Chief Information & AI Officer

• Full-time, Executive
• Reports to the President

• Full-time, Executive
• Reports to the President

Location:

hybrid Atlanta, San Diego & Orlando

Every lender in the country can buy the same AI models on the same afternoon. Almost none of them have worked out how to put those models to work in a business where a wrong answer is a regulatory event — and, for the owner on the other end, a payroll that does not get made. That is the job.

Fair Square is looking for a Chief Information & AI Officer to lead our technology organization — and to build something most companies our size are still only talking about.

You will own the full technology stack: software engineering, data, infrastructure, security and IT. On top of that, you will own a harder question. In a small-business lending company, which work should AI simply do? Which should AI draft, with a named human accountable for the result? And which should never leave human hands at all? Your answer has to hold up three ways at once — for a regulator, for a funding partner, and for the business owner waiting on a decision.

Nobody is going to hand you that answer. You will be the executive who collaborates with the team to define it, builds the operating model and the guardrails that make it real, defends it to the Board and to our regulators and funding partners, and then proves — with evidence, not anecdotes — that it works. You will raise the obstacles early, while they are still cheap to fix, and own the outcome either way.

If you believe the durable advantage in AI belongs to the companies that make it accountable rather than the ones that adopt it first, we should talk.

Fair Square 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.

Reporting directly to the President and serving on the executive leadership team, the Chief Information & AI Officer sets and drives Fair Square’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 Fair Square 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.

• 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…