Freelance Script Coverage Assistant Jobs in Florida

Location: Lake Mary, FL
Compensation: (based on experience and certifications)

Overview

Kappa Computer Systems is seeking a Observability Systems Associate (Observability, Site Reliability & Endpoint Assurance) to support the reliability, visibility, and consistency of managed client environments. This role focuses on system monitoring, endpoint validation, alert management, and automation to ensure systems remain secure, stable, and fully observable.
This is an operationally focused role with growth opportunities into Site Reliability Engineering, Systems Engineering, or Security Engineering.

You'll help improve the overall health and efficiency of our monitoring systems by optimizing RMM automations, refining alerts, integrating our stack and ensuring accurate system visibility.

This position is ideal for a technician who enjoys scripting, integrating systems and maintaining stable, secure, and well-documented client environments.

Key Responsibilities

Monitoring & Reliability Operations

• Perform daily monitoring reviews across observability and security platforms.
• Identify, triage, and remediate alerts within scope; escalate critical issues appropriately.
• Analyze alert patterns to identify recurring issues, reliability risks, and improvement opportunities.
• Assist with tuning alert thresholds to reduce noise and improve detection accuracy.

Endpoint Validation & Software Assurance

• Ensure all managed endpoints have required monitoring, security, and management software installed and actively reporting.
• Compare agent and software counts across platforms (RMM, security, identity, and monitoring tools) to identify discrepancies, stale devices, or missing coverage.
• Validate endpoint compliance with Kappa's baseline standards and document exceptions.
• Assist with remediation by repairing, reinstalling, or escalating issues related to missing or malfunctioning agents.
• Support standardized onboarding by verifying new endpoints receive proper tools, configurations, and monitoring automatically.

Scripting, Automation & Platform Integration

• Develop and maintain basic scripts (PowerShell, Python, or similar) to automate endpoint checks, data collection, and routine operational tasks.
• Assist with integrating data across multiple systems to improve visibility and reporting.
• Support senior engineers by testing and refining scripts used for proactive remediation and system standardization.
• Help automate compliance checks and policy enforcement related to endpoint configuration and security posture.

Reporting & Documentation

• Generate and maintain reports related to:
  • Endpoint coverage and agent health
  • Alert trends and system reliability
  • Security and compliance gaps
• Correlate data from multiple platforms to identify risks and optimization opportunities.
• Document all work accurately in Halo and internal systems.

Professional Development & Collaboration

• Participate in ongoing training related to observability, reliability engineering, security, and automation.
• Contribute to improvements in monitoring standards, endpoint baselines, and operational workflows.
• Collaborate with Systems Administrators, Systems Engineers, and the Help Desk team to support client success.
• Participate in weekly team meetings and regular 1-on-1 development discussions.

Other Duties

• Answer incoming phone calls and assist with client inquiries or ticket creation.
• Receive and organize shipments, maintaining inventory and distributing hardware or supplies as needed.
• Support the help desk team when required, including ticket triage, basic troubleshooting, and device setup.
• Watch training videos and attend classes to learn new technologies and discover ways to improve our tool stack and processes.

A continuous learning mindset is highly valued in this role.

Requirements

• 1-3 years of experience in IT support, help desk, or system/network monitoring.
• Experience with PowerShell scripting.
• Hands-on experience supporting PCs, servers, networks, and firewalls.
• Familiarity with RMM and PSA tools (e.g., N-able, ConnectWise, Halo, Datto, NinjaOne, etc.).
• Understanding of backups, antivirus, patch management, and endpoint protection.
• Working knowledge of networking fundamentals and firewall troubleshooting.
• Strong attention to detail, documentation accuracy, and adherence to process.
• Excellent communication and organizational skills.
• Team-oriented with a proactive, customer-focused approach.

Preferred Experience

• Previous experience within a Managed Service Provider (MSP).
• Exposure to MDR, SIEM, and vulnerability management platforms.
• Familiarity with Windows Server, Active Directory, and common network device interfaces.
• Experience fine-tuning RMM alerts, thresholds, and PowerShell-based automations.
• Understanding of system health, patch compliance, and proactive maintenance best practices.

Why Work With Us

• Established & Trusted: Join a well-established Managed Service Provider with over 25 years in business and a proven record of stability and client success.
• Award-Winning Culture: Proudly recognized as one of the Best Places to Work for five consecutive years, reflecting our commitment to employee satisfaction and workplace excellence.
• Great Benefits: Enjoy a 3% company retirement match, paid holidays (including your birthday!), and generous paid time off (PTO).
• Supportive Environment: Thrive in a collaborative, team-driven atmosphere where communication, documentation, and continuous learning are encouraged.
• Work-Life Balance: We believe in sustainable workloads and predictable schedules-no chaotic ticket queues or burnout culture.
• Engaged Workplace: Take part in company outings, enjoy office snacks, and be part of a team that values both professional growth and camaraderie.
• Opportunities to Grow: Gain exposure to a wide range of technologies with a company that actively invests in your career development and advancement.