Company

Argo and Farm Family are specialty property and casualty insurance brands whose underwriting companies are wholly-owned subsidiaries of Clearbrook Holdings Inc. Argo and Farm Family partner with agents and brokers to provide insurance solutions that enable businesses to manage risks with confidence.

Job Description

The IT Service Desk Supervisor is responsible for the overall operational health, performance, and maturity of the Service Desk function. This role provides direct people leadership, oversees 24x7 support operations (including overnight coverage), serves as an escalation point for complex and critical incidents, and drives continuous improvement initiatives such as shift‑left adoption, knowledge maturity, and access management process adherence.

The Supervisor ensures consistent service delivery aligned to SLA, ITIL, security, and audit requirements, while fostering a high‑performing, customer‑focused support team.

KEY RESPONSIBILITIES

People Leadership & Supervision

• Directly supervise, coach, and mentor Service Desk Analysts
• Provide oversight and leadership for overnight Service Desk staff, including agents supporting after-hours operations
• Support onboarding, training, scheduling, performance management, and professional development for all direct reports
• Conduct regular performance check‑ins, evaluations, and coaching sessions
• Assist with hiring and scaling efforts, including preparation for the addition of new hires to the team
• Ensure staffing models support 24x7 operational coverage, service quality, and compliance with labor guidelines

Operational Oversight (24x7 Service Desk)

• Oversee daily Service Desk operations including incident, request, and queue management
• Ensure accurate ticket logging, prioritization, documentation, and lifecycle management
• Monitor adherence to SLA, response times, resolution targets, and quality standards
• Actively review trends related to missed opportunities, escalations, and repeat issues
• Serve as a primary escalation point for complex, high-impact, or sensitive issues

Escalation & Incident Management

• Act as an escalation point for critical incidents and major service disruptions
• Coordinate with technical teams, security, IAM, vendors, and leadership during incidents
• Ensure timely, accurate, and consistent communication to users and stakeholders during outages
• Participate in incident reviews and root cause discussions, identifying prevention opportunities

Shift‑Left, Knowledge & Continuous Improvement

• Drive shift‑left initiatives to increase first‑contact resolution and reduce dependency on higher-tier teams
• Ensure analysts resolve eligible incidents and requests using approved Knowledge Base (KB) articles
• Identify recurring issues suitable for:
  • Knowledge creation or refinement
  • Automation or self-service enablement
  • Process improvement
• Promote Knowledge-Centered Service (KCS) behaviors and KB contribution expectations

User Access Management (UAM) Oversight

• Provide supervisory oversight for baseline UAM activities performed by the Service Desk, including:
  • Identity verification and user validation
  • Password resets, account unlocks, and approved access requests
• Ensure all access-related work complies with least privilege principles, documented approvals, and audit standards
• Partner with IAM, Security, and application teams on escalations or exception handling
• Monitor access-related incident trends and drive improvements to reduce risk and rework

Metrics, Reporting & Leadership Communication

• Monitor and analyze Service Desk performance metrics (e.g., SLA, FCR, CSAT, backlog, escalation rates)
• Prepare operational reports, leadership summaries, and improvement recommendations
• Use data to identify gaps in staffing, process, training, or tooling
• Communicate operational risks, constraints, and improvement plans to management and stakeholders

Process, Policy & Compliance

• Ensure Service Desk operations adhere to ITIL practices, company policy, and security requirements
• Maintain and enforce standard operating procedures (SOPs)
• Support audit and compliance activities through accurate documentation and defensible processes
• Reinforce consistent execution across daytime and overnight teams

POSITION REQUIREMENTS

Required

• Associate’s degree in information technology, computer science, or equivalent relevant experience
• Prior experience in a Service Desk or IT Support role, including escalation handling
• Demonstrated people leadership or supervisory experience
• Strong understanding of ITIL based service management
• Experience managing high volume, 24x7 support environments
• Excellent verbal and written communication skills
• Strong problem solving, organizational, and decision-making abilities
• Experience working with ITSM platforms (e.g., ServiceNow)

Preferred

• Certifications such as:
  • ITIL
  • CompTIA A+, Network+, Security+
  • Microsoft (MCSA/MCSE)
• Experience supporting executive users
• Experience leading or influencing shift-left initiatives
• Familiarity with identity and access support processes

Core Competencies

• Leadership & accountability
• Operational discipline
• Collaboration across teams and vendors
• Data driven decision making
• Strong customer focus
• Clear and professional communication
• Continuous improvement mindset

Core Values

• Desire to excel
• Commitment to clients and teammates
• Courage to do the right thing
• Apply original and critical thinking

Compensation

 $75,000 - $85,000

PLEASE NOTE: 

Applicants must be legally authorized to work in the United States. At this time, we are not able to sponsor or assume sponsorship of employment visas.

If you have a disability under the Americans with Disabilities Act or similar state or local law and you wish to discuss potential reasonable accommodations related to applying for employment with us, please contact our Benefits Department at 210-321-8400. 

Benefits and Compensation

We offer a competitive compensation package, performance-based incentives, and a comprehensive benefits program—including health, dental, vision, 401(k) with company match, paid time off, and professional development opportunities.

Core Values

At Clearbrook our Core Values are Integrity, Collaboration, Pursuit of Excellence and Forward Thinking. These values reflect who we are today and who we aspire to be - guiding how we work, how we lead and how we succeed.