Director, AI & Automation

ClassWallet, a leading financial technology company in the United States, is seeking to hire a Director, AI & Automation to join our team.

ClassWallet is a financial technology company serving agencies delegated responsibility to manage public funds. Agencies use ClassWallet to get public funds to the right people, and ensure the funds are used for the right purpose. ClassWallet’s suite of products and services empowers agency administrators to dramatically increase efficiency of funds distribution and spend compliance, reduce programmatic costs, maximize the full potential impact of the program, and satisfy the needs and expectations of policymakers, constituents and public reporting. ClassWallet has processed over $3.5 Billion to date and serves public agencies across 33 states.

The Company has developed an industry-defining digital wallet solution which has gained rapid traction among state and local agencies and school districts across America. ClassWallet ranks as the 61st fastest growing software company on the prestigious Inc. 5000 list of fastest-growing private companies and the 21st fastest growing financial technology company on the Deloitte Technology Fast 500 in 2023.

While the Company delivers immense business value, the social impact of ClassWallet is a fabric that runs through its mission and corporate culture. As a result of ClassWallet’s innovation, public programs run with exponentially more efficiency and the impact and breadth of the programs for the individuals they serve is dramatically higher. This mission compliments the Company mission-based culture with focus on gratitude and work-life balance.

About the Role

The Director, AI & Automation is a strategic and hands-on leadership role responsible for driving the adoption and integration of artificial intelligence and automation technologies across the organization. Reporting directly to the VP, Product & Engineering, this individual will lead the company's AI transformation agenda — working side-by-side with teams and individuals to get them moving quickly, accelerating how work gets done, increasing the volume and quality of output, and significantly reducing operational costs.

This is not a purely strategic role. The right candidate rolls up their sleeves, embeds with teams, and acts as a personal AI coach, accelerator, and implementation partner across the business.

Responsibilities

Hands-On Team & Individual Enablement

• Actively embed with departments, teams, and individuals to help them adopt AI tools in their day-to-day work
• Run working sessions, workshops, and 1:1 coaching to rapidly upskill employees at all levels
• Identify quick wins within each group and help implement them fast — building momentum and confidence
• Build AI tools and agents as needed to help accelerate organizational adoption and use
• Act as a go-to resource for anyone in the company looking to leverage AI in a new way
• Create a "first mover" culture by celebrating early adopters and sharing wins company-wide

AI Strategy & Roadmap

• Develop and execute a company-wide AI and automation strategy aligned with business objectives
• Identify high-impact opportunities to embed AI across all departments and functions
• Build and maintain a prioritized roadmap of AI initiatives with measurable ROI

Execution & Delivery

• Lead cross-functional teams to implement AI tools, workflows, and platforms
• Partner with department heads to redesign processes using AI and automation
• Oversee vendor selection, procurement, and management of AI technologies

Performance & Cost Optimization

• Establish KPIs to measure the impact of AI adoption on productivity, output volume, and cost reduction
• Report progress and outcomes directly to the CEO and executive leadership team
• Drive continuous improvement cycles based on data and performance feedback

Culture & Change Leadership

• Champion an AI-first mindset across the organization — starting with people, not technology
• Make AI approachable and practical for non-technical employees
• Remove barriers to adoption by simplifying tools, creating guides, and offering ongoing support
• Develop scalable training programs that get people productive with AI quickly

Governance & Risk

• Work with Legal/Compliance to establish AI governance policies, ethical guidelines, and data privacy standards that are in compliance with relevant regulations and responsible AI practices 
• Ensure compliance with relevant regulations and responsible AI practices responsible deployment of automated systems in alignment with the above

Required:

• 8+ years of experience in technology, operations, or digital transformation roles
• 3+ years leading AI, automation, or data-driven initiatives at scale
• Deep knowledge of AI/ML tools, LLMs, RPA, and automation platforms (e.g., UiPath, Zapier, Microsoft Copilot, OpenAI, Claude, etc.)
• Proven track record of getting teams and individuals to rapidly adopt new technology
• A natural coach and communicator — equally comfortable with executives and frontline employees
• Proven track record of delivering measurable cost savings and efficiency gains
• Project management skills
• Strong executive communication and stakeholder management skills

Preferred:

• Experience as an embedded AI champion or transformation lead within a technology company
• Background in product, engineering, data science, or operations
• Familiarity with change management and adult learning methodologies
• Advanced degree in a relevant field such as engineering or computer science

ClassWallet is a positive, family-oriented team environment. Our focus is on encouragement, positive reinforcement, and gratitude. We work hard and are highly motivated to win but with a healthy perspective on life.

We offer an excellent salary and benefits commensurate with experience.

ClassWallet.com is proud to be an Equal Opportunity Employer. Applicants are considered for all positions without regard to race, color, religion, sex, national origin, age, disability, sexual orientation, marital or veteran status.