Regional IT Support Specialist

The Regional IT Support Specialist is a field-based, customer-facing IT generalist role supporting approximately six communities. Reporting to the Corporate Director of IT, this position is accountable for inventorying and resolving technology issues across assigned communities, managing tickets in Zendesk, providing hands-on endpoint and basic network support, and building strong partnerships with community leadership, residents, and staff., * Conduct comprehensive on-site IT inventories and audits at each assigned community: hardware assets (desktops, laptops, printers, peripherals, mobile devices), network infrastructure (Wi-Fi, switches, guest/secure networks), software in use, pain points, and recurring issues.

• Maximize current technology utilization with the local systems at each location.
• Create, triage, resolve, and document Zendesk tickets for community-reported issues; establish clear escalation paths to Corporate IT and track Service Level Agreements.
• Provide hands-on, on-site and remote support for staff endpoints, printers, basic networking/Wi-Fi troubleshooting, Microsoft 365, and common business applications.
• Document current-state processes, identify quick wins, and draft SOPs and knowledge base articles.
• Build strong relationships with community leadership team and frontline team members; understand unique workflows and resident populations at each site.
• Support any existing resident technology requests on an ad-hoc basis while the formal program is designed.
• Help to develop service catalog, pricing model (e.g., one-time move-in packages billed to resident statement or family, hourly support packages, monthly support subscriptions), and recommendations with community operations.
• Create resident-facing onboarding checklists and satisfaction feedback mechanisms.
• Train and upskill select community team members to handle first-level resident tech questions, with clear escalation to the Regional Specialist.
• Identify high-volume, repetitive tasks and create documentation for self service support and resolution.
• Contribute to broader Dial technology strategy as a field subject-matter expert; participate in vendor evaluations, standards development, and cross-community projects.
• Mentor and develop any future regional or community-level tech support resources.

This is an evolving role with solid growth potential. After an initial stabilization phase, the Specialist will help design, pilot, and rollout of a Resident Technology Support Program. The role also includes identifying and helping implement practical agentic AI and automation solutions to improve efficiency for staff and enhance technology experiences for residents. The ideal candidate combines strong technical troubleshooting breadth, outstanding interpersonal skills (especially with seniors and non-technical users), organizational discipline for multi-site work, and a forward-looking mindset toward automation and service innovation., * 3+ years of progressive, hands-on IT support experience, with at least 1 year in multi-site, field, or regional support roles

• Exceptional interpersonal skills, active listening, empathy, and the ability to explain technical concepts in plain language.
• Proven leadership, people management, influencing and motivating skills and the ability to manage complex issues.
• Maintain confidentiality of verbal and written information pertaining to residents, community operations and personnel.
• Ability to travel across regional geography to support communities and attend various meetings.
• Comfortable working independently across multiple sites with minimal direct supervision.
• Strong organizational skills for managing travel, tickets, documentation, and competing priorities.
• Prior work in senior living, assisted living, healthcare, hospitality, or other customer-intensive, multi-location environments is strongly preferred.
• Demonstrated success supporting non-technical users (especially older adults or families) with patience and clarity
• Strong troubleshooting across Windows/macOS endpoints, printers, mobile devices (iOS/Android), Wi-Fi/networking basics, Microsoft 365, and common peripherals.
• Comfortable learning new systems quickly (Yardi, LifeLoop, Zendesk, etc.)
• Not expected to be a deep infrastructure or cybersecurity specialist-the role partners closely with Corporate IT for escalation.
• Curiosity and demonstrated ability to identify practical applications for agentic AI, automation tools (e.g., Zendesk AI features, Microsoft Power Automate, no-code agents), and process improvement. Not a developer role, but someone who can “see the automation opportunity” and help pilot solutions.

Education and Certifications

• CompTIA A+ (strongly recommended); CompTIA Network+ or equivalent networking fundamentals; ITIL Foundation or Zendesk-specific training a plus

Pulled from the full job description

• Referral program
• Tuition reimbursement
• Prescription drug insurance
• AD&D insurance
• 401(k)
• Health insurance
• 401(k) matching, * Birthday & anniversary PTO
• Tuition Assistance
• Double pay on holidays
• PTO accrual on DAY 1
• Referral Bonus
• Loyalty Incentive
• Employee Recognition Program
• Pay Advance Program
• Medical and Prescription Drug Insurance including Dental and Vision
• Basic Term Life/AD&D
• 401k

Pay: $75,000.00 - $80,000.00 per year, * 401(k) matching

• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Tuition reimbursement
• Vision insurance