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Sr. IT Support Specialist (Sentry Credit)

Trueml · Everett, United States Of America · Onsite

$65,000.00  -  $78,000.00

  • Senior
  • Office in Everett
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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.


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.


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.