Head of Digital Innovation and AI Automation

About the Role

A privately held group of operating companies operating across distribution, automotive rental, towing and parking management, and field-service industries is seeking a Head of Digital Innovation and AI Automation to establish, run, continuously maintain, and improve an internal AI agency serving four operating companies.

The central mandate is to build and sustain a portfolio of approximately 10 production AI agents for each company about 40 agents across the group that improve revenue, margins, productivity, customer experience, management control, and decision-making.

This is a hands-on builder-operator role, not a strategy-only or prompt-engineering position.

The successful candidate will report directly to the CEO and ownership, personally lead architecture and delivery, work with operating teams to redesign workflows, and manage internal or external technical resources as the agency grows.

Each agent must have an approved business purpose, defined owner, secure access, human oversight, measurable performance, and a clear return on investment.

Deep Philosophy for AI Adoption

A defining requirement of this position is a deep philosophical belief and practical approach for helping others throughout the group embrace AI.

The leader must understand that lasting adoption cannot be achieved through mandates, technical demonstrations, or hype.

It is earned through trust, transparency, employee participation, practical education, respect for legitimate concerns, visible early wins, and honest communication about both the capabilities and limitations of AI. The leader must help employees see AI as a partner that expands human capability, improves the quality of their work, and removes repetitive tasks while preserving human judgment, dignity, and accountability.

Key Responsibilities

• Build and Run the Internal AI Agency: Create and permanently operate the agency operating model, technical standards, intake process, delivery methodology, staffing plan, vendor structure, budget, documentation standards, support coverage, and executive reporting needed to serve all four companies.
• AI Agent Portfolio: Develop a prioritized portfolio of approximately 10 production agents per company. Sequence delivery according to business value, data readiness, risk, integration effort, and employee capacity rather than deploying agents solely to meet a numerical target.
• Hands-On Agent Development: Design, build, test, and deploy agentic workflows using large language models, APIs, databases, retrieval systems, automation platforms, and appropriate orchestration tools. Build directly while also setting standards for other developers.
• Business Process Discovery: Work inside each operation to map workflows, identify repetitive work and control gaps, define the human and agent responsibilities, and convert business requirements into reliable production solutions.
• Systems Integration: Integrate agents with Odoo, TSD, TowCentric, Housecall Pro, websites, apps, email, messaging, document repositories, telephony, databases, and other approved systems while minimizing duplicate entry and fragmented data.
• Agent Governance and Lifecycle Management: Establish development, testing, approval, deployment, versioning, monitoring, incident response, rollback, and retirement procedures. Maintain an inventory showing every agent's purpose, owner, permissions, dependencies, cost, and current status.
• Security, Privacy, and Human Oversight: Apply least-privilege access, protect sensitive customer, employee, payment, vehicle, property, and commercial data, and require human approval for high-risk decisions or external actions. Coordinate independent security review when appropriate.
• Performance and ROI: Define service levels and evaluation methods for accuracy, reliability, response time, adoption, cost, time saved, revenue contribution, error reduction, and financial return. Promptly correct, restrict, or retire agents that fail established standards.
• Continuous Maintenance and Improvement: Continuously monitor and improve the agency and every deployed agent.

Maintain integrations, prompts, tools, knowledge sources, models, infrastructure, permissions, evaluations, documentation, and training as business processes and technology change.

Regularly retest performance, correct degradation, reduce cost and latency, add capabilities, and upgrade or replace components when justified.

• Team and Vendor Leadership: Recruit or direct developers, automation specialists, data resources, and outside vendors as needed. Own technical decisions, code and documentation quality, delivery schedules, budgets, and vendor accountability.
• Adoption and Change Leadership: Train employees, document new workflows, assign business owners, measure usage, and address resistance or workarounds so each deployed agent becomes part of the operating process.

Qualifications

• Production AI Agent Experience: Demonstrated responsibility for designing, building, deploying, and operating production AI agents or complex agentic workflows. General ChatGPT use, prompt writing, prototypes, or advisory experience alone is not sufficient.
• Technical Capability: Hands-on proficiency with Python, SQL, APIs, large language models, tool calling, retrieval-augmented generation, vector databases, agent orchestration, workflow automation, evaluation, observability, authentication, and cloud deployment.
• Agency or Team Leadership: Experience leading an AI automation agency, AI center of excellence, product engineering group, or comparable delivery organization with responsibility for staffing, standards, budget, quality, and results.
• Enterprise Systems: Demonstrated ability to improve ERP, CRM, fleet, dispatch, field-service, e-commerce, or other operational platforms. Experience with Odoo, TSD, TowCentric, or Housecall Pro is helpful but not required.
• Business Acumen: Ability to understand P&L drivers and frontline workflows, quantify expected benefits, prioritize competing needs, and translate operational problems into solutions employees can use.
• Responsible Delivery: A record of secure deployment, structured testing, human-in-the-loop controls, monitoring, documentation, incident handling, and measurable post-launch performance.
• Leadership and Communication: Strong executive communication and the ability to earn trust with managers and frontline employees, challenge assumptions constructively, and drive adoption without unnecessary complexity.
• Philosophy of Human Adoption: A clear point of view on how people accept technological change, supported by examples of overcoming skepticism, fear, poor adoption, or resistance to AI and automation.
• Education: Bachelor's degree in computer science, information systems, engineering, data science, business, or a related discipline, or equivalent professional experience.

Success Measures

• First 90 days: Complete a business-process, systems, data, security, and vendor assessment for all four companies; establish the AI agency operating model; identify candidate agents; and present a prioritized portfolio with business owners, budgets, dependencies, risks, and expected returns.
• First six months: Put the shared architecture, governance, monitoring, documentation, and support model into operation and deploy the first high-value production agents in each company with measured adoption and performance.
• First 12 to 18 months: Build and operationalize approximately 10 approved production AI agents for each company - about 40 across the group - while meeting defined standards for security, reliability, human oversight, adoption, and return on investment.
• Business impact: Produce verified improvement in revenue conversion, gross margin, labor productivity, fleet utilization, scheduling, inventory accuracy, customer response time, error reduction, compliance, or another approved operating KPI.
• Ongoing operation: Maintain the agency permanently through an up-to-date agent registry, scorecards, access and cost reviews, maintenance records, and quarterly improvement recommendations.

Salary: $120,000 to $150,000 per year