System Administrator

Job Description

Job Description

Description

The System Administrator will build and maintain the operational backbone of multiple systems and workflows across the organization’s various business entities. This role will own project execution, process documentation, and customize automation tools to creatively leverage AI to support a lean workforce. 

Minimum Qualifications

• 3-5 years managing systems at a small-to-mid sized company (professional services, agency, or SaaS)
• High degree of fluency in Notion and GoHighLevel
• Expertise using, prompting, and building workflows with AI LLMs like ChatGPT and Claude
• Comfortable building dashboards, analyzing spreadsheets, understanding data
• Background in tax, accounting, or financial services operations preferred
• Experience with intercompany or shared services structures would be ideal

Key Responsibilities

• Project Management
  • Run cross-company initiatives end-to-end: scoping, timelines, stakeholders, delivery
  • Translate leadership's strategic priorities into executable project plans with clear owners and deadlines
  • Keep multiple workstreams moving in parallel without dropping balls
  • Surface blockers early and drive resolution
• Systems Ownership (Notion, GHL, Canopy, etc.)
  • Architect and maintain our Notion workspace: databases, dashboards, SOPs, project trackers
  • Build and optimize GoHighLevel workflows, pipelines, automations, and integrations
  • Evaluate and onboard new platforms as the business needs them (Make, Zapier, Airtable, internal tools)
  • Document everything so the team can actually use what you build
• AI Integration
  • Identify workflows ripe for AI automation across client work, internal ops, and CS
  • Build and prompt-engineer AI agents, GPTs, and Claude projects for repeatable tasks
  • Stay current on LLM tooling (Claude, ChatGPT, Gemini, n8n, Zapier AI) and bring back what is useful
  • Treat AI as a force multiplier baked into every system you design, not a separate initiative
• Data & Reporting
  • Build and maintain dashboards that give leadership clear visibility into each operating company’s performance (Tax Alchemy, DMG, etc.)
  • Define the KPIs that matter for each business unit and the cadence they’re reported on (weekly scorecards, monthly business reviews, quarterly leadership decks)
  • Pull, clean, and reconcile data across platforms (Notion, GHL, QuickBooks, spreadsheets, internal tools) into a single source of truth
  • Use the right tool for the job — Google Sheets and Excel for fast iteration, BI tools (Looker Studio, Metabase, or similar) for durable reporting
  • Turn data into decisions: flag trends, surface anomalies, and bring recommendations — not just dashboards

Skills, Knowledge and Expertise

• Expert level technical skills and experience with all manner of digital platforms
• Strong ability to self-direct and use judgement when escalating bottlenecks and issues
• Comfortable diving into projects, taking initiative, and discovering (and testing) efficient solutions
• Manage a complex workload with attention to detail and competing priorities
• Handle sensitive and confidential issues with professionalism and discretion
• Communicate effectively with all levels of professionals across the organization using all manner of tools (Loom, Slack, Notion, etc.)

Benefits

• Work from home
• Medical, dental, vision, life and voluntary life insurance
• 401(k) with company match
• Paid vacation and sick days
• Paid holidays