Sr. IT Support Specialist (Sentry Credit) Job at TrueML in Everett

TrueML is seeking a highly motivated and experienced Sr. IT Support Specialist & Systems Administrator to join our TrueAccord team. This hybrid role requires deep technical expertise to perform advanced systems administration across a Windows-centric environment and a Mac-focused ecosystem, with 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.

$65,000 - $78,000 a year

In addition to salary, we offer

• Unlimited Paid Time Off & Paid Volunteer Time Off.
• Medical/dental/vision insurance.
• 401k through Charles Schwab.
• Flexible Spending Account, Limited FSA and Health Savings Account- with an eligible health care package.
• Company-paid short-term and long-term disability plus basic life insurance.
• Family-friendly maternity and paternity leave.
• Employee assistance program (EAP) via Claremont. Get free short-term counseling for mental health, free + discounted legal consultations, free financial consultations, access to work/life consultants, and more!
• Wellness Coach for you and 5 family members. Wellness Coach gives all TrueML employees access to 3000+ on-demand sessions about meditations, fitness, nutrition, and more!
• PerkSpot discount program. PerkSpot offers exclusive discounts to 900+ merchants nationwide, and has exclusive discounts up to 60% on hotels worldwide.