Head of AI & Automation

CASH DEPOT LTD•Green Bay, WI
•$100,000 - $120,000•Onsite

About The Position

The Head of AI & Automation turns business opportunities into practical, measurable improvements through AI and automation. Working across every Cash Depot department, this role identifies valuable use cases, evaluates tools, leads pilots, drives adoption, and verifies results. The position combines business process analysis, technical judgment, and change leadership. Reporting directly to the Chief Technology Officer, the Head of AI & Automation partners with Engineering, IT Operations, Security and Compliance, HR, and department AI champions. The role builds and manages a prioritized portfolio of AI and automation initiatives tied to business goals, evaluates tools and vendors, leads prototypes and pilots, supports adoption and training, and maintains governance and reporting for approved use cases.

Requirements

  • Demonstrated delivery of business process improvements using AI or automation, with measurable outcomes and sustained adoption.
  • Practical understanding of AI capabilities and limits, data quality, evaluation, access controls, APIs, enterprise integration, and vendor assessment.
  • Ability to guide or build prototypes using scripting, APIs, or automation tools and work credibly with engineering specialists.
  • Experience managing several initiatives at once, from decision through implementation.
  • Relevant education or equivalent experience.
  • Strong discovery, process analysis, and prioritization skills.
  • Proven stakeholder management and change leadership across business functions.
  • Ability to explain tradeoffs clearly to executives, department leaders, and employees.
  • Skill at setting meaningful measures and proving results with data.
  • Ability to balance big-picture vision with hands-on execution.
  • Collaborative leadership that builds trust and influence without direct authority.
  • Passion for innovation and practical, responsible use of AI.

Nice To Haves

  • Experience in regulated financial services, payments, or the ATM industry.
  • Experience with internal knowledge tools, document processing, workflow automation, and distributed development teams.

Responsibilities

  • Build and maintain a prioritized AI and automation portfolio aligned with business goals, owners, expected benefits, costs, and delivery capacity.
  • Analyze workflows with department leaders and employees and recommend AI, conventional automation, or process changes as appropriate.
  • Evaluate vendors and tools for capability, integration, data handling, cost, and supportability alongside Engineering and Security and Compliance.
  • Define pilot scope, baselines, acceptance criteria, evaluation methods, human review needs, and scale-or-stop recommendations.
  • Lead prototypes and pilots with technical resources, then hand them off to Engineering and Operations owners before production.
  • Organize department champions, training, guidance, and employee feedback with HR and business owners.
  • Track adoption and the benefits delivered by each initiative.
  • Maintain an inventory of approved AI use cases and tools, including owners and review status.
  • Prepare decisions for the monthly AI steering group.
  • Report progress, costs, accuracy, adoption, benefits, and risks to the CTO.

Benefits

  • Competitive compensation package
  • Profit sharing
  • Bonus program
  • Comprehensive medical, dental, and vision benefits
  • Company-paid life insurance
  • Company-paid short-term disability
  • 401(k) with company match
  • Paid time off and holidays
  • Direct partnership with the CTO and department leaders
  • Opportunity to build the company's AI and automation program
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