VP of Engineering

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead and cultivate a streamlined, senior engineering team.

• Foster a robust engineering culture, create growth pathways, mentor engineers into leadership roles, and make performance-related decisions when coaching proves ineffective.

• Recruit talent based on judgment and expertise, including assessing candidates' proficiency in AI.

• Manage a remote, written, asynchronous work culture with clearly defined ownership.

• Identify opportunities where coding agents and LLM tools enhance product, design, and engineering processes.

• Evaluate AI-tool return on investment through cycle time, defect rates, and cost; establish quality and security standards.

• Guide product, design, and engineering teams on effective agent implementation and phase out inefficient workflows.

• Enhance delivery speed through CI/CD practices, automated testing, observability, feature flagging, and experimentation.

• Define technical strategy and architecture for the codebase and data pipeline.

• Ensure data-pipeline accuracy, timeliness, and cost-effectiveness as the company grows.

• Address technical debt where it adds business value.

• Collaborate with Product and Data teams to create AI-driven member experiences before and after bookings.

• Provide technical leadership while maintaining technical credibility.

• Work alongside the Leadership Team, Product, Marketing, Operations, and Data divisions.

• Align engineering roadmap decisions with membership growth objectives.

• Report directly to the CEO.

⛳️ Requirements

• You must be legally authorized to work in the United States and available to work during US hours.

• Over 10 years of experience in software, including more than 5 years leading engineering teams of 8–25 in a consumer tech company, ideally in a startup or scale-up environment.

• Regular use of coding agents and LLM tools; understanding their benefits, limitations, and output verification processes.

• Proven experience in leading AI-tool adoption that resulted in measurable improvements without mandates or compromising quality.

• Product-centric mindset focused on member and customer value.

• Ability to deliver, learn, iterate, and make reversible decisions swiftly.

• Experience in building reliable, high-traffic consumer systems, including iOS and Android applications, while handling large and complex datasets.

• Proficient in hiring, providing direct feedback, and mentoring engineers into leadership positions.

• Strong written communication skills and capability to manage an asynchronous remote team, explaining technical trade-offs to non-engineers.

• A security- and privacy-focused approach to member data and payment processes.

• Preferred experience in flights or travel, airfare data, GDSs, NDC, metasearch, OTAs, or airline retailing.

• Preferred experience in developing agentic or LLM-powered consumer-product features.

• Preferred experience with pricing, alerting, or real-time data pipelines.

• Preferred experience in subscription or membership-based businesses.

• Preferred experience in leading an engineering organization through significant tooling or process changes.

🏝️ Benefits

• Equity

• 100% remote work environment

• Annual team retreats

• Open vacation policy, with a minimum of 15 days

• Comprehensive health, vision, dental, and life insurance

• 401(k) plan with a 5% match

• $750 quarterly stipend for remote work, wellness, and personal development

• Up to 12 weeks of paid family leave

• Meetup stipend when you encounter a co-worker

• Continuing education and development reimbursement