Director of Systems & Integrations

High Ground Services; Orlando (FL); Hybrid; USD 140,000 - 190,000; Full time

Job summary

High Ground Services seeks a Director of Systems & Integrations to lead design, implementation, and optimization of business systems across our Florida-based operations. You will oversee CRM, scheduling, billing integrations, and data governance to improve efficiency and customer experiences.

You will collaborate with operations, finance, sales, and field teams, manage vendor relationships, and drive technology investments to support growth across multiple locations.

Qualifications

• Strong analytical skills for data interpretation and process optimization.
• Expertise in systems integration, APIs, data synchronization between platforms.
• Proven project management with cross-functional teams and timelines.
• Proven team leadership with mentoring and stakeholder communication.
• Presales and stakeholder engagement to align technology with business needs.
• Experience with ERP, CRM, scheduling, and invoicing platforms preferred.
• Knowledge of data security, access control, and compliance best practices.
• Bachelor’s degree in IS/CS/Engineering/Business or related field; equivalent experience.

Responsibilities

• Oversee design, implementation, and optimization of business systems and integrations across operations.
• Lead evaluation and selection of software platforms (CRM, scheduling, billing, etc.).
• Develop standards for data management and reporting; ensure seamless system integration.
• Manage integration projects; coordinate with internal teams and external vendors.
• Troubleshoot system issues and identify opportunities to improve workflow and customer experience.
• Provide training and ongoing support; maintain documentation of processes and architecture.
• Plan future technology investments to support growth and multi-location operations.

Skills

Analytical skills

Systems integration

Project management

Team leadership

Stakeholder engagement

Data security

ERP/CRM familiarity

Education

Bachelor’s degree

Equivalent practical experience

Tools

ERP systems

CRM systems

Scheduling software

Billing platforms

Job description

Company Description High Ground Services is a Florida-based, veteran-owned commercial landscaping and outdoors company dedicated to keeping Florida businesses locally owned and operated. The company partners with and operates high-performing commercial landscaping companies where team members can grow their careers, customers receive exceptional service, and quality standards are consistently elevated. High Ground Services delivers reliable, high-quality landscape maintenance, large-scale property enhancements, and installation services that help Florida businesses and communities look their best. With a “People First, Customers for Life, Quality without Compromise” philosophy, the company emphasizes integrity, long-term relationships, and continuous improvement. Team members are encouraged to “take the High Ground” by choosing the right path, even when it is not the easiest or quickest.

Role Description The Director of Systems & Integrations is a full-time, hybrid role based at current HG locations, responsible for overseeing the design, implementation, and optimization of business systems and technology integrations across High Ground Services’ operations. This role leads the evaluation and selection of software platforms, ensures seamless integration between systems (such as CRM, scheduling, maintenance, and billing tools), and develops standards for data management and reporting. Day-to-day responsibilities include managing integration projects, coordinating with internal teams and external vendors, troubleshooting system issues, and identifying opportunities to improve workflow efficiency and customer experience. The Director will collaborate closely with operations, finance, sales, and field teams to align technology solutions with business goals, provide training and support, and maintain clear documentation of processes and system architecture. This position also plays a key role in planning future technology investments and supporting growth initiatives across the organization.

Qualifications

• Candidates should possess strong analytical skills, including data interpretation, process optimization, and problem-solving capabilities.
• Candidates should possess expertise in systems integration, including API-based integrations, data synchronization, and interoperability between business platforms.
• Candidates should possess project management skills, including planning, prioritization, timeline management, and cross-functional coordination.
• Candidates should possess team leadership skills, including mentoring, stakeholder communication, and guiding technical and non-technical team members through change.
• Candidates should possess presales and stakeholder engagement skills, including requirements gathering, solution presentation, and alignment of technology initiatives with business needs.
• Experience with business systems relevant to service or field operations (e.g., ERP, CRM, scheduling, work order and invoicing platforms) is beneficial, Aspire preferred.
• Working knowledge of data security, user access control, and compliance best practices is beneficial.
• Bachelor’s degree in Information Systems, Computer Science, Engineering, Business, or a related field, or equivalent practical experience, is preferred.
• Experience in multi-location service businesses, facilities management, landscaping, or related industries is an advantage.