Remote AI Transformation Lead

Drive Capital; Chicago (IL); On-site; USD 120,000 - 200,000; Full time

Job summary

Hallow is seeking an AI Transformation Lead to guide the company through a full AI-native transition. You will embed with teams, map workflows, and design agent-based solutions that scale across the organization. This is a hands-on role bridging engineering and product, with a focus on safe and responsible AI use.

Location is flexible within the U.S.; Chicago HQ preferred but remote work is supported. The role offers equity, competitive cash compensation, and a top-tier benefits package as part

Responsibilities

• Architect the future by embedding with teams to map systems and workflows, and co-design solutions for each team within our agent-based architecture.
• Build, deploy, and iterate on specialized agents and internal tools; structure data schema and guide each team through a v1.0 workflow optimization.
• Lead education and training, create guides, hold office hours, coach team members toward independent creativity.
• Own responsible AI use by defining and enforcing safe practices, maintaining AI and data-security policies, and running a review framework.
• Coordinate AI efforts by leading weekly cross-functional meetings, documenting progress, and tracking adoption and impact.

Job description

Hallow is seeking an AI Transformation Lead to guide the company through a full AI-native transition. You will embed with teams, map workflows, and design agent-based solutions that scale across the organization. This is a hands-on role bridging engineering and product, with a focus on safe and responsible AI use.

Location is flexible within the U.S.; Chicago HQ preferred but remote work is supported. The role offers equity, competitive cash compensation, and a top-tier benefits package as part