AI Transformation Lead

Hallow • Chicago, IL

14h • $120,000 - $200,000 • Remote

About The Position

We are looking to 10x our team’s impact by becoming truly AI native in everything we do. We need someone to lead that transition by helping plan, educate, build, and integrate across the entire company.

Requirements

• Passion for the company's mission.
• Hands-on experience with AI tools, including building, debugging, and deploying real projects.
• Ability to bridge the gap between the engineering team and partner teams.
• Experience QA-ing homegrown tools at the code level.
• Understanding of backend infrastructure to build into it and explain it to non-technical teammates.
• Ability to understand and re-envision system architecture and workflows across multiple areas of an organization.
• Ability to work within the micro of specific team workflows while also building with the macro of a team-wide architecture in mind.
• Ability to earn trust and collaborate effectively with subject matter experts.
• Ability to flex training skills to teach individuals and groups across different formats and audiences, adapting teaching style and depth.
• Sensitivity to meeting each person where they are in their current personal understanding of and potential fears toward AI.
• Comfort working in ambiguity and ability to create meaningful impact in short periods of time.
• Experience building real tools, agents, and/or automations.
• Experience enabling others through learning & development, operations, program management, consulting, or transformation work.
• Ability to move fast without a playbook.

Responsibilities

• Architect the future: Embed with teams across the company to deeply map their systems, workflows, and work product, then re-envision them alongside subject matter experts - (co)designing specific solutions for each team that fit into our team-wide architecture of agents and shared knowledge bases.
• Help build the future: Build, deploy, and iterate on specialized agents and internal tools, structure & integrate data schema, and take each team through a full v1.0 workflow optimization, one team at a time. Bring others along to build with you.
• Educate & train the team: Create team resources/guides, hold office hours, and coach team members through a progressive journey from learning to creative independence. Cross-pollinate learnings and successes across the team.
• Own responsible AI use: Define and enforce how AI is used safely and responsibly, maintain internal AI and data-security policies, and run the review framework for internally built tooling.
• Coordinate our AI efforts: Lead weekly cross-functional meetings, document progress, and track adoption across every team so leadership knows what's working, what it costs, and what impact it's driving.

Benefits

• Equity compensation
• Cash compensation
• Unlimited PTO
• Insurance
• Remote-flexible work
• Fully paid parental leave
• 401(k) match
• Stipends for spiritual development, health & wellness, home-office, and learning

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed