Full time Product & Engineering At Stay22, we’re revolutionizing how people convert online. Our AI‑powered affiliate platform helps publishers, ticketing platforms, and content creators unlock new revenue streams while levelling up their audience's user experience. Stay22 is seeking a Head of Engineering to lead and scale our engineering organization as we enter our next phase of growth.

This is a senior leadership role responsible for shaping our technical vision, engineering strategy, and execution across multiple squads, while maintaining strong technical credibility with the team. Reporting directly to the CTO, the Head of Engineering will oversee a growing engineering organization of approximately 40 engineers across several squads, managing a small group of Engineering Managers and senior technical leaders. You will partner closely with Product, Data, and Commercial leadership to translate ambitious product goals into scalable technical systems and high‑impact engineering roadmaps.

This role is ideal for a hands‑on technical leader who still enjoys being close to the code and architecture. While you won’t be coding day‑to‑day, you will regularly participate in architecture discussions, code reviews, and technical decision‑making, ensuring the team maintains high technical standards while moving quickly. You will own the engineering roadmap and technical strategy, working across squads to balance new product development with platform health, scalability, and long‑term technical investments.

As a leader of leaders, you will focus on building strong engineering management practices, developing senior talent, and fostering a culture of innovation, ownership, and operational excellence.

Engineering

Leadership & Team Development Lead and scale a high‑performing engineering organization of approximately forty engineers across multiple squads, with explicit expectations on quality, ownership, collaboration, and speed. Evolve the engineering org structure (squads, platform vs product, EM layer, TLs, Staff/Principal roles) as the company scales. Own the engineering hiring bar and process, especially for senior talent.

Implement robust performance, feedback, and growth processes that are fair,



transparent, and aligned with company values. Address misalignment or under‑performance at all levels with clarity and empathy. Build strong engineering management practices, including performance calibration processes, career development frameworks, and leadership mentorship.

Foster a culture of ownership, technical excellence, and continuous improvement across the engineering organization. Build a strong succession pipeline for critical roles (Tech Leads, Engineering Managers, Staff Engineers).

Technical

Strategy & Roadmap Ownership Define and communicate a clear engineering strategy and roadmap that supports company‑level outcomes (revenue, margins, product bets, and tech sustainability). Translate business goals into concrete technical portfolios (new product, platform, productivity, and KTLO). Drive long‑term investments in platform scalability, developer productivity, technical debt reduction, and infrastructure reliability.

Continuously refine engineering metrics (e.g., Own the long‑term evolution of our technical architecture across backend services, AI systems, browser technology, and cloud infrastructure. Remain hands‑on enough to participate in code reviews, architecture reviews, and key technical decisions. Be accountable for the quality of our products and services.

Partner closely with Product, Data, and Commercial leadership to align engineering execution with company priorities. Lead technical intake processes across departments to ensure engineering resources are focused on the highest‑impact initiatives. Translate business goals into transparent technical strategies and engineering priorities.

Work with Security and Legal on security programs, privacy, and compliance (e.g.,



Platform & Engineering Excellence Oversee the health and scalability of Stay22’s core platform, including backend services, data pipelines, and hub. Ensure the engineering organization maintains high standards for security, privacy, and system reliability. Champion engineering tooling, development workflows, and operational improvements that increase team productivity and platform quality.

Drive cross‑squad initiatives that improve the effectiveness and cohesion of the engineering organization. Align technical strategy with the company’s growth plans and product vision. Act as a key technical voice within the leadership team, contributing to broader company strategy and decision‑making.

English proficiency required for daily communication with international colleagues and team members. ~15+ years of experience in software engineering, with significant experience building scalable systems and platforms. ~5+ years of experience in engineering leadership, including managing managers and leading multi‑team engineering organizations. ~ Track record as Head of Engineering or VP Engineering in a B2B SaaS, marketplace, or ad/affiliate‑driven environment. ~ Strong technical background in modern backend systems, including JavaScript/TypeScript, Node.js, and Python. ~ Demonstrated ability to review architecture, guide technical decisions, and maintain credibility with senior engineers and staff‑level developers. ~ Experience defining and tracking engineering performance metrics (e.g., Strong cross‑functional leadership skills, with the ability to collaborate effectively with Product, Data, and business leadership. ~ Demonstrated ability to re‑prioritize engineering portfolios in response to business shifts and align stakeholders around those choices. ~ Comfortable working closely with executive leadership, board‑level stakeholders, and cross‑functional peers. Technical discussion with the co‑founder (60 minutes). # In‑office panel with team members (45‑60 minutes). # Support travel creators to generate more revenue. Bright office in the heart of Little Italy.

Flexible schedule and relaxed atmosphere. Health, dental, retirement, and training benefits, plus team activities.

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