Principal, AI-Native SDLC Architecture

The Options Clearing Corporation
Chicago, IL
What You'll Do:

Ready to make your application Please do read through the description at least once before clicking on Apply.

OCC is transforming how its technology organization builds software. We have deployed AI-assisted development tools across the firm, enabled citizen development, and established AI governance. The next step is redesigning our software development lifecycle to be AI-native from the ground up - with graduated, tiered standards that work for everything from personal productivity tools to SCI-grade production systems.

Research from Stanford, HumanLayer, and Qodo consistently finds that the documentation and codified practices sufficient for experienced human developers are not detailed enough to drive consistent results from AI agents. Raising that bar benefits everyone - human developers onboard faster, key-person risk drops, and cross-team consistency improves. This role designs graduated standards and practices detailed enough that any competent developer, human or AI, can consume them and produce working code.

You will design a graduated SDLC framework with prescriptive practice standards at each tier of criticality, pilot with real development teams, and drive adoption across the enterprise. The deliverable is a working development lifecycle - not a document.

This is a rare opportunity to define how a critical financial market utility builds software in the AI era. You will have executive sponsorship, organizational mandate, and the backing to make standards enforceable rather than advisory.

Primary Duties and Responsibilities:

To perform this job successfully, an individual must be able to perform each primary duty satisfactorily.

Design Graduated SDLC Standards and Practices
  • Define prescriptive practice standards across multiple tiers of development criticality - from personal experimentation through operationally critical, SCI-adjacent systems
  • Establish standards across key dimensions: structure, testing, documentation, error handling, dependencies, storage, review, and operability
  • Elevate existing documentation, architecture decisions, integration patterns, and deployment procedures to the level of detail that drives consistent results from both human and AI developers
  • Design documentation and testing standards that serve double duty: readable by human developers joining a project and consumable by AI agents starting a coding session
  • Encode tier-appropriate standards into persistent context files ( , , planning templates) as a natural output of well-documented practices - not as a separate AI-specific exercise
  • Design graduation triggers and assessment mechanisms for artifacts moving between tiers
Enable Citizen Development at Scale
  • Create low-friction pathways for lower-tier development that enable experimentation without bureaucratic overhead
  • Design intake, classification, and registry processes for citizen-developed tools - visibility without paralysis
  • Solve the path from working prototype to supported environment at every tier
Drive Organizational Adoption
  • Pilot the graduated SDLC with 2+ development teams, iterating based on real-world feedback
  • Build alignment across Engineering, Architecture, Security, QA, and Governance/Risk functions
  • Establish a quarterly organizational learning system where operational data, code review patterns, graduation assessments, and incident post-mortems feed back into living standards
  • Develop training and coaching programs that help developers at every level internalize the standards - not just comply with them
Connect to Enterprise Architecture and Governance
  • Provide the practice standards layer underneath the existing governance framework
  • Ensure standards satisfy regulatory requirements (Regulation SCI, CPMI-IOSCO, internal audit)
  • Coordinate with enterprise architecture to ensure SDLC standards reflect infrastructure reality
How This Role Works

This is a senior individual contributor role that leads through influence and organizational authority, not direct management. You will build consensus across multiple functions while being opinionated enough to define standards with teeth. You will have executive sponsorship from the CSO and CIO to make standards enforceable.

If you have spent your career building things that other people's processes depend on, and you are frustrated by organizations that treat development standards as optional guidelines, this role exists to fix that.

What Success Looks Like
Timeline
Milestone
90 Days
  • Current SDLC variations assessed. Tier structure validated with stakeholders. Ownership model resolved.
6 Months
  • Practice standards published for all tiers. Context engineering templates in use. Pilot underway with 2+ teams. Intake and classification process operational.
12 Months
  • Standards organizationally agreed and ready for enterprise rollout. Automated validation gates active. Learning system operational with first quarterly review completed.
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.

  • 10+ years in software engineering, architecture, or development methodology roles
  • Demonstrated experience designing and implementing SDLC standards or development practice frameworks at organizational scale - not single-team
  • Hands‑on experience with AI coding agents (Claude Code, GitHub Copilot, Cursor, or equivalent) in real codebases - not just demos
  • Working knowledge of context engineering: persistent context files, research-plan-implement workflows, progressive disclosure, context window management
  • Experience with brownfield/legacy codebases - understanding why AI-assisted development in complex existing systems is fundamentally different from greenfield
  • Strong facilitation and coalition-building skills - ability to drive alignment across engineering, security, architecture, and governance functions
  • Excellent written and verbal communication - ability to translate technical concepts for executives and organizational standards for AI agents
Preferred Qualifications
  • Experience in financial services, particularly regulated environments (SIFMU, bank, exchange, clearinghouse)
  • Familiarity with NIST AI Risk Management Framework, Regulation SCI, or CPMI-IOSCO principles
  • Experience with CI/CD pipelines, automated testing frameworks, and quality gate enforcement
  • Background in organizational change management - understanding that SDLC transformation is a culture change, not a standards document
  • Track record of staying current with rapidly evolving AI development practices - demonstrated through conference participation, publication, or community engagement
What We Offer
  • The chance to define how a SIFMU builds software in the AI era - a problem very few organizations are solving at this level of rigor
  • Executive sponsorship and organizational mandate to make standards enforceable
  • A leadership team that understands context engineering, has studied the research, and is committed to AI-native transformation - not just AI adoption
  • Competitive compensation commensurate with the Principal level
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
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 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

$175,100.00 - $282,800.00

Incentive Range

This position is eligible for an annual discretionary incentive compensation award, for which the target range is listed above (see Incentive Range). xrczosw The amount of such award, if any, will be based on various factors, including without limitation, both individual and company performance.

OCC is an Equal Opportunity Employer

Posted 2026-06-18

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