Assistant Vice President, AI-Driven Transformation

Hirewell; Chicago, Northern (IL, KY); Hybrid; USD 95,000 - 150,000; Full time

Job summary

Hirewell in Chicago, IL seeks an Assistant Vice President to drive AI-enabled business transformation across the firm. This is not a software role but a business partner role, collaborating with stakeholders to redesign workflows and operating models with AI at the core.

You’ll work across investment, investor relations, and back-office domains, shaping end-to-end processes from origination to execution. You’ll lead workshops, build ROI models, and develop scalable transformation playbooks while

Qualifications

• Bachelor’s degree in computer science, business, or related field.
• 5+ years in business process transformation, process reengineering, management consulting, or strategic technology consulting.
• Demonstrated experience leading operating model redesign or transformation initiatives.
• Foundational understanding of modern AI capabilities (agentic systems, RAG, knowledge-grounding frameworks).
• Experience building cost models, ROI/TCO analyses, and business cases.
• Strong facilitation skills; comfortable leading workshops with audiences from front-line staff to senior leadership.
• Excellent communication skills; translate technical possibilities into executive terms.
• Python familiarity is a plus.

Responsibilities

• Partner with business leaders to identify, prioritize, and roadmap AI transformation opportunities.
• Conduct current-state and future-state assessments, redesigning processes using AI-first design principles.
• Lead workshops and discovery sessions with stakeholders from front-line to executives.
• Build business cases, ROI models, and value realization frameworks for executive buy-in.
• Collaborate with engineering and delivery teams to translate designs into roadmaps.
• Develop reusable transformation frameworks and playbooks that scale across the firm.
• Evaluate emerging AI capabilities and translate them into practical business applications.

Skills

Facilitation

Communication

Python familiarity

Education

Bachelor’s degree in computer science, business, or related field

Job description

Hirewell in Chicago, IL seeks an Assistant Vice President to drive AI-enabled business transformation across the firm. This is not a software role but a business partner role, collaborating with stakeholders to redesign workflows and operating models with AI at the core.

You’ll work across investment, investor relations, and back-office domains, shaping end-to-end processes from origination to execution. You’ll lead workshops, build ROI models, and develop scalable transformation playbooks while