Head of Engineering

👶 About Junior

Junior is building the AI operating system for investment research.

Our software helps private equity firms, consultants and financial institutions complete high-stakes research workflows dramatically faster — from diligence and memo writing to market mapping, research synthesis and strategic analysis.

We’re building toward a future where AI can run substantially more of that work: conducting research, understanding evidence and producing outputs customers can use to make decisions.

• Bootstrapped and profitable

• ~$28M+ ARR, after growing 10x last year

• 65+ people across New York, London and Sydney

• ~20-person engineering team across four to five teams

• Trusted by leading private equity firms, consultancies and financial institutions

• Core stack: TypeScript, Next.js and PostgreSQL

AI-assisted development has already changed how quickly we can build. Our current engineering team operates with the output of a much larger organization — and that pace is only increasing.

We’re now looking for someone to build the engineering organization for Junior’s next chapter.

💡 The role

• You’ll report to our CTO and own the day-to-day operation of engineering: people, planning, delivery, reliability and recruiting.

• The CTO will continue to own product and technology direction, frontier experimentation, AI-native development and consequential long-term architecture.

• You’ll turn that direction into results.

• You’ll have the authority to challenge scope, sequencing and commitments when they aren’t credible — and the responsibility to make sure the organization delivers on the ones it makes.

This is not a role where you spend your first three months observing from the sidelines.

You’ll begin by doing the work:

• Ship production code

• Learn our systems and development tools

• Join architecture and debugging discussions

• Work directly with engineers, Product and customers

• Take an on-call shift

• Build firsthand context before changing how the organization operates

You’ll progressively take ownership of engineering operations, but this will remain a deeply technical leadership role. You’ll stay close to the code, architecture and important production problems.

🎯 What you’ll own

• Delivery: Set clear priorities, owners and achievable scope across Engineering, Product and Design

• Engineering leadership: Develop hands-on Engineering Leads who can run strong, autonomous teams

• Organization design: Build a lean organization capable of growing toward 40–60 engineers where the business justifies it

• Recruiting: Own engineering hiring and help us maintain a very high technical bar as the team grows

• People: Lead feedback, performance and development while giving excellent ICs room to grow without becoming managers

• Reliability: Establish clear ownership of critical systems, improve incident response and eliminate recurring failures

• Engineering effectiveness: Remove friction across tooling, testing, reviews and delivery

• AI-native development: Turn AI-assisted engineering into measurable improvements in speed and quality

• Financial ownership: Own engineering’s infrastructure, tooling and AI spend — and be accountable for the value we get from it

The goal is not to add process for the sake of it. It’s to introduce structure where it helps us move faster — and remove it when it doesn’t.

🚀 What success looks like

In your first 90 days

• You’ve shipped meaningful production code

• You understand the systems, team and customers

• You’ve earned technical trust across the organization

• You’ve established clear operating baselines

• You’ve identified a small number of high-impact improvements grounded in firsthand experience

By six months

• You own routine engineering operations and most engineering recruiting

• Every team has clear ownership and strong leadership

• Commitments are more credible and risks surface earlier

• The CTO spends substantially less time assigning work and chasing project updates

• Engineering ships faster with fewer recurring failures

• Engineers still have autonomy, direct founder access and room to pursue ambitious ideas

• The impact of engineering work is clearly connected to customer and business outcomes

🔥 About you

• You’re still deeply technical and can write production code, understand unfamiliar systems and debug difficult problems

• You’ve led engineering teams through meaningful growth and ambiguity

• You can point to specific improvements you’ve made across delivery, reliability and organizational clarity

• You’ve hired excellent engineers and developed strong ICs and engineering leaders

• You’re comfortable giving difficult feedback and making performance decisions

• You know when management and process help — and when they get in the way

• You’ve built software where reliability, security and customer trust genuinely matter

• You use AI development tools thoughtfully and have strong views on how they will change engineering teams

• You can challenge a highly technical founder constructively

• You want to work closely with Product, customers and the codebase

• You’re based in New York, or committed to relocating, and excited to work with the team in person

We care far more about what you’ve personally built, owned and improved than your previous title.

Prior VP or Head of Engineering experience is not required.