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.

FairSquare 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.

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 explainability and audit standards for AI output.
• Own system infrastructure end to end: functionality, resilience, security, and the platforms our AI work depends on.
• Define and report the measures that matter — adoption, accuracy, override and correction rates, cycle-time impact and return on investment — and carry that story, good news and bad, to the President and the Board.
• Partner across every function to put technology and AI to profitable use: treat internal colleagues as customers, go to the person rather than around them, name the friction you find in a process instead of quietly working around it, and use what you hear back to adjust course.
• Coach, develop and retain a distributed team of software, data science, AI and IT professionals — keeping real development plans in place for your leaders and yourself, and working with HR on the AI fluency, reskilling and change management that enterprise AI adoption genuinely requires.
• Lead in line with our policies and applicable law: hiring and training, planning and directing work, and developing and rewarding performance.

What You Bring

• A bachelor’s degree in computer science, engineering, data science or a related field; a master’s or PhD in AI/ML is preferred.
• At least 10 years in technology roles, including hands-on exposure to AI/ML or data science, and at least 5 years leading people.
• A track record of owning budgets and business planning at scale — and of delivering what you committed to, on the date you committed to it.
• Strategic range — the ability to set a direction across both the technology and the AI domains, then execute it: consulting widely before you decide, and moving with real urgency once you have.
• Deep technical knowledge of cloud platforms, mobile applications and generative AI, and a clear sense of how they apply to financial services and lending.
• Real experience with AI governance, model risk management and regulatory compliance — including fair-lending regulation (for example ECOA / Regulation B) and data privacy.
• Communication skill that travels: you can explain an AI capability, and its risk, to an engineer and to a director in the same week — and you disagree openly before a decision is made rather than relitigating it afterward.
• Leadership and organizational ability across a distributed, cross-functional operating model, with a record of growing people and not only shipping projects — the leaders you have developed are the evidence.
• Sound judgment about when AI is the right answer — the confidence to say when it is not, and the self-awareness to name your own blind spots before someone else does.

Why This Role Is Different

Most technology executives inherit a roadmap. You will inherit a mandate.

FairSquare has made a deliberate decision to treat AI as an operating-model question rather than a procurement one — which means the person in this seat gets to redesign how work actually moves through the company, not just buy the software that supports it. Executive leadership and the Board are already engaged and expect to be held to evidence. The budget is real. The scope is the enterprise.

It is also a role with a conscience attached. Every role here touches a customer, and the standard we hold ourselves to is that we can always explain how a decision was made and who was accountable for it. Small businesses risk it all for a dream; we risk it all to make sure they win. If that constraint reads to you as the interesting part of the problem rather than the annoying part, you are the person we are looking for.

Compensation & Location

Salary range: Base Salary: $290K-375K. Position eligible for additional incentives including bonus, equity, 401(k) match, health and welfare benefits, amazing culture, growth opportunity and more.

Location: This position is a Hybrid role and will work from our offices in either: San Diego, CA; Atlanta, GA, or Orlando, FL.

FairSquare is an equal opportunity employer.