Jobs › Options Clearing Corporation

Principal, AI Enablement & Change

Options Clearing Corporation · Chicago, IL · $167,800–$226,400 a year · Full time

Posted Sep 21, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a change management effort you led where people were resistant. What worked?

What they are checking: Real experience driving adoption against skepticism or fear, which AI often triggers.

How do you talk with employees who worry AI will replace their jobs?

What they are checking: Honest, calm communication that builds trust without making promises the firm has not made.

Tell me about a time you influenced senior leaders without direct authority.

What they are checking: Executive influence, which an enterprise-wide change role depends on.

What would you do

An AI tool is delivered but usage is low after three months. How do you figure out why?

What they are checking: Diagnosing adoption problems through user research and data rather than adding more training by default.

How would you work with business leaders to redesign roles as AI is built into their work?

What they are checking: Workforce transformation skill and sensitivity to employee concerns about job change.

How would you split responsibility for adoption between you and the AI Solutions Leads who own individual use cases?

What they are checking: Clarity about enterprise versus use-case accountability so efforts do not overlap or leave gaps.

In a regulated clearinghouse, how do you encourage AI use while making sure people follow the AI Policy?

What they are checking: Balancing enthusiasm and guardrails so adoption does not create compliance risk.

About the work

How would you design an AI literacy program that reaches every AI user at OCC on hire and at least yearly?

What they are checking: Program design that scales across roles while meeting the requirements of the firm's AI Policy.

What does role-appropriate AI training look like for a risk analyst versus an executive versus an engineer?

What they are checking: Ability to tailor learning to how each group actually uses AI and the risks they face.

What metrics would tell you that AI adoption at OCC is real and responsible?

What they are checking: Measurement thinking that goes beyond logins to value, quality and risk.

Practice this interview out loud.

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The full job description

As published by Options Clearing Corporation.

To be considered for this position, applications and resumes are accepted only through our careers site by directly applying to the posted job. We do not accept unsolicited resumes or sales solicitations from staffing agencies. Any OCC employee wishing to submit a referral must do so through their Workday account. Any resume submitted outside of an active job posting will not be considered for employment. What You'll Do: The Principal, AI Enablement & Change owns the organizational adoption of AI at OCC — the AI literacy program, the workforce transformation agenda, and the change management that determines whether AI capabilities delivered through the use case pipeline actually get used. This role complements the AI Solutions Leads, who are accountable for adoption within individual use cases, by owning the enterprise-wide dimension of adoption across OCC. Primary Duties and Responsibilities: To perform this job successfully, an individual must be able to perform each primary duty satisfactorily. • Own and evolve OCC's enterprise AI literacy program, ensuring role-appropriate AI training reaches all users of AI at OCC on hire and at least annually thereafter, consistent with the Artificial Intelligence Policy. • Lead the workforce transformation agenda associated with AI adoption, partnering with business functions to redesign roles as AI is embedded into how work gets done. • Design and drive change management programs for individual AI use cases as they move from production into broad adoption, working in coordination with the AI Solutions Leads who own use case delivery. • Identify and address adoption friction, resistance, and AI literacy gaps at the enterprise level before they surface as recurring, use-case-level failures. • Develop and track adoption metrics (e.g., embedded/recurrent AI use by role and function) and report progress against OCC's AI Strategy adoption targets. • Partner with AI Portfolio & Transformation (AIPT) to align enablement and change activities with the AI roadmap and the pace of the use case pipeline reaching production. • Build change management playbooks and communication materials that can be reused across use cases and business functions. • Serve as a point of connection between the business, AIPT, and AIRE on questions of adoption readiness and organizational impact. Supervisory Responsibilities: None at this time. May coordinate cross-functional working sessions and matrixed contributors supporting specific enablement initiatives, without direct reporting authority. Qualifications: The requirements listed are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the primary functions. • Demonstrated experience leading organizational change management programs, ideally tied to technology adoption or digital transformation. • Working knowledge of AI/GenAI tools and their practical use in a corporate environment; ability to speak credibly to both business and technical audiences about adoption. • Experience designing and delivering enterprise training or literacy programs. • Proficiency in developing adoption metrics, reporting frameworks, and executive-level status communication. • Strong facilitation skills; ability to run workshops and working sessions across business and technology stakeholders. • Microsoft Office Suite; familiarity with process/workflow documentation a plus. Technical Skills: • None Education and/or Experience: • Bachelor's degree in a relevant field, or equivalent experience. • 10+ years of experience in change management, organizational transformation, learning & development, or a related discipline. • Prior experience supporting an enterprise technology rollout (AI, automation, or major systems implementation) strongly preferred. • Experience operating in a regulated or financial services environment preferred, given OCC's role as a Systemically Important Financial Market Utility (SIFMU). Certificates or Licenses: • N/A — relevant AI product management, project management, or domain certification is a plus About Us The Options Clearing Corporation (OCC) is the world's largest equity derivatives clearing organization. Founded in 1973, OCC is dedicated to promoting stability and market integrity by delivering clearing and settlement services for options, futures and securities lending transactions. As a Systemically Important Financial Market Utility (SIFMU), OCC operates under the jurisdiction of the U.S. Securities and Exchange Commission (SEC), the U.S. Commodity Futures Trading Commission (CFTC), and the Board of Governors of the Federal Reserve System. OCC has more than 100 clearing members and provides central counterparty (CCP) clearing and settlement services to 19 exchanges and trading platforms. More information about OCC is available at www.theocc.com. Benefits A highly collaborative and supportive environment developed to encourage work-life balance and employee wellness. Some of these components include: • A hybrid work environment, up to 2 days per week of remote work • Tuition Reimbursement to support your continued education • Student Loan Repayment Assistance • Technology Stipend allowing you to use the device of your choice to connect to our network while working remotely • Generous PTO and Parental leave • 401k Employer Match • Competitive health benefits including medical, dental and vision Visit https://www.theocc.com/careers/thriving-together for more information. Compensation • The salary range listed for any given position is exclusive of fringe benefits and potential bonuses. If hired at OCC, your final base salary compensation will be determined by factors such as skills, experience and/or education. • In addition, we believe in the importance of pay equity and consider internal equity of our current team members as part of any final offer. • We typically do not hire at the maximum of the range in order to allow for future and continued salary growth. We also offer a substantial benefits package as noted on www.theocc.com/careers • All employees may be eligible for a discretionary bonus. Discretionary bonuses are based on various factors, including, but not limited to, company and individual performance and are not guaranteed. Salary Range $167,800.00 - $226,400.00 Incentive Range 18% to 25% This position is eligible for an annual discretionary incentive compensation award, for which the target range is listed above (see Incentive Range ). The amount of such award, if any, will be based on various factors, including without limitation, both individual and company performance. Step 1 When you find a position you're interested in, click the 'Apply' button. Please complete the application and attach your resume. Step 2 You will receive an email notification to confirm that we've received your application. Step 3 If you are called in for an interview, a representative from OCC will contact you to set up a date, time, and location. For more information about OCC , please click here . OCC is an Equal Opportunity Employer

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