VP, Engineering

About Ladders

Celebrating 20 years, Ladders delivers more $100K+ job interviews to our 8M members. As a leader in applying AI to the job search, we’re always innovating better ways to make your job search shorter and more productive.

We're a profitable, small, collaborative, venture‑backed business based in New York City.

VP, Engineering

The VP, Engineering will own the end‑to‑end engineering function for a New York–based product and platform team. This leader will be responsible for building and scaling the technology organization that powers a high‑traffic consumer marketplace, an employer/recruiter platform, and a rapidly expanding suite of Generative AI–driven career tools.

This is a New York, NY‑based hybrid role.

• Lead a NYC‑based engineering team (and distributed collaborators) responsible for the core job marketplace, user experience, personalization, and internal platforms.
• Architect and deliver an ambitious product roadmap that includes; dynamic resume and cover letter generation, deep, structured company and job data to power search and matching and agentic, AI‑powered “career coaching” experiences for job seekers
• Build and scale world‑class engineering teams, processes, and systems that allow the company to ship quickly, safely, and with high quality.
• Partner closely with Product Design, Data, and Operations to define technical strategy and translate business goals into scalable, resilient systems.

This is a highly visible leadership role for someone who wants to hire the best talent in the market, move fast, and win.

• Technical Leadership & Strategy
• Define and own the engineering vision, strategy, and operating model in partnership with the executive team.
• Drive the technical roadmap for a modern, cloud‑native, high‑scale web and mobile platform.
• Champion the design and implementation of Generative AI and ML systems into user‑facing experiences and internal tools.
• Team Building & People Leadership
• Build, lead, and mentor a high‑performing NYC‑based engineering organization, including engineering managers and senior ICs.
• Attract and retain top engineering talent; establish a strong recruiting brand and a rigorous hiring bar.
• Foster a culture of ownership, psychological safety, and high performance with clear standards and accountability.
• Execution & Delivery
• Ensure the engineering organization consistently delivers against the product roadmap with predictable velocity and quality.
• Implement best‑in‑class practices for architecture, testing, observability, incident management, and reliability.
• Balance short‑term product delivery with long‑term platform investments (data, infrastructure, and shared services).
• Stakeholder Management & Cross‑Functional Collaboration
• Work closely with Product, Design, Marketing, Sales, and Customer Success to align on priorities and tradeoffs.
• Translate complex technical concepts into clear language for non‑technical stakeholders and the board.
• Represent engineering in company‑wide planning, forecasting, and strategic initiatives.

• Experience
• 10+ years of progressive engineering experience, including 5+ years leading engineering teams at the Director/VP level or equivalent.
• Proven track record scaling engineering organizations supporting consumer web/mobile products or marketplaces; experience with two‑sided platforms is a plus.
• Hands‑on experience building or integrating AI/ML products, ideally including Generative AI (LLMs, retrieval‑augmented generation, recommendation systems, or similar).
• Strong background working in high‑growth environments where speed, experimentation, and iteration are critical.
• Technical & Leadership Skills
• Deep understanding of modern web architectures, distributed systems, and cloud infrastructure.
• Strong opinions on engineering best practices: testing strategy, CI/CD, observability, performance, and security.
• Demonstrated success hiring, developing, and retaining top engineering talent in competitive markets like NYC or similar hubs.
• Ability to build and manage a multi‑level org (ICs, tech leads, EMs) and evolve structure as the company scales.
• Leadership Qualities
• Ruthless prioritization skills; capable of making…