Founding Head of Engineering (Path to CTO) - VC Backed Generative AI FinTech

Stealth Startup; Illinois; On-site; USD 225,000 - 275,000; Full time

Job summary

A pioneering fintech company is looking for a Founding Head of Engineering to develop and scale an innovative AI Financial Engine. You will collaborate closely with the CEO to make critical decisions, build a product that addresses consumer debt, and lead a team in a startup environment. Ideal candidates are full stack engineers with experience in application layer AI and a passion for driving impactful fintech solutions. The role offers a competitive salary and a significant place in building a transformative financial platform.

Qualifications

• Strong experience in creating scalable platforms and products.
• Ability to work cross-functionally with various teams.
• History of taking products from zero to one.

Responsibilities

• Own the hardening, scaling, and expansion of the AI Financial Engine.
• Work closely with the CEO on architectural decisions.
• Build and scale both product and engineering teams.

Skills

Full stack engineering

Application layer AI

Experience in Consumer FinTech

Startup environment experience

Leadership skills

Customer-driven product development

Education

Degree in computer science or related field

Job description

Founding Head of Engineering (Path to CTO) - VC Backed Generative AI FinTech

We’re on a mission to help consumers reduce their consumer debt burdens with smarter tools and financial insight. We are building infrastructure to eliminate the “Inertia Tax” that keeps Americans trapped in high interest debt. Our first focus area is credit cards, taking on incumbents with multi‑billion dollar valuations that make money through affiliate fees for marketing consumer credit cards. We have a new model to earn trust with consumers and add 10X the value for these consumers as they evaluate the best credit cards for them. We then develop and implement a plan to reduce their debt exposure via a proprietary LLM. We have deep connections to some of the largest consumer affiliate networks in the country who see how our product is a game‑changer for the consumer, and who we partner with as a distribution hack to acquire customers at scale. We also have partnerships with key financial institutions to drive distribution. This is an opportunity to build a company that already has funding, has a clear path to venture scale, already has a product in market, a monetization path built on existing payment rails, and with an incredible wedge first product that can be expanded to a much broader consumer finance platform in a massive market. We now want to partner with an elite technical leader to take us from prototype to a scalable, bank‑grade platform.

The Role

You’ll own the hardening, scaling, and expansion of our Vertical AI Financial Engine. We have today a prototype in market that is delivering material customer value across a cohort of design partners. You’ll incorporate product learnings from this prototype to develop a scalable platform working in close collaboration with the CEO who is a known FinTech operator that has scaled multiple unicorns and most recently was Chief Product Officer for a $2B Series E InsureTech. This role starts as a senior principal engineer role, but will quickly move into a founding head of engineering (with potentially a path to CTO) where you will build and scale both a product and engineering team, depending on your interest. You are a full‑stack engineer that relishes hard problems with a specialty in back‑end and a deep interest in application layer AI. You’ve brought multiple products from zero to one and want to do this again with an exceptional team to support.

Why This Role?

• Partner, Not Employee: You will work directly with the CEO to make every critical architectural decision. You will hire the engineering team, choose the stack, and define the engineering culture.
• Massive Scale & Impact: We are tackling a $1.1 Trillion problem. The code you write will directly save families thousands of dollars annually.
• Deep FinTech DNA: You are joining a veteran team that knows exactly how to scale venture‑backed fintech.

Signals You’re the Right Fit

• Full stack engineer with evidence of working in application layer AI
• Experience building in FinTech and, plus, if that is in Consumer FinTech
• Lots of experience and a love of working in a startup environment
• Degree in computer science or a related field
• Proven ability to take products from zero to one in fast‑paced, ambiguous environments
• Experience working cross‑functionally with product, design and marketing teams
• Proven leader with the ability to build and scale high‑performing teams
• Proven ability to build incredible trust with team members, investors and customers
• Deep focus on customer‑driven product development
• Lots of evidence of rolling up your sleeves and getting in the trenches to solve problems
• Deeply curious and passionate about creating new things
• Strong bias for action and deep ownership in your work
• Driven by a desire to build a scalable business and thrive as both leader and builder
• Low ego with a high EQ

Next Steps

If this role sounds like it would be a fit for you, please apply through this link.

Location: Chicago, IL. Salary: $225,000.00 – $275,000.00. Role: Mid‑senior level, Full‑time.