Senior Software Support Specialist

Hillpointe•Maitland, FL

3d•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

Associate's or Bachelor's degree preferred.

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