Senior technical leader responsible for administering, securing, and optimizing Microsoft 365 GCC High and Azure Government environments, ensuring compliance with NIST SP 800-171 and DoW CMMC Level 2 standards.
Responsibilities
Administer Microsoft 365 GCC High and Azure Government infrastructure
Maintain security configurations and access policies
Implement MFA, Conditional Access, PIM, and endpoint compliance
Develop automation scripts with PowerShell, Microsoft Graph, and Power Automate
Administer and support Microsoft Azure systems, manage physical and virtual servers, network infrastructure, and provide advanced technical assistance to users.
Responsibilities
Administer and support Microsoft Azure systems, including SharePoint, Exchange, and Teams.
Manage and maintain physical and virtual servers, including hardware and software configurations.
Install, configure, and update operating systems and applications.
Monitor server performance and resource utilization to sustain reliability.
Implement and test system backup and disaster recovery procedures.
Requirements
Bachelor’s degree in Computer Science, Information Technology, or a related field
The Microsoft Platform Engineer serves as the technical SME and solution owner for our Microsoft 365 E5 and endpoint management ecosystem. This role will own the design, implementation, optimization, administer, and operational maturity of Microsoft 365 Apps (Exchange, Teams, Defender, Purview, Insights etc.), Intune, SCCM, application catalog services, endpoint compliance, and cloud patch management.
Compensation
The base salary range for this position is $145,000 - $155,000 on a full-time schedule. Along with base compensation, Trupanion employees are currently eligible for monthly bonuses. We want all employees to be invested in Trupanion’s success, so we grant Restricted Stock Units to all new team members. Our new hire grants vest over 4 years.
Responsibilities
Serve as the technical SME and principal engineer for Microsoft 365 E5 services
Own the engineering, configuration, governance, and operational support of Microsoft Office applications
Evaluate existing Microsoft 365 E5 capabilities and identify opportunities to improve adoption, security, automation, compliance, and cost efficiency
Partner with business stakeholders to understand productivity needs and translate them into secure, scalable Microsoft platform solutions
Develop standards, best practices, and platform governance for Microsoft 365 service configuration and usage
The Senior Systems Engineer will lead the design, administration, and continuous improvement of a complex enterprise systems and compute environment, focusing on maintaining secure, reliable, and high-performing infrastructure.
Compensation
Hourly compensation of $65–$75 per hour.
Responsibilities
Design, implement, administer, and maintain enterprise systems, including Microsoft Exchange, physical and virtual servers, Active Directory, Group Policy, Certificate Services, authentication platforms, compute, networking, storage, and remote access services.
Manage and support cloud-based infrastructure and services, including Microsoft Azure, Entra ID, and Office 365.
Administer and optimize Citrix Virtual Desktop Infrastructure (VDI), load balancers, and SSL certificate management.
Monitor and continuously improve system performance, availability, scalability, and security.
Perform routine, scheduled, and long-term infrastructure maintenance while maintaining high operational and service standards.
Requirements
Bachelor's degree in Computer Science, Computer Information Systems, or a related field preferred
Operate CTI platforms and feeds to analyze adversary activity, translate cyber threat data into actionable intelligence, produce written intelligence products, map real-observed TTPs to named adversary groups, conduct malware, infrastructure, and network analysis, and perform dark‑web collection tradecraft.
Locations (2)
Florida, United States
United States
Compensation
Pay Range: $50 - $60/hour.
Responsibilities
Operate CTI platforms and feeds to analyze adversary activity
Translate cyber threat data into actionable intelligence and operational detections
Produce written intelligence products with a Bottom Line Up Front (BLUF), assessment, confidence level, and recommendations
Map real‑observed TTPs to named adversary groups using MITRE ATT&CK framework
Conduct malware, infrastructure, and network analysis, along with dark‑web collection tradecraft
Take point on the company's CMMC and CUI compliance program and its day-to-day security operations, working alongside the Systems Administrators and Helpdesk to keep a defense contractor's environment secure and audit-ready.
Compensation
The likely salary range for this position is $110,000 to $150,000.
Responsibilities
Serve as the company lead for CMMC Level 2 and NIST SP 800-171 compliance: maintain the System Security Plan (SSP), Plans of Action and Milestones (POA&Ms), and SPRS score, and prepare the company for its CMMC third-party (C3PAO) assessment.
Own the identification, marking, handling, and flow of Controlled Unclassified Information (CUI), including the CUI boundary across the Microsoft 365 GCC High tenant and on-premises systems.
Serve as the primary point of contact for the Arctic Wolf Managed Detection and Response (MDR) service: triage and respond to alerts and escalations, maintain sensor and agent coverage, and track findings to closure.
Administer Microsoft Defender (Endpoint, Office 365, Identity, and Cloud Apps) and Microsoft Secure Score: tune policies, investigate incidents, and drive remediation of recommendations.
Run the vulnerability management program: review scan results, prioritize findings by risk, coordinate patching with the Systems Administrators, and verify remediation.
Requirements
Bachelor's degree in Cybersecurity, Information Technology, or a related discipline
The Senior Systems Engineer (Microsoft Infrastructure) is a subject matter expert across Microsoft technologies, responsible for architecting, maintaining, and supporting enterprise-grade systems and services.
Compensation
*Pay Range: $80,000 - $130,000 USD annually
Responsibilities
Architect, deploy, and maintain Microsoft-centric infrastructure
Manage adjacent infrastructure such as license servers, proxies, and SMTP relays
Contribute to reporting and documentation efforts
Assist with datacenter operations including racking, cabling, and hardware lifecycle
Collaborate with IT, support, and engineering teams
Requirements
Bachelor's in Computer Science or equivalent
Nice to have: Post-production or media environments experience
VMware Virtualisation Infrastructure Specialist with advanced VMware administration and troubleshooting expertise to support complex virtualisation environments, focusing on VMware vSphere 7.x and 8.x, VCF 9.0, VxRail, vCenter and ESXi, alongside disaster recovery and infrastructure operations.
Responsibilities
Administer and troubleshoot VMware vSphere 7.x and 8.x, VCF 9.0 and VxRail environments
Support VMware SRM (Site Recovery Manager) 8.1 and VMware Aria administration and troubleshooting
Diagnose and resolve critical VMware ESXi and vCenter issues, and support vCenter and ESXi upgrades
Work with DRS, HA, vSwitch, dvSwitch, ESXCLI and ESXTOP
Extract and analyse vCenter reports and produce performance-analysis reports across virtualisation components
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