System Administrator

Description

• 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