Chief Information & AI Officer

About FairSquare

FairSquare is a technology-driven financial services company serving small businesses across the United States. We began with a singular focus to bring accessible working capital to our nation’s small businesses and have evolved into a full suite of financial products and the ability to cater to every business need. We combine capital, data and technology to get funding into the hands of business owners quickly and responsibly. Founded in 1999, our subsidiary brands offer a range of diverse financing options from premier small business loans to self-service digital lending platforms that support the needs of our customers throughout every stage of their business journey.

The Role

Reporting directly to the President and serving on the executive leadership team, the Chief Information & AI Officer sets and drives FairSquare’s combined technology and artificial intelligence strategy — ensuring our software, infrastructure and AI systems run efficiently, profitably, securely and responsibly. This is a builder’s seat, not a caretaker’s. You will make executive technology and AI decisions on behalf of the company: owning the technology and AI budget, aligning investment with our vision and our stakeholders’ needs, sequencing AI use cases against a risk-tiered framework, and uniting software engineering, data science, AI and IT into one team that can actually execute against the strategy you set. You will also lead it the way we expect every leader at FairSquare to lead — commitments owned and delivered on time, problems surfaced before they become surprises, disagreement voiced at the table rather than after the meeting, and full commitment carried forward once a decision is made.

What You Will Do

• Set the technology and AI strategy for the enterprise, and keep it tied to our Key Goals and business outcomes rather than to tooling.
• Find and deploy the technologies — including AI and machine learning — that create genuine competitive advantage in fintech, and say no to the ones that do not.
• Curiosity about what is new, discipline about what is worth it.
• Stand up and lead an AI Center of Excellence: the central hub that sets standards, shared tooling and playbooks for AI leads embedded across the business — and that spreads what works instead of letting it stay in one team.
• Prioritize and sequence AI use cases enterprise-wide against a risk-tiered framework, distinguishing what can be automated outright from what requires human oversight or human judgment alone — and deciding in the customer’s favor when the trade-off is close.
• Build the governance that makes speed defensible — model risk management, data protection, quality assurance, fair-lending and regulatory compliance, and explain