Property Management Software Support Specialist

Hillpointe•Maitland, FL

About The Position

WHY HILLPOINTE? Hillpointe is a fully integrated real estate development and investment management firm focused on developing market-rate workforce housing across the Sun Belt. Ranked at the top of NMHC's list of Builders and Developers, our team ensures best-in-class execution. Built on its long and proven track record of real estate development, the firm’s investment approach is centered around its in-house general contracting expertise, enabling direct control of cost and delivery timeframe. For each project, Hillpointe directly controls land acquisition, land development, construction, procurement of building materials, asset management, and capital markets. This is more than just a job - it's a career-defining opportunity! At Hillpointe, you'll be part of a dynamic, innovative team that has tangible impacts on day-to-day operations and contributes directly to overall success. PROPERTY MANAGEMENT SOFTWARE SUPPORT SPECIALIST The Software Support Specialist will serve as the primary point of contact for technical troubleshooting and system support across Hillpointe’s core platforms, including Funnel CRM, Entrata, and Skillpointe LMS. This role ensures smooth operations during the leasing and move-in process, supports prospects, onsite and regional teams with system issues, and provides timely resolution or escalation of technical problems.

Requirements

Prior experience in property management or property management system support required.
Strong troubleshooting and analytical skills.
Excellent communication skills for both technical and non-technical audiences.
Ability to manage multiple tickets/issues simultaneously and prioritize effectively.
Detail-oriented with strong documentation skills.
High school diploma or equivalent

Nice To Haves

Experience with Funnel, Entrata, or similar CRM/PMS platforms (strongly preferred).
Experience with Learning Management Systems (LMS), particularly login/access troubleshooting.

Responsibilities

Resolve technical issues across Funnel, Entrata, and Skillpointe login access
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.
Troubleshoot login and access issues for staff unable to access Skillpointe.
Reset or coordinate account access credentials as needed.
Escalate persistent login failures to LMS vendor (Grace Hill/Skillpointe).
Maintain a support ticket log with issue, root cause, resolution, and escalation notes.
Provide monthly summaries of top recurring issues, trends, and recommended process improvements.
Create and maintain FAQs, troubleshooting guides, and quick-reference resources for onsite staff.