Engineering Manager | Scrabble & Jigsaw
full-time
Posted on May 19, 2026
Job Description
Engineering Manager
Company Overview
Headout is a rapidly growing marketplace in the travel industry, generating $130 million in revenue with record growth and profitability. With a presence in over 100 cities and having raised $60 million+ from top-tier investors, Headout is committed to enhancing human experiences by facilitating real-life interactions through immersive tours, museums, live events, and more.
Job Summary
As an Engineering Manager at Headout, you will lead a product engineering team focused on creating consumer-facing experiences. You will balance technical excellence with product thinking, guiding your team to deliver high-quality and scalable user experiences for millions of travelers worldwide.
Responsibilities
- Lead and mentor a team of engineers, making critical architectural and system design decisions.
- Own the outcomes of key product initiatives, focusing on customer impact and business results.
- Build products that enhance discovery, conversion, retention, and overall customer experience.
- Collaborate with product, design, and data teams to create intuitive and high-performing user experiences.
- Drive end-to-end execution of critical initiatives while maintaining autonomy over technical and team decisions.
- Recruit, develop, and retain top engineering talent, fostering a culture of craftsmanship and continuous learning.
- Innovate using modern technologies to tackle evolving product challenges across scalability and performance.
- Participate in developing products for a global audience, enhancing experiences across diverse markets.
Qualifications
- Experience: A minimum of 7 years in software development, with at least 2 years in an engineering leadership role.
- Technical Skills: Proficiency in system design, architecture, and both frontend and backend development, with hands-on experience in cloud technologies (AWS, GCP, or Azure).
- Product and Engineering Alignment: Ability to link engineering decisions to product goals and customer experiences.
- Problem-Solving: Exceptional skills with a focus on scalability, performance optimization, and engineering quality.
- Cross-Functional Collaboration: Experience working with product, design, analytics, and business teams to deliver impactful experiences.
- Communication: Strong skills in articulating technical trade-offs and decisions clearly.
- Mentorship: A passion for mentoring engineers while promoting an inclusive and high-performing culture.
- Education: Relevant degree in Computer Science, Engineering, or a related field is preferred.
Preferred Skills
- Experience with modern engineering practices and methodologies.
- Understanding of user journeys, conversion funnels, and customer behavior analytics.
- Familiarity with performance measurement and experimentation techniques.
Experience
- Minimum of 7 years of experience in software development, with at least 2 years in leadership roles.
Environment
- Work within a dynamic and innovative environment that encourages solving tough problems. Opportunities to collaborate with a globally distributed team.
Salary
- Not specified.
Growth Opportunities
- Opportunities to drive innovation and lead pivotal projects, enhancing your career growth within a key player in the travel industry.
Benefits
- Not specified.
