Head of Engineering

The Opportunity

We need someone with 5+ years of engineering experience (the range we're aiming for is about 5–10 years) in backend systems, data, infrastructure, or applied AI, who has led engineers or driven a large project with several contributors to success. You should be comfortable working with a lot of ambiguity as a hands-on tech lead/manager (TLM): about 70–80% coding and 20–30% leadership. You should have a track record of shipping production software and making a team more effective. Bonus points if you're a former founder or founding engineer, have startup experience (Series A–C or another high-bar tech company), or have done forward-deployed work with enterprise customers.

What You'll Be Doing

• Act as the engineering lead the CTO can rely on while he spends more time on sales and customers. You'll design and build the backend, data, and AI systems behind enterprise deployments.
• Own technical direction and make clear calls on architecture, vendors, and build vs. buy. Guide junior engineers toward better system design.
• Work closely with the founders, engineers, and customers (REITs, real estate PE funds, and asset managers such as a $90B global real estate firm) to make sure every client engagement stays on track.
• Set practical standards for code quality, security, testing, observability, and running what we ship.
• Lead enterprise deployments from kickoff to delivery. This includes going on-site with clients to deal with messy data, ERPs, and legacy systems, and turning customer-specific work into reusable infrastructure (knowledge graphs, ontologies, company-brain systems).
• Coach engineers and give specific feedback. Hold the team accountable on timelines, have the hard conversations, spot risks early, and help hire and grow the team as the company scales.

Why This Role

• Massive, Untouched Market: Trillions in physical-development spend with almost no real software. The company builds AI employees for the largest REITs, institutional developers and asset managers in North America — including a $90B global real estate firm.
• Revenue Inflecting: Annualized revenue quadrupled in March. A 6-person seed-stage team ($2.5M raised) landing enterprise accounts faster than it can staff them.
• Founding Team Pedigree: A repeat founder who exited to a Fortune 500, a former tech lead at Meta Superintelligence, and a development director who delivered $2B+ of projects.
• Be the Engineering Leader: Hands-on TLM (70–80% code) who becomes the CTO's right hand as he shifts to customers — own architecture, build-vs-buy, standards, hiring and enterprise deployments end to end.

Key Requirements

• Has led and managed an engineering team, setting priorities, coaching engineers and holding them accountable (as an EM, TLM, Tech Lead or founding CTO); a Head of Engineering title isn't explicitly required
• Still writes production code in their current or most recent role
• 5+ years of software engineering experience, including time leading and managing an engineering team (as an EM, TLM, eng lead or founding CTO)
• Experience at VC-backed startups (Series A-C) or top-tier technology companies (e.g. Waymo, Databricks)
• Technical depth in production systems engineering, e.g. Python or TypeScript, SQL, AWS, enterprise data platforms (Snowflake, Databricks) and AI model APIs

Nice to Have

• Experience as a startup founder or founding engineer
• Background building enterprise app generation or fleet management products

Interview Process

1. Initial Screening with Alexander Wu (CEO) (30 minutes) — A general first call covering the candidate's background and leadership experience, company signal (startup or high-bar company experience), years of experience, and culture fit: high energy, high agency, comfort with ambiguity, and excitement about the mission. The call is recorded. Sai Y (CTO) reviews the recording and decides whether the candidate moves to the Technical Deep Dive or goes straight to the Work Trial.
2. Technical Deep Dive with Sai Y (CTO) (1 hour) — May be skipped if the screening already gave enough signal. The candidate shares their screen and works through a systems question in a shared Google Doc, using any programming tool they like. Tests system design judgment and hands-on technical ability, plus a Meta-style behavioral and scenario part (e.g. 'pretend I'm a customer and an engagement is starting, what do you do?') to show how they'd run a rollout, lead engineers and handle ambiguity.
3. Work Trial (Varies) — The candidate works in person alongside the company team on real work. The founders fully assess technical depth, leadership and accountability, how the candidate works with the team, and culture fit. If the trial goes well, the next step is an offer.

About the Company

• Space: AI, Real estate, Construction
• At a glance: Team of about 6, founded 2025, $2.5M raised

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Application Questions

1. Why do you think they'd be a great fit?
2. How many engineers have you managed or led, and in what role?
3. Why are you interested in joining an early-stage startup?
4. Can the candidate be on-site? If not, is the candidate willing to relocate?