Sr. IT Support Specialist (Sentry Credit)
TrueAccord
IT, Customer Service
Everett, WA, USA
Posted on Sep 6, 2025
TrueML is seeking a highly motivated and experienced Sr. IT Support Specialist & Systems Administrator to join our TrueAccord team. In this critical, hands-on role, you will be instrumental in maintaining and optimizing our IT infrastructure, serving as a technical pillar for both the existing Windows-centric environment at Sentry and the Mac-focused ecosystem of TrueML. This hybrid role requires deep technical expertise to perform advanced systems administration, coupled with a passion for mentorship to guide and elevate junior support staff. The ideal candidate is a proactive problem-solver and a strong communicator, dedicated to ensuring the reliability, security, and efficiency of our IT operations.
What You'll Do:
- Coach and mentor junior IT support staff, fostering a collaborative environment.
- Serve as a primary escalation point for complex IT support issues, providing advanced troubleshooting and resolution for hardware, software, and network problems.
- Develop and maintain clear documentation for system administration, operating procedures, and best practices to serve as a resource for the entire team.
- Be an advocate for knowledge sharing across the IT department, providing training to team members as necessary.
- Administer, secure, and maintain the company's core Windows-based infrastructure with experience in Microsoft 365, Azure, Entra, and SharePoint.
- Support and troubleshoot Mac OS and ChromeOS environments, including the administration of MDM technologies (JAMF/Google).
- Manage and administer identity provider (IdP) and directory services (Okta).
- Configure, maintain, and troubleshoot network infrastructure, including LAN, WAN, VPN, firewalls, and switches.
- Automate routine IT tasks and workflows using AI, scripting, and APIs to improve operational efficiency.
- Monitor system performance, proactively identifying and resolving potential issues to ensure high availability and reliability.
- Integrate IT operations with security tools and policies, enforcing best practices for data protection and compliance in a highly regulated financial services environment.
- Participate in and support IT projects from initiation to completion, including system upgrades, migrations, and new technology rollouts.
Skills & Experience
- Minimum of 5+ years of progressive experience in IT, with demonstrated expertise in a mixed Windows and Mac enterprise environment.
- Advanced administration experience with Microsoft 365, Azure, Entra, and other Microsoft cloud services.
- Hands-on experience with Mac OS administration and MDM technologies.
- In-depth knowledge of identity management, networking principles (TCP/IP, DNS, DHCP), and security best practices.
- Familiarity with cloud-based infrastructure (AWS is a plus).
- Excellent troubleshooting and problem-solving skills.
- Experience working in a SaaS environment is highly desirable.
- Proven ability to mentor, coach, and provide constructive feedback to junior team members.
- Exceptional customer service, interpersonal, and communication skills—ability to remain helpful and calm under pressure.
- Excellent analytical, troubleshooting, and problem-solving abilities.
- A proactive attitude and service-oriented mindset, with the ability to work independently in a fast-paced and evolving environment.
What Will Make You Stand Out
- Relevant industry certifications (e.g., CompTIA Security+, Network+, Server+, AWS Certified SysOps Administrator – Associate).
- Experience with the ITIL framework.
- Knowledge of ISO 27001 and NIST frameworks.
- Experience with monitoring and logging tools.