AI Executive Assistant

Job Summary

The AI Executive Assistant will serve as the technical engine behind the firm's operational automation roadmap. This role coordinates multi-platform software connections (Make.com, Zapier, n8n) and builds custom AI agents (via Claude Projects, OpenAI Custom GPTs). It also bridges operational fields to sync real-time data flows between Procore and HubSpot while engineering an automated inbox triage system for leadership.

Qualification

• Linguistic Fluency: Complete, native-level written and verbal English communication skills, with a proven ability to translate complex business challenges into precise technical integration blueprints.
• Autonomous Operating Style: Exceptional capability to build systems from scratch with minimal management direction, exhibiting strong judgment on when to deploy an integration versus when to iterate.
• Discretion & Trustworthiness: Absolute professionalism and ethical boundary management as the role transitions into high-level executive schedules, financial receipt tracking, and corporate strategy discussions.

Experience

Candidates must exhibit an established background in modern workflow orchestration and systems management:

Workflow Automation & AI Agent Engineering

• On-the-Job Tenure: Minimum of three (3) or more years of professional experience in a role dedicated to workflow automation, AI infrastructure management, business operations, or high-tier technical executive support.
• Middleware Integration Footprint: Proven, hands-on history building complex multi-step pipelines within at least two of the following platforms: Zapier, Make.com, or n8n.
• LLM Production Deployments: Documented experience building functional AI agents, automated summary loops, or custom workspaces utilizing Claude Projects, OpenAI Custom GPTs, or related LLM orchestration layers, backed by strong, production-grade prompt engineering skills.
• Scheduled Data Architecture: Direct experience configuring automated cron-jobs, scheduled digests, cross-platform triggers, webhooks, and reporting syncs.

Enterprise SaaS & Domain Literacy (Preferred)

• Construction Ecosystem Exposure: Foundational experience working with Procore or equivalent construction management frameworks (such as Autodesk Construction Cloud, PlanGrid, or Buildertrend) within the AEC, real estate, or industrial project sectors is highly preferred.
• CRM & Workspace Management: Working operational knowledge of HubSpot (including properties, custom objects, and workflow engines) and the Microsoft 365 suite (Outlook, Teams, SharePoint).
• Extensible Scripting Foundation: Foundational familiarity with relational database backbones like Airtable, Notion, or Coda, supplemented by light scripting capability (JavaScript or Python) to extend no-code middleware limits, is a distinct advantage.
• Executive Coordination: Past experience acting as a technical Executive Assistant, Virtual Assistant, or Chief of Staff assisting C-suite or VP-level corporate leaders.

Key Responsibilities

AI Systems Architecture, Workflow Engineering & Middleware Integration

• Architect Multi-SaaS Pipelines: Design, build, and optimize end-to-end automations, custom tracking dashboards, and data connections across HubSpot, Microsoft 365, Procore, Make.com, Zapier, and n8n.
• Deploy Custom AI Agents: Construct and maintain operational AI agents using Claude Projects and ChatGPT architecture to automate documentation parsing, summarize logs, and reduce manual entry.
• Build Scheduled Reporting Engines: Launch automated, scheduled processes for real-time construction reporting, project compliance audits, and strategic metric summaries.
• Bridge Construction & Sales Systems: Connect Procore with HubSpot and internal communication nodes to ensure project data flows seamlessly across field operations and executive dashboards.
• Maintain System Documentation: Keep technical blueprints, prompt libraries, workflow logic maps, and Standard Operating Procedures (SOPs) continually updated to ensure system continuity.

Automated Communication & Phased Executive Support

• Automate Inbox Triage: Engineer advanced inbox filtering frameworks, including AI-generated email drafts, context-aware routing rules, and automated leadership briefings.
• Coordinate Strategic Schedules: Transition into hybrid executive support duties over time, managing calendars, organizing operational reminders, and maintaining expense tracking systems.
• Manage Executive Travel: Coordinate travel logistics, build itineraries, compile background briefing files, and prepare clear meeting agendas for the VP of Operations.
• Pilot Frontier AI Software: Evaluate emerging AI tools, run software pilots, and recommend updates to ensure the firm's automation stack remains cutting-edge.

Skills Required:

• Computer / Software / It / Data