About the role

As the first engineer at Squad, you'll own one of the hardest challenges in tech: predicting which humans will thrive where.

We've already solved the cold start problem. We have hundreds of users generating thousands of data points every day. The foundation is there. Now comes the fun part: endless room to build, and you'll shape what that looks like.

You'll take full ownership of anything AI at Squad - technical vision, execution, and the decisions that shape what this company becomes. This isn't a role where you inherit a roadmap. You'll collaborate directly with the founder to figure out what to build, how to build it, and who else we need on the team.

Predicting human fit is one of the hardest recommendation problems out there - sparse feedback, subjective preferences, high stakes. Most hiring AI trains on the same public data everyone else has. We have proprietary signal from both sides of the market that no one else sees. No one has built on a foundation like this before.

You'll work on things like:

• Building recommendation systems that predict candidate-job fit - and get smarter with every hire, rejection, and feedback loop
• Designing AI agents that automate end-to-end recruiter and ops workflows
• Fine-tuning models on proprietary hiring data no one else has access to
• Evaluation and simulation environments to measure and improve match quality
• And much more which you'll define, across matching, automation, and infrastructure.

We'll be most excited if you have:

• High ownership, comfort with ambiguity, bias toward shipping
• 3+ years of software engineering experience, with a track record of shipping full-stack AI/LLM features in production
• Proficiency with modern AI/ML technologies (LLM APIs, embeddings, vector databases, fine-tuning)
• Experience in a high-intensity, high-velocity environment (e.g., seed or Series A/B startup, high-growth tech company, 01 product team)

We're hiring across levels - whether you have 3 years of experience or 10, what matters is the intensity and ownership you've demonstrated.

Working with us

Squad is based in New York, with our team working out of a beautiful office in Flatiron.

We run a high-trust environment with real autonomy and ownership. We provide competitive compensation with meaningful equity to reflect that. Everyone who joins early will be a major contributor to our success.

We also provide benefits to ensure you can focus on creating impact:

• Health insurance
• Unlimited PTO
• Lunch at the office every day and dinner after 7pm (usually fresh healthy food from Eataly)

Our salary ranges are based on paying competitively for our company's size and industry, and are one part of the total compensation package that also includes equity, benefits, and other opportunities at Squad (for full-time employees). Individual pay decisions are ultimately based on a number of factors, including qualifications for the role, experience level, skillset, geography, and balancing internal equity.