Director, AI Enablement and Innovation (Annapolis)

Why UKG:

At UKG, the work you do matters. The code you ship, the decisions you make, and the care you show a customer all add up to real impact. Today, tens of millions of workers start and end their days with our workforce operating platform. Helping people get paid, grow in their careers, and shape the future of their industries. That’s what we do.

We never stop learning. We never stop challenging the norm. We push for better, and we celebrate the wins along the way. Here, you’ll get flexibility that’s real, benefits you can count on, and a team that succeeds together. Because at UKG, your work matters—and so do you.

About the Role:

Lead innovation and knowledge strategy for CX (Customer Experience) Learning & Enablement by defining knowledge architecture, implementing AI and workflow intelligence solutions, and driving automation across the content lifecycle. Combine product, data and learning expertise to deliver modern, searchable, and integrated knowledge experiences that reduce friction for learners, support agents and partners.

Core Responsibilities:

• Define and own the knowledge architecture and taxonomy strategy for CX learning and enablement content (including canonical content models, metadata standards, and governance).

• Design and implement generative AI/RAG solutions, intelligent search, conversational assistants, and contextual learning surfaces that integrate with product workflows and frontline tools.

• Own strategy and execution for content lifecycle automation and integrations (CMS LMS KM product docs translation pipelines), improving authoring, review, and publishing velocity.

• Act as technical product owner for integrations and tooling (content APIs, search, knowledge base platforms, LLM infra), coordinate with Product Engineering and P&E for secure, scalable deployments.

• Drive experimentation and pilot programs to validate AI/automation use cases (e.g., auto-summary, auto-tagging, content recommendations, test generation). Evaluate vendors and open-source approaches; manage POC lifecycle.

• Implement measurement frameworks for knowledge efficacy: search success, answer relevance, RAG precision/recall, content reuse, time to publish, and impact on case deflection and support outcomes.

• Build data governance practices for content/AI (bias, privacy, provenance, feedback loops).

• Collaborate with Curriculum Development, Learning Business Partners, Adoption & Value, and Support to ensure innovation projects map to clear business outcomes.

Basic Qualifications:

• 8+ years’ experience in knowledge management, product/technical program management, or AI/data product roles with at least 3+ years leading teams or programs.

• Practical experience deploying enterprise AI/search/KM solutions (LLM/RAG, vector search, knowledge graphs, conversational AI) and implementing integrations between LMS/CMS/KM systems.

• Strong technical literacy: APIs, data modeling, metadata/taxonomy design, and vendor evaluation for AI/KM tooling.

• Experience working with engineering/product teams to bring technical solutions to production.

Preferred Qualifications:

• Bachelor’s degree in technical field, information science, or equivalent experience.

• Hands-on experience with LLMs, vector databases, RAG approaches, and tools

• Experience in SaaS/HR tech or with support and digital adoption use cases.

• Familiarity with content localization pipelines and enterprise taxonomy management.

• Advanced degree in information science, AI, or related field.

Competencies:

Technical product leadership, innovation & experimentation, systems thinking, data-driven decision making, stakeholder influence across technical and non-technical partners, risk and governance orientation.

Company Overview:

UKG is the Workforce Operating Platform that puts workforce understanding to work. With the world's largest collection of workforce insights, and people-first AI, our ability to reveal unseen ways to build trust, amplify productivity, and empower talent, is unmatched. It's this expertise that equips our customers with the intelligence to solve any challenge in any industry — because great organizations know their workforce is their competitive edge. Learn more at ukg.com.

Equal Opportunity Employer:

UKG is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, disability, religion, sex, age, national origin, veteran status, genetic information, and other legally protected categories.

View The EEO Know Your Rights poster (

UKG participates in E-Verify. View the E-Verify posters here ( .

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Disability Accommodation in the Application and Interview Process:

For individuals with disabilities that need additional assistance at any point in the application and interview process, please email View email address on apply.placed-app.com .

The pay range for this position is $129,500 to $186,100. The actual base pay offered may vary depending on skills, experience, job-related knowledge and work location. In addition to base pay, employees may be eligible to participate in a performance-based bonus plan and to receive restricted stock unit awards as part of total compensation. Learn more about UKG’s benefits and rewards at

It is the policy of Ultimate Software to promote and assure equal employment opportunity for all current and prospective Peeps without regard to race, color, religion, sex, age, disability, marital status, familial status, sexual orientation, pregnancy, genetic information, gender identity, gender expression, national origin, ancestry, citizenship status, veteran status, and any other legally protected status entitled to protection under federal, state, or local anti-discrimination laws. This policy governs all matters related to recruitment, advertising, and initial selection of employment. It shall also apply to all other aspects of employment, including, but not limited to, compensation, promotion, demotion, transfer, lay-offs, terminations, leave of absence, and training opportunities.