Sr. Director - AI, Innovation and Digital Employee Experience (AI)

TL;DR

Sr. Director - AI, Innovation and Digital Employee Experience (AI): Defining and driving the multi-year AI and automation strategy for the digital employee experience with an accent on integrating LLMs, productivity tools, and identity systems. Focus on architecting an integrated employee experience layer, reimagining operating models to embrace AI, and building KPI frameworks for AI-driven productivity.

Location: United States - Illinois - Chicago (Flexible work model)

Salary: $244,500 – $342,000

Company

hirify.global powers global travel through cutting-edge technology and AI-driven experiences.

What you will do

• Define and own the holistic digital employee experience vision across the entire employee lifecycle.
• Drive the multi-year AI and automation strategy for Collaboration, Productivity, and Corporate IT.
• Architect the integrated employee experience layer connecting platforms like Workday, ServiceNow, Glean, and Slack.
• Reimagine team structures and operating models to embed AI as a core capability.
• Build KPI frameworks to measure adoption, time saved, and AI-driven productivity gains.
• Align priorities and governance across IT, HR, Finance, Security, and Engineering.

Requirements

• Must be based in the USA (Chicago location).
• 12+ years of experience in technology, product, or AI/ML platform roles.
• Proven track record of leading enterprise-scale internal platforms or digital workplace solutions.
• Deep technical fluency in LLM integration, API design, and workflow automation.
• Experience driving AI agendas and shipping AI-powered products.
• Strong ability to influence senior stakeholders and build AI-fluent teams.

Nice to have

• Advanced degree in Computer Science, Engineering, or Data Science.
• Experience operating global-scale AI-powered digital workplace platforms.
• Leadership in defining technical standards for AI-enhanced internal tools.
• Familiarity with agentic workflows and generative AI integration at enterprise scale.

Culture & Benefits

• Full benefits package including medical, dental, and vision insurance.
• Generous time-off and parental leave.
• Wellness and travel reimbursements, travel discounts, and IATAN membership.
• Flexible work model with modern office spaces.
• Career development resources and a culture of belonging and inclusivity.