VP of AI & Automation

VP of AI & Automation

(Executive-Track | Chief Automation Officer Path)

We are hiring a senior-level systems architect to design and lead the buildout of a modern, AI-accelerated operating backbone across our organization.

This role will function as the company’s executive owner of automation and AI infrastructure (Chief Automation Officer track), responsible for modernizing our CRM architecture, deploying intelligent automation, and embedding agentic AI into core workflows.

This is not an IT support role.

This is not a prompt-engineering role.

This is a build-first executive mandate.

The Mission

Over the next 6–12 months, you will:

• Replace fragmented systems with a clean, scalable CRM foundation (Salesforce, HubSpot, or similar)
• Architect API-first automation infrastructure (n8n or equivalent)
• Deploy AI intake parsing and CRM auto-entry workflows
• Implement RAG-based knowledge systems
• Standardize cross-department operational workflows
• Integrate marketing attribution, operational data, and financial reporting
• Reduce manual task load through intelligent automation
• Build the foundation for scalable, acquisition-ready infrastructure

What You Will Own

Enterprise Systems Architecture

• CRM selection, migration, and object modeling
• Workflow standardization across departments
• PM system implementation (ClickUp or equivalent)
• Data structure design and portability planning

Automation Backbone

• API-first system design
• Event-driven automation workflows
• Elimination of fragile tool integrations
• Automation governance and scalability

AI Infrastructure

• AI intake parsing (email, photos, field notes, claim documentation)
• Automated CRM data entry systems
• Internal AI copilots
• RAG systems over structured policy knowledge
• Vector database integration
• AI-assisted task routing and negotiation prep
• Human-in-the-loop guardrails and audit processes

Data & Reporting

• Centralized dashboards integrating operational and financial data
• Attribution and tracking stack (GA4, GTM, etc.)
• Executive reporting pipelines

Leadership

• Present architecture strategy to executive leadership
• Build and lead a technical team over time

What Success Looks Like

Within 6 Months

• CRM modernization complete or well underway
• Automation backbone deployed
• AI intake workflows operational
• Standardized processes implemented
• Reporting dashboards live

Within 12 Months

• AI copilots embedded into daily workflows
• RAG knowledge base live
• Measurable reduction in manual work
• Clean, centralized data architecture
• Systems documented and integration-ready

Required Experience

We are looking for a hybrid profile combining advanced automation engineering and AI systems architecture.

You should have:

• Experience implementing or migrating enterprise CRM platforms (HubSpot, Salesforce, etc.)
• Deep familiarity with API-driven architecture
• Hands-on automation experience (n8n, Make, Zapier at scale)
• Experience deploying LLM pipelines and RAG systems
• Experience working with vector databases
• Strong understanding of workflow modeling and system design
• Ability to translate technical architecture into executive-level strategy
• Experience building systems in ambiguous, high-growth environments

This is not a fit for:

• IT administrators
• Pure no-code consultants
• Mid-level AI engineers without architecture experience
• Prompt engineers without systems depth

Leadership Profile

You are:

• High-agency and execution-driven
• Direct and intellectually honest
• Comfortable challenging leadership constructively
• Strong cross-functional communicator
• Experimental but disciplined
• Motivated by building leverage, not maintaining status quo

Compensation

• Base Salary: $190,000–$220,000
• Performance incentives tied to operational milestones.
• Options for right candidate

Why This Role Matters

We are building a scalable, AI-accelerated operating system that will:

• Increase margin
• Reduce manual labor dependency
• Standardize workflows
• Create defensible, tech-enabled differentiation
• Strengthen enterprise valuation

If you can ship quickly without building fragility and want to architect real enterprise leverage we want to speak with you.

Pay: $180,000.00 - $240,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Flexible schedule
• Health insurance
• Paid time off
• Vision insurance

Work Location: In person