Property Operations & Technology Manager

Hillpointe•Winter Park, 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. People Operations & Technology Manager The People Operations & Technology Manager position owns the design, execution, and continuous improvement of HR processes and systems that support a consistent, compliant, and high-quality employee experience. This role serves as the operational and technology backbone of the HR organization – translating strategy into scalable workflows, system governance, and data-driven insights. The People Operations & Technology Manager operates as both a people leader and systems owner, ensuring HR programs are intuitive, efficient, audit-ready, and aligned with business growth.

Requirements

Bachelor’s degree in Human Resources, Business, or related field (Master’s preferred).
5–7 years of progressive HR experience with strong emphasis on operations, systems, and governance.
Demonstrated experience leading HR technology implementations, integrations, and platform optimization.
Proven success conducting gap analyses, audits, and operational assessments.
Strong change management, vendor management, and cross-functional collaboration skills.
Advanced competency in workflow design, documentation, analytics, and reporting.

Nice To Haves

Previous experience with UKG Ready is preferred.

Responsibilities

Define operating rhythms, prioritization frameworks, and workflow accountability across People Operations.
Lead, coach, and develop the HR Generalist and Senior HR Generalist team, establishing clear ownership models, service standards, and escalation frameworks.
Oversee employee relations, workforce programs, performance management, compliance, and organizational change activities executed by the HR Generalist team, ensuring consistency, professionalism, and adherence to legal and organizational standards.
Establish standardized frameworks, policies, templates, training, and documentation to support HR Generalists in managing investigations, disciplinary actions, performance documentation, leave administration, workers’ compensation, accommodations, and regulatory requirements.
Govern the performance management lifecycle - including goal setting, check-ins, reviews, calibration, and documentation, ensuring tools and workflows are intuitive, well-adopted, and manager-friendly.
Lead change management governance for new policies, systems, and workforce programs by defining communication strategies, training requirements, readiness assessments, and adoption metrics.
Monitor trends, risk indicators, performance outcomes, and change adoption metrics through dashboards and reporting to proactively identify gaps, risks, and improvement opportunities.
Ensure all workforce, performance, and compliance processes remain audit-ready, well-documented, and clearly communicated.
Serve as the senior point of governance and quality control for all People Operations deliverables.
Own the strategy, governance, and continuous optimization of Hillpointe’s HR technology ecosystem, including HRIS, ATS, performance management, learning, compliance, engagement, and workflow platforms.
Conduct regular gap analyses and audits of all HR technology platforms to evaluate utilization, data integrity, scalability, and alignment with business needs.
Partner with vendors and internal technical teams to configure systems, build enhancements, and develop custom API integrations where needed to streamline workflows and reduce manual effort.
Establish data governance standards and lead system integrations to ensure accurate, reliable, and timely workforce data across platforms.
Design, document, and maintain standardized HR workflows, SOPs, and process maps that balance compliance with usability and efficiency.
Implement departmental service-level agreements (SLAs) within workflow management and ticketing systems to track responsiveness, throughput, productivity, and quality.
Analyze workflow and service metrics to identify bottlenecks, inefficiencies, and improvement opportunities.
Lead recurring audits of HR processes to evaluate effectiveness, cycle time, and employee experience impact, deploying corrective actions and enhancements as needed.
Serve as a key operational partner to Payroll and Benefits, ensuring HR system transactions and process changes are executed with full awareness of downstream payroll and benefits impacts.
Collaborate on cross-system testing, reconciliations, and audits to maintain data accuracy, compliance, and operational continuity.