Sr. Desktop Support Specialist

Community. Security. Trust. This is the foundation on which Bluestone Bank is built. We've helped Southern New England prosper for over 150 years by providing responsible, relevant, and secure financial solutions. Whether our customer’s unique needs include finding a safe place to grow their savings, financing their next home, protecting their future, or building their business, we are here to help them reach their goals. Let’s get there, together!

In addition to being a great place to bank, Bluestone Bank is a great place to work! Named by the Boston Business Journal as a Best Places to Work in 2025, you are joining a team that cares about your career success and will also receive:

• A competitive salary with performance-based incentives.
• Comprehensive medical with deductible reimbursement, dental, and vision coverage. 
• An employer matching 401k plan. 
• Training and professional development opportunities, including tuition reimbursement. 
• Work life balance with paid time off, paid volunteer hours, and 11 paid holidays. 

The Senior Desktop Support Specialist, under the direction and training of the VP, IT Manager, serves as a senior-level technical resource ensuring that systems, software applications, workstations, printers, network communications devices, and general office systems operate efficiently to provide users with a high level of service while adhering to established information technology policies, standards, and procedures. This position assumes advanced responsibilities for workstation installations and installation of pre-defined hardware, cabling, and software configurations, and provides escalation-level support for complex desktop, endpoint, and peripheral issues. The Senior Desktop Support Specialist assists with problem resolution, issue tracking, and monitoring of the helpdesk ticket queue with prioritization of efforts under guidelines provided by the VP, IT Manager. This role also acts as a technical mentor and escalation point for junior IT support staff, provides backup support for core banking system operations, and contributes to network and systems administration tasks in the absence of the Systems Administrator.

Essential Functions

Reasonable accommodations may be made to enable individuals with disabilities to perform these essential functions.

Desktop Support & Helpdesk Operations

• Provides senior-level first and second-tier contact to resolve user issues, escalating tickets as needed to the appropriate IT personnel, and mentoring junior support staff on troubleshooting methodology.
• Provides advanced assistance and support to users for routine and complex telephone equipment issues, printer and copy machine support, bank email system(s) support, general file access administration, and workstation software/hardware support, including repair, moves, installations, deployments, and upgrades.
• Manages Active Directory and endpoint administration for 100+ employees and devices across 11+ locations, including user account creation, group provisioning, and access controls.
• Assists with user password resets, domain user administration, and general user administration of various applications as directed by the VP, IT Manager.
• Assists with the installation and support for general software applications (Microsoft 365, Adobe, Windows, etc.) and Core Banking software.
• Provides support and problem resolution for secure email solutions and web browser certificate installations.
• Deploys new laptops and endpoints via imaging, onboarding processes, and the network change control process across 200+ endpoints on the bank’s network.
• Troubleshoots and resolves technical issues ranging from workstations, servers, and network connectivity.

Systems & Network Support

• Maintains and monitors the IT RMM system daily, including patch and software updates, ticketing, and endpoint health.
• Reviews and remediates vulnerabilities via the bank’s vulnerability management software.
• Provides basic support for the bank’s Wi-Fi network in the absence of the Network Administrator.
• Assists with virtual machine creation and monitoring via the VM Hypervisor system.
• Supports core banking system operations and assists with troubleshooting in the absence of the Core Banking Solutions & System Administrator.
• Assists with VPN administration, configuration, and remote/on-site troubleshooting to ensure secure connectivity.

Administrative & Asset Management

• Tracks software and system upgrades and maintains and updates the IT Asset Inventory database as needed.
• Maintains and monitors the IT Ticketing system and job queue.
• Orders office supplies and general computer parts as needed.
• Creates and maintains documentation on IT systems and cross-trains other IT staff members to step in when needed.
• Completes the IT daily checklist in the absence of the Senior Systems Administrator, including validation of nightly server backups, antivirus updates, Windows and non-Windows updates, server capacity status, secure email, and other operating system updates.

Projects & Leadership

• Serves as a key contributor on bank-wide IT projects, including VoIP phone system conversions, Microsoft 365 migrations, VPN migrations, and Wi-Fi network deployments.
• Leads device logistics, user/group provisioning, and coordinated deployment across multiple branch locations for major IT initiatives.
• Develops internal documentation and end-user setup guides to standardize implementation processes.
• Provides technical mentorship and guidance to junior desktop support and helpdesk staff.

Availability & Other Duties

• Availability for Saturday on-call support rotation as scheduled by the VP, IT Manager. Additionally, there will be times when special projects are scheduled to be completed outside of standard operating hours, including evening, weekend, or early morning hours.
• Available to travel to remote branch locations to assist users in resolving issues that cannot be fixed remotely or perform other IT-related tasks.
• Performs additional duties as requested.

The pay range for this position is $29.00 to $32.00 per hour and is the lowest to highest salary we in good faith believe we would pay for this role at the time of this posting. We may ultimately pay more or less than the posted range, and the range may be modified in the future. An employee’s pay position within the salary range will be based on several factors including, but not limited to, relevant education, qualifications, certifications, experience, sales or revenue-based metrics, and business or organizational needs and affordability.

Physical Demands and Work Environment

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

While performing the duties of this job, the employee is regularly required to sit and talk or hear, reach with hands and arms; and stoop, kneel, or crouch. The employee must occasionally lift and/or move up to 50 pounds. Specific vision abilities required by this job include close vision, distance vision, peripheral vision, and the ability to adjust focus.

An Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, pregnancy, genetic information, disability, status as a protected veteran, or any other protected category under federal, state, and local laws. 

• High School Diploma or equivalent required; Associate’s or Bachelor’s degree in Information Technology, Management Information Systems, or a related field is strongly preferred.
• Three to five years of progressive desktop support experience in a professional environment, preferably in the financial services industry.
• CompTIA A+ certification required; CompTIA Network+, Security+, or other equivalent certifications are a plus.
• Demonstrated experience with Active Directory, Group Policy, Microsoft 365 Admin Center, endpoint management tools (e.g., Ivanti, Sentinel One, Mimecast), and DUO/MFA administration.
• Working knowledge of VPN, DNS, DHCP, Wi-Fi deployment, and endpoint/server connectivity.
• Proficiency with hardware diagnostics and component-level troubleshooting across Windows endpoints, mobile devices, printers, A/V equipment, and physical servers within a multi-site environment.
• Experience with Python scripting (basic), CMD, or similar tools is a plus.
• Knowledge of industry regulations and compliance requirements applicable to the banking/financial services sector.
• Excellent analytical, problem-solving, and decision-making skills.
• Strong interpersonal and communication skills with a positive attitude and willingness to assist end users in a timely manner.
• A general understanding of IT security principles and strong organizational skills are required.
• Ability to work independently and as part of a team, with the capacity to mentor and guide junior staff.

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