Head of Engineering

Rockstar is recruiting for a VC-backed fintech startup that is building the future of self-driving money. The company has created an intelligent money management engine that connects to user accounts, studies income and spending, and automatically executes smart financial actions on their behalf. This small, ambitious team is building an AI-driven platform with real users and meaningful enterprise partnerships, moving quickly with a deep commitment to quality and collaboration.

We’re looking for a senior technical leader to own engineering and product execution end-to-end. As the partnership proves out, we would love for this individual to evolve into CTO and technical co-founder. This role sits at the intersection of hands-on building and strategy—partnering closely with the CEO while leading the engineering and product team. Bonus points if you’ve done this before at a VC-backed startup.

About the company

Fintech has spent the last decade teaching people to look—at their spending habits, their goals, their balances. But looking isn’t doing.

This company closes that gap—it connects to your accounts, studies your income and spending, and automatically executes smart money moves on your behalf. It’s the future of self-driving money.

- If you’ve got too much cash sitting idle in checking, it moves it to a higher-yield account.

- If a bill is coming due, it makes sure you’re liquid before paying it.

- If your student loan interest spikes, it makes sure you pay extra this cycle.

- If it’s January 1st, it’ll make sure you contribute to your IRA.

It’s intelligent orchestration—a money management engine running quietly in the background.

At the core is a network of AI agents that act as a financial “brain.” They are building intelligent systems that reason over financial data, evaluate tradeoffs in real time, and take action on a user’s behalf.

They are a small, VC-backed team building an ambitious product with real users and enterprise-level partnerships. They move quickly, care deeply about quality, and most importantly, respect each other and the commitment they’ve made to building something meaningful together.

If you’re excited about building early, joining a tight-knit team, owning meaningful problems, and helping define a new category in personal finance, you’ll feel at home here.

Responsibilities

- Own engineering end-to-end: architecture, technical direction, quality, and scalability

- Lead delivery across product and engineering—turning product goals into shipped reality

- Design, build, and own AI-driven systems, including agents, decision engines, and model-backed workflows

- Set the technical strategy for how they use AI responsibly, reliably, and at scale

- Stay hands-on in the code while also setting the long-term technical vision

- Lead and mentor the engineering team; help build the team and culture over time

- Partner closely with the CEO on roadmap decisions, sequencing, and technical tradeoffs

- Make clear, pragmatic decisions around build vs buy, infrastructure, and integrations

- Anticipate technical risk and address it before it becomes a blocker

Requirements

- Senior engineering experience with real ownership of systems in production

- Strong technical judgment and comfort making tradeoffs in an early-stage environment

- Experience working closely with founders and product leaders

- Ability to move fluidly between coding and strategy without losing speed

- Clear communicator who can explain technical decisions simply and directly

- High-ownership mindset—cares deeply about what is built and shipped

- Excited by the idea of growing into broader technical leadership as the company scales

- Strong experience building with AI models and systems, not just calling APIs

- Experience designing agent-based systems or multi-step AI workflows

- Familiarity with orchestration patterns for agents (state, memory, tools, retries)

- Robust familiarity with the current tech stack: Python, Django, Flask, React Native, Expo, OpenAI, AWS

You’ll be a good fit if, as an engineer, you:

- Treat the codebase like it’s yours (even if you didn’t write it)

- See something broken and fix it without being asked

- Are meticulous to a fault when it comes to QA and attention to detail

- Fundamentally understand that speed and quality are not tradeoffs

What you get

- A fast-paced and collaborative start-up environment

- Competitive compensation

- Equity options at a well-funded, VC-backed startup

- Medical, dental, and vision coverage

Keep in mind

- This role is remote; candidates based in or near NYC are a plus

- The team meets in person a few times a year for 3–5 day team offsites

- They primarily work Eastern Time

- As an early-stage startup, the schedule oftentimes extends beyond typical 9–5 hours. If you are looking for a strict 9–5 (without any evening or weekend work), this role is not for you.