in a collaborative team-oriented environment.
• Ability to effectively prioritize and execute tasks.
• Ability to conform to shifting priorities, demands and timelines.
• Initiative to take on new tasks and resolve problems independently.

Nice To Haves

• Relevant IT certifications such as A+, Network+, or Microsoft certifications.
• Microsoft Certified Professional or greater preferred. May substitute other technical certifications that pertain to related Information Technology.
• Bilingual skills preferred.

Responsibilities

• Provides first-tier technical support to internal teammates and external users by receiving, documenting, prioritizing, and resolving help desk incidents and service requests.
• Serves as the initial point of contact for technology-related issues including workstation setup, hardware, software, and account access support.
• Escalates unresolved or complex technical issues to higher-tier support teams in accordance with established procedures.
• Creates and maintains accurate service desk tickets to support timely resolution and reporting.
• Supports external policyholders, agents, vendors, and third-party administrators with basic system access guidance.
• Performs basic troubleshooting related to operating systems, printers, network connectivity, and standard business applications.
• Maintains inventory of end-user hardware assets and ensures documentation is current in the service desk and CMDB.
• Supports deployment, imaging, setup, and replacement of end-user devices such as laptops and peripherals.
• Develops and maintains written procedures and documentation for common support tasks.
• Provides basic end-user training and support during onboarding and technology rollouts.
• Participates as a team member in IT projects including deployments, upgrades, and infrastructure initiatives.
• Maintains compliance with company privacy, data security, and information protection policies.
• Receives and prioritizes work, project-oriented tasks, and service desk requests of varying severity, documenting issues via service desk and document repository, and effectively managing and resolving all issues within accepted service levels and approvals. Initiates corrective action to stay on schedule.
• Serves as the second line of technical support for employees.
• Assists in providing Level I Support when request volumes are high and performs post-resolution follow ups with Level I Technicians as required.
• Installs/upgrades/maintains/supports various computer hardware and software applications.
• Assists users, troubleshoots second tier hardware, software, network connectivity and problems regarding access to enterprise-wide systems.
• Assists users in utilizing technology to achieve business results via written documentation of procedures and one-on-one and/or documented resolutions.
• Assists entry-level help desk and operations personnel with technical problem resolution and serves as a mentor.
• Installs/maintains/supports specialized client applications for specific business users.
• Participates in various technological infrastructure projects, whether they are system rollouts, application upgrades, or new technology initiatives.
• Assists System Administrators with various tasks and/or projects as needed.
• Cross trains in day or nighttime operations, sometimes requiring overtime when necessary.
• Supports the company strategies and department goals by accomplishing tasks as assigned.
• Performs other duties and support tasks as assigned.

Benefits

• health, vision, and dental coverage
• a robust PTO plan
• an 8% employer contribution to retirement regardless of team member contribution
• educational assistance
• opportunities to participate in team member appreciation events
• STD, LTD and group life insurance 1X a team members salary
• free tickets to community attractions
• flexibility to thrive in a hybrid work environment
• opportunity to participate in development and volunteer programs

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: Associate degree