ClassWallet

Director, AI – Automation

ClassWallet

full-time

Posted on:

Location Type: Remote

Location: United States

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Job Level

Lead

Tech Stack

RPA

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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.

Requirements

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

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
AIautomationmachine learningRPAdata-driven initiativesproject managementchange managementadult learning methodologiesAI governancedata privacy standards
Soft Skills
coachingcommunicationstakeholder managementleadershipteam collaborationstrategic thinkingproblem-solvingadaptabilitymentoringcontinuous improvement
Certifications
advanced degree in engineeringadvanced degree in computer science