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.
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