Chief Information & AI Officer

FairSquare•San Diego, CA

1d•$290,000 - $375,000•Hybrid

About The Position

FairSquare is seeking a Chief Information & AI Officer to lead its technology organization and build a robust AI integration strategy. This executive will own the full technology stack, including software engineering, data, infrastructure, security, and IT. A key responsibility will be defining how AI is used in a small-business lending company, determining which tasks AI can perform autonomously, which require human oversight, and which should remain entirely human-led. The role requires developing an operating model and guardrails for AI implementation, defending the strategy to the Board, regulators, and funding partners, and providing evidence of its effectiveness. The ideal candidate believes that sustainable AI advantage comes from accountability rather than early adoption.

Requirements

Bachelor's degree in computer science, engineering, data science, or a related field.
At least 10 years in technology roles, with hands-on exposure to AI/ML or data science.
At least 5 years of experience leading people.
Track record of owning budgets and business planning at scale.
Proven ability to deliver on commitments by agreed-upon dates.
Strategic range to set direction across technology and AI domains and execute it.
Deep technical knowledge of cloud platforms, mobile applications, and generative AI, with application to financial services and lending.
Experience with AI governance, model risk management, and regulatory compliance (e.g., fair-lending, data privacy).
Strong communication skills, able to explain AI capabilities and risks to diverse audiences.
Leadership and organizational ability across a distributed, cross-functional operating model.
Record of growing people and shipping projects.
Sound judgment regarding the appropriate application of AI.

Nice To Haves

Master's or PhD in AI/ML is preferred.

Responsibilities

Set the technology and AI strategy for the enterprise, tied to Key Goals and business outcomes.
Identify and deploy technologies, including AI and machine learning, that create competitive advantage in fintech.
Establish and lead an AI Center of Excellence to set standards, share tooling, and disseminate best practices.
Prioritize and sequence AI use cases enterprise-wide using a risk-tiered framework, distinguishing between full automation, human oversight, and human judgment.
Build governance for AI, including model risk management, data protection, quality assurance, fair-lending compliance, and explainability standards.
Own system infrastructure end-to-end, including functionality, resilience, security, and AI platform support.
Define and report key performance metrics such as adoption, accuracy, override rates, cycle-time impact, and ROI.
Partner across functions to leverage technology and AI for profitable use, treating internal colleagues as customers.
Coach, develop, and retain a distributed team of software, data science, AI, and IT professionals.
Lead in accordance with company policies and applicable law, including hiring, training, planning, directing work, and performance management.