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. What You'll Do

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.

Responsibilites

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.

Requirements

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 tradeoffs between speed, quality, and scope.

Data-driven and product-oriented mindset, comfortable using metrics to guide strategy and decision-making.

Strong communication and executive presence; comfortable working closely with founders, C-suite, and external stakeholders.

Low ego, high ownership mentality with a bias toward action and “win together” mentality.

Location

Based in (or willing to relocate to) the New York City area, with regular in-office collaboration with the engineering and product teams.

Benefits & Why Join

Own the Engineering Function

Step into a true VP seat with broad scope and autonomy, reporting at the executive level and shaping both technology and product direction.

Build the Next Generation of Career Tools

Work on an ambitious roadmap made possible by Generative AI: dynamic resume/cover letter generation, rich job and company intelligence, and agentic career coaching that can support millions of professionals.

Massive, Timely Market Opportunity

Help professionals navigate peak job insecurity at a time when demand for smart, AI-powered career tools is surging. Your work will have direct, tangible impact on people’s financial and professional lives.

World-Class Talent & Culture

Lead a high-caliber engineering team in NYC, set the bar for excellence, and build a culture that is fast, thoughtful, and deeply collaborative.

Growth & Upside

Join a scaling company in a critical stage of evolution, with the opportunity for significant professional growth, influence, and impact.