Senior Property Management Software Support Specialist

SENIOR SOFTWARE SUPPORT SPECIALIST

The Sr. Software Support Specialist is a member of the Software Support and Centralized Operations team, serving as the primary point of contact for technical troubleshooting and system support across Hillpointe's core platforms, including Funnel CRM, Entrata, and other business-critical applications that support operations across the organization. This role ensures the seamless operation of leasing, application, and move-in workflows by providing technical support to prospects, onsite teams, regional teams, and internal departments. The Sr. Software Support Specialist mentors junior team members, resolves complex technical issues, and escalates system concerns when appropriate to ensure timely resolution. As a member of the Centralized Operations team, this position also provides cross-functional support to multiple departments as business needs require, helping maintain operational efficiency and a consistent customer experience.

This position reports to the Implementation and Training Manager.

Key Responsibilities:

• Assist Technical Support Specialist Lead with training initiatives for Customer Care/Contact Center team and Support associates on Funnel, Entrata, and Skillpointe systems and processes.
• Mentor and provide day-to-day guidance to Support Specialists, serving as an escalation point for complex or unresolved tickets.
• Resolve technical issues across CRM, PMS, and supplemental software access/troubleshooting.
• Troubleshoot payment and promo code issues, duplicate charges, and failed processing between Funnel and Entrata.
• Manage document-related issues (missing forms, failed uploads, lease packet errors).
• Diagnose data sync errors (guest card not transferring, co-applicant not syncing, status stuck, duplicates created).
• Resolve notification/communication issues (emails not delivered, duplicate reminders, SMS failures).
• Ensure proper permissions and access levels for team members; deactivate accounts for terminated employees.
• Monitor and resolve Funnel helpdesk tickets (e.g., phones not connecting, quotes not generating, guest card glitches, reporting bugs).
• Serve as first line of support for property-specific Funnel issues reported by onsite teams.
• Track, document, and escalate recurring Funnel system bugs to vendor support as needed.
• Reset or coordinate account access credentials as needed.
• Escalate persistent login failures to Vendors, run support tickets as needed
• Maintain a support ticket log with issue, root cause, resolution, and escalation notes.
• Create and maintain FAQs, troubleshooting guides, and quick-reference resources for onsite staff and the training curriculum.
• Partner with direct manager/team lead to track ongoing CRM/PMS software issues

Qualifications:

• 2+ years of experience in software support, IT helpdesk, or property management system support (required).
• Strong working knowledge of Funnel, Entrata, or similar CRM/PMS platforms (required).
• Advanced troubleshooting and analytical skills, with the ability to identify root causes and systemic trends.
• Excellent communication skills for both technical and non-technical audiences.
• Demonstrated ability to assist with training content
• Ability to manage multiple tickets/issues simultaneously and prioritize effectively across a team.
• Detail-oriented with strong documentation skills.
• High school diploma or equivalent required; Associate's or Bachelor's degree preferred.

Physical Requirements:

• Ability to sit for extended periods of time while working at a computer or participating in meetings.
• Frequent use of hands and fingers to operate a computer, keyboard, mouse, phone, and other office equipment.
• Ability to communicate clearly and effectively verbally and in writing.
• Ability to hear and speak sufficiently to participate in meetings, conference calls, and presentations.
• Ability to view computer screens and read detailed reports, data, and documents for extended periods.
• Occasional ability to stand, walk, bend, or reach within an office environment.
• Ability to lift or move up to 15 pounds occasionally (e.g., laptops, documents, or office materials).
• Ability to maintain focus, concentration, and decision‑making capacity in a fast‑paced, high‑volume operational environment.
  
  

Work Environment:

• Primarily works in a professional office environment, which may be onsite, hybrid or remote depending on business needs.
• Extensive use of computers, telecommunication systems, and contact center technology platforms.
• Regular participation in meetings, presentations, and virtual conferences
• Work schedule is generally business‑hour based but may require extended hours, evenings, or weekends as needed to support operational demands, peak periods, or critical initiatives.
• Occasional travel may be required for site visits, leadership meetings, or professional development.
• Frequent interaction with employees, vendors, and internal departments in advisory capacity.