About Stay22

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. At Stay22, our partners don’t just earn more, they deliver more. Join us and be part of something big that's shaking up the affiliate world.

Position overview

We are seeking an energetic and experienced Senior Technical Engineering Manager to lead our Phantom and Social Affiliate squads. In this role, you will manage a talented combined team of 5-8+ engineers with diverse profiles, driving execution and delivery across both teams. You will balance people leadership with hands-on technical work - roughly 20% of your time will involve diving into code reviews, architecture discussions, and even coding small features or fixes. This hands-on involvement is critical for maintaining credibility and providing effective mentorship to engineers working on highly specialized and distinct technical challenges.

Working closely with two Product Managers, you'll translate an ambitious roadmap into actionable plans and guide your teams to deliver high-impact, scalable solutions. Reporting directly to our Head of Engineering, you will be a key member of the engineering leadership team - coaching and growing your engineers, unblocking complex technical challenges, and ensuring our platform's services are robust, scalable, and high-quality.

Key responsibilities

• Build and manage a high-performing, blended team of engineers across the Phantom and Social Affiliate squads, fostering a culture of collaboration, innovation, and continuous improvement
• Adapt your leadership style to mentor and grow two distinct engineering profiles: deep systems specialists in Phantom focused on browser internals, and full-stack product engineers in Social Affiliate focused on AI applications and user workflows
• Lead Agile ceremonies (sprint planning, stand-ups, retrospectives, and incident post-mortems) for your teams, continuously improving team workflows, communication, and productivity
• Encourage a culture of innovation by identifying opportunities to leverage new technologies or process improvements that could elevate our platform, championing these initiatives from concept to implementation
• Supervise the development of automated pipelines using Python on GCP and leveraging LLMs to analyze video content and identify affiliate opportunities
• Guide the team in integrating with the Social platform APIs to retrieve and programmatically update video content, metadata, and transcripts.
• Collaborate closely with the Hub team to design and implement seamless, user-facing workflows for social integrations, including UI components for linking accounts, reviewing analytics, and managing content
• Oversee the end-to-end execution of projects, ensuring the timely delivery of features that meet quality standards and align with the goal of turning social content into commission-generating assets for creators
• Set the technical direction for the company's browser-level infrastructure, leading architecture and design reviews for script lifecycle performance, DOM automation and iframe swapping strategies.
• Lead critical technology decisions regarding privacy-conscious browser fingerprinting, session management techniques, and user identification systems that respect evolving standards
• Ensure the health and scalability of core services by implementing best practices in testing, monitoring, and alerting. Proactively address tech debt and performance bottlenecks in our embedded scripts and networking pipelines
• Remain actively involved in the codebase by conducting thorough code reviews, guiding architectural decisions, and occasionally writing code for critical features or bug fixes (approximately 20% of your time)
• Collaborate closely with Product Managers and other stakeholders to refine requirements, prioritize roadmaps, and ensure engineering efforts are aligned with business goals
• Act as the main point of contact for your teams when communicating with senior leadership. Regularly update the Head of Engineering on project status, technical decisions, and team progress, proactively managing expectations and surfacing risks
• Manage key "X-as-a-Service" relationships with other engineering squads, such as providing browser-handling libraries to EmbedX, integrating with Neuro’'s redirect logic, and supplying performance data to the Data team

Requirements

• Bachelor's or Master's degree in Computer Science, Software Engineering, or a related field (or equivalent experience)

• 8+ years of experience in software development, with a track record of building scalable, reliable systems. At least 4+ years in an engineering leadership or management role, leading teams to deliver complex projects

• A strong technical background in both domains. You are equally comfortable and credible discussing:

  • Application & AI Systems: Modern backend development (Python preferred, Node.js), cloud platforms (GCP), building and deploying AI/ML solutions (especially using LLMs), and integrating with third-party APIs
  • Low-Level Web & Browser Technologies: Deep expertise in JavaScript/TypeScript, browser performance optimization, DOM manipulation, browser security models, and networking protocols

• Proven ability to lead, coach, and develop diverse engineering teams. You excel at mentoring developers with different specializations, from systems engineers to product-focused generalists, providing constructive feedback and helping individuals grow in their careers

• Excellent communication and interpersonal skills. Comfortable collaborating with cross-functional teams (Product, Design, other Engineering squads) and translating complex technical details into clear, actionable insights for stakeholders

• Creative and pragmatic problem-solver with a knack for navigating complex technical challenges. Able to make sound architectural decisions that balance immediate product needs (Social Affiliate) with long-term platform health and scalability (Phantom)

• Demonstrated experience balancing hands-on technical involvement with high-level leadership. You take ownership of outcomes, ensure high quality standards, and have a track record of driving projects to successful completion. Experience in a fast-paced, agile startup/scale-up environment is highly valued

What to Expect from our Hiring Process

We know your time’s valuable, so here’s the quick rundown of what to expect.

• Screening call with our Talent Acquisition Partner (30-45 minutes)
• Whiteboarding session oriented on System Design (Miro) with the Head of Engineering (90 minutes)
• Final interview with our CEO (30 minutes)
• Offer & onboarding

Please note that this process is subject to change at any point, based on additional requirements from the team.

Why join Stay22?

• Support Travel Creators: Be part of a team that empowers travel creators to explore the world by increasing their passive income potential.
• Empower Your Growth: We hire champions and give them the opportunity to excel, skipping levels and honing their superpowers.
• Lead with Impact: We empower our team members to take charge and make a real impact in the Stay22 universe.
• Location, Location, Location: Enjoy our bright and vibrant office in the heart of Montreal’s Plateau Mont-Royal, surrounded by the best shops and restaurants
• Be Yourself: Embrace a come-as-you-are dress code and a flexible work schedule.
• Comprehensive Benefits: We offer health & dental benefits, retirement plans, learning & development opportunities, and social & team-building activities, including exciting retreats.

(Stay22 is an equal-opportunity employer. All qualified applicants are given consideration. If you have a disability or particular need that requires accommodation, please contact us at careers at stay22.com*)*