Systems & Office Manager

We are seeking a dynamic Systems & Office Manager to oversee our administrative operations, office systems, and team coordination. This vital role combines office management, vendor relations, human resources, and basic financial tasks to keep our organization running smoothly. The ideal candidate will be energetic, highly organized, and proactive in managing multiple responsibilities to support our growing team., 1 | Systems Ownership & Implementation (40% of role)

• Own the Aspire operating system - configuration, templates, user access, module rollout, and ongoing optimization
• Build and maintain Aspire reporting dashboards that give CEO and leadership real-time visibility across all divisions and entities
• Manage HubSpot CRM - pipelines, automations, deal stage workflows, and integration with Aspire
• Administer RealGreen / WorkWave for recurring green service routes and fertilization tracking
• Oversee GPS fleet tracking platforms (Samsara or Verizon Connect) - data integrity, alert configuration, and utilization reporting
• Identify and deploy AI tools (Claude, ChatGPT, automation platforms) to eliminate repetitive manual workflows across the business
• Serve as the internal Aspire Administrator - the primary resource for staff training, troubleshooting, and system evolution
• Build and maintain the Zapier / API automation layer connecting Aspire, HubSpot, Sage Intacct, and other platforms

2 | Reporting & Cross-Entity Visibility (30% of role)

• Design and produce a weekly leadership dashboard - KPIs across all divisions, entities, and seasons
• Build monthly operational reporting packages for CEO: revenue by division, job cost actuals vs. budget, fleet utilization, and headcount
• Create snow-season event reporting - service tickets, GPS timestamps, salter records, and client documentation for liability protection
• Develop sales pipeline reporting across all 5 Aspire pipelines - close rates, bid volume, rep performance
• Track and report on AI/automation ROI - hours saved, errors eliminated, workflow improvements quantified
• Coordinate with CFO on Aspire-to-Sage Intacct data flow and monthly close accuracy

3 | Office & Admin Team Management (30% of role)

• Directly supervise Customer Service Reps (×2), Office/Admin Coordinator, and Dispatch support staff
• Set and enforce office procedures, communication standards, and response time expectations across all brands
• Manage inbound client communication workflows - routing, escalation, and documentation in Aspire CRM
• Oversee scheduling and dispatching support function during green season
• Conduct regular 1:1s, performance reviews, and development planning for direct reports
• Manage office supply procurement, vendor relationships, and facilities coordination
• Support HR with onboarding workflows and system access provisioning for new hires

Do you have experience in User training (technical support)?, Required

• 3-5 years in an operations, systems, or office management role
• Demonstrated experience administering or implementing field service / operations software
• Proven ability to build reports and dashboards that non-technical leaders can use
• Experience supervising an admin or customer service team
• Comfortable learning new software quickly and training others on it
• Strong organizational discipline - manages multiple systems and deadlines simultaneously
• Proficient in Microsoft 365 - Excel, Teams, SharePoint
• Experience with CRM platforms and workflow automation tools

Preferred

• Background in landscape, field services, construction, or trades
• Hands-on experience with Aspire, LMN, RealGreen, or similar landscape platforms
• Familiarity with Sage Intacct or comparable multi-entity accounting systems
• Experience deploying AI tools (Claude, ChatGPT, Zapier AI) in a business setting
• GPS fleet management platform experience
• Exposure to seasonal business operations - staffing swings, event-based workflows
• Nonprofit or multi-entity business experience a plus

Join us to lead our office operations with enthusiasm and precision! This role offers an exciting opportunity to support a thriving organization dedicated to excellence in landscape services while fostering a collaborative team environment.

Pulled from the full job description

• 401(k)
• Health insurance
• Paid time off
• Vision insurance
• Dental insurance
• Flexible spending account
• Life insurance, * 401(k)
• Dental insurance
• Flexible spending account
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Troy Clogg Landscape Associates is a $20-30M multi-entity field services organization operating across snow and ice management, landscape construction, lawn care, tree care, irrigation, and landscape supply. As the company scales and transitions into Aspire as its primary operating system, we are creating a dedicated Systems & Office Manager role to own the technology infrastructure, drive cross-entity reporting visibility, and manage the administrative team. This is not a traditional office manager role. Roughly 70% of this position lives in systems, software, automation, and data - the remaining 30% involves supervising admin and customer service staff. The right person will be as comfortable building a reporting dashboard in Aspire as they are running a team meeting or troubleshooting a HubSpot workflow.