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About This Role
KAYAK, part of Booking Holdings (NASDAQ: BKNG), is a leading travel search engine. With billions of queries across our platforms, we help people find their perfect flight, stay, rental car and vacation package. We’re also transforming business travel with a new corporate travel solution, KAYAK for Business.
As an employee of KAYAK, you will be part of a travel company that operates a portfolio of global metasearch brands including momondo, Cheapflights and HotelsCombined, among others. From start-up to industry leader, innovation is in our DNA and every employee has an opportunity to make their mark. Our focus is on building the best travel search engine to make it easier for everyone to experience the world.
We are looking for a strong Java Senior Software Engineers to implement new features and maintain KAYAK’s AI. You will be an essential part of a high powered team that keeps all of this running smoothly – helping millions of people find the best hotels and the best ways to fly from A to B every day!
This role requires commuting to the Concord, MA office 3 times a week.
In this role, you will:
- Design, implement and maintain reliable production software for KAYAK’s travel-search and trip-planning experiences.
- Build and evolve APIs and services supporting AI-assisted search, conversational travel planning, itineraries and related user experiences.
- Investigate technical problems, assess trade-offs and choose practical solutions that improve reliability, performance and maintainability.
- Write automated tests and contribute to quality across unit, integration and end-to-end testing.
- Participate in code reviews and technical discussions, providing constructive feedback focused on correctness, clarity and maintainability.
- Work with engineers, product managers and designers to clarify requirements and deliver useful, accessible user experiences.
- Contribute to features such as ASK AI, smart filters, AI-generated hotel review summaries, Explore and related search experiences.
- Help make AI-assisted features dependable, transparent and useful to travelers.
- Learn unfamiliar systems and share knowledge with teammates through documentation, pairing and technical discussions.
- Monitor and improve production behavior through effective debugging, observability and root-cause analysis.
- Contribute to the evolution of development tools, engineering processes and delivery practices.
Please apply if you have:
- Experience building and maintaining production software.
- Proficiency in Java or another relevant programming language.
- Familiarity with APIs, data structures and software-design principles.
- Experience testing software and investigating defects or production issues.
- The ability to explain technical decisions clearly in writing and conversation.
- The ability to take ownership of assigned work while asking for input or support when needed.
- Experience contributing to projects from design through implementation, release and maintenance.
- Equivalent practical experience is welcome in place of a specific degree or educational path.
The following will help you stand out:
- Experience with distributed systems, search, personalization or other high-volume consumer products.
- Experience with AI, machine learning or large language model applications.
- Experience with relational databases or other structured data stores.
- Experience working on web products, mobile products or travel-related products.
- Experience improving accessibility, reliability or usability.
- Experience working with Java and Spring.
- Experience with cloud services, CI/CD pipelines and automated testing frameworks.
Benefits and Perks
- Work from (almost) anywhere for up to 20 days per year
- Focus on mental health and well-being:
+ Company-paid therapy sessions through SpringHealth + Company-paid subscription to HeadSpace + Company-wide week off a year - the whole team fully recharges (and returns without a pile-up of work!) + No meeting Fridays + Paid parental leave + Generous paid vacation + time off for your birthday + Paid volunteer time
- Focus on your career growth:
+ Development Dollars + Leadership development + Access to thousands of on-demand e-learnings
- Travel Discounts
- Employee Resource Groups
- Competitive retirement and health plans
- Free lunch 2 days per week
- Fun quarterly events such as boat trips, arcades, ski trips, Thursday happy hours, and more
Compensation
There are a variety of factors that go into determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required. The range for this Massachusetts based role is $160,000-180,000, not inclusive of annual bonus and recurring RSU grants.
We offer a competitive base salary and benefits including: health benefits; flexible spending account; retirement benefits; life insurance; paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays and paid holidays); and parental leave benefits.
Inclusion
At KAYAK, we want everyone to have the space to grow, share ideas and do great work. That's why we're focused on hiring the best talent from all walks of life and experiences, supporting them well and making sure no one feels like they have to fit a mold to belong here.
Need any adjustments for the interview, application or on the job? No problem – just give us a heads-up. We've got you.
#LI-AS1
Salary Context
This $160K-$180K range is below the median for AI Software Engineer roles in our dataset (median: $192K across 146 roles with salary data).
Role Details
About This Role
AI Software Engineers build the applications and systems that AI models run inside. They own the API layers, data pipelines, frontend integrations, and infrastructure that turn a model into a product users interact with. Every AI company needs engineers who can build the software around the AI.
The challenge is building reliable systems around inherently unreliable components. Models are probabilistic. They'll give different answers to the same question. They hallucinate. They're slow. They're expensive. Your job is to build an application layer that handles all of this gracefully while delivering a product that users trust and enjoy.
Across the 8,943 AI roles we're tracking, AI Software Engineer positions make up 4% of the market. At KAYAK, this role fits into their broader AI and engineering organization.
AI Software Engineer roles are among the most numerous in the AI job market. Every company deploying AI needs software engineers who understand AI integration patterns. The demand is broad, spanning startups to enterprises, across every industry adopting AI capabilities.
What the Work Looks Like
A typical week includes: building API endpoints that serve model inference with caching and fallback logic, designing the data pipeline that feeds context to a RAG system, implementing streaming responses in the frontend, debugging a race condition in the async inference pipeline, and optimizing database queries for the vector search layer. It's full-stack engineering with AI at the center.
AI Software Engineer roles are among the most numerous in the AI job market. Every company deploying AI needs software engineers who understand AI integration patterns. The demand is broad, spanning startups to enterprises, across every industry adopting AI capabilities.
Skills Required
Full-stack engineering skills with AI integration experience. Python and TypeScript are the most common requirements. You'll need to understand API design, database architecture, and how to build reliable systems around probabilistic outputs. Experience with streaming, async processing, and caching patterns is increasingly important as real-time AI applications proliferate.
Knowledge of vector databases, embedding APIs, and LLM integration patterns (function calling, structured outputs, retry logic) differentiates AI software engineers from general software engineers. Understanding cost optimization (caching strategies, model routing, batched inference) is valuable since inference costs can dominate application economics.
Strong postings describe the product you'll be building, the AI integration patterns you'll work with, and the scale requirements. Look for companies that have existing AI features and need engineers to improve and expand them, not companies that are 'planning to add AI' someday.
Compensation Benchmarks
AI Software Engineer roles pay a median of $220,000 based on 1,448 positions with disclosed compensation. Senior-level AI roles across all categories have a median of $228,700. This role's midpoint ($170K) sits 23% below the category median. Disclosed range: $160K to $180K.
Across all AI roles, the market median is $213,380. Top-quartile compensation starts at $264,148. The 90th percentile reaches $319,310. For comparison, the highest-paying categories include AI Safety ($253,100) and Research Engineer ($252,000). By seniority level: Entry: $110,408; Mid: $193,200; Senior: $228,700; Director: $272,250; VP: $235,000.
KAYAK AI Hiring
KAYAK has 1 open AI role right now. They're hiring across AI Software Engineer. Based in Concord, MA, US. Compensation range: $180K - $180K.
Location Context
Across all AI roles, 6% (521 positions) offer remote work, while 8,351 require on-site attendance. Top AI hiring metros: New York (2,878 roles, $221,000 median); San Francisco (2,416 roles, $263,811 median); Los Angeles (1,340 roles, $210,000 median).
Career Path
Common paths into AI Software Engineer roles include Software Engineer, Full-Stack Developer, Backend Engineer.
From here, career progression typically leads toward Staff Engineer, AI Architect, Engineering Manager.
If you're a software engineer, you're already 80% there. Learn the AI integration patterns: RAG, streaming inference, function calling, structured outputs. Build a project that demonstrates you can wrap an AI model in a production-quality application with proper error handling, caching, and user experience. That's the portfolio piece that gets you hired.
What to Expect in Interviews
Technical screens look like standard software engineering interviews with an AI twist. Expect system design questions about building reliable applications around probabilistic models: handling streaming responses, implementing retry logic for API failures, and designing caching strategies for LLM outputs. Coding rounds test standard algorithms plus practical integration patterns like async processing and rate limiting.
When evaluating opportunities: Strong postings describe the product you'll be building, the AI integration patterns you'll work with, and the scale requirements. Look for companies that have existing AI features and need engineers to improve and expand them, not companies that are 'planning to add AI' someday.
AI Hiring Overview
The AI job market has 8,943 open positions tracked in our dataset. By seniority: 175 entry-level, 4,132 mid-level, 3,268 senior, and 1,368 leadership roles (Director, VP, C-Level). Remote roles make up 6% of the market (521 positions). The remaining 8,351 roles require on-site or hybrid attendance.
The market median for AI roles is $213,380. Top-quartile compensation starts at $264,148. The 90th percentile reaches $319,310. Highest-paying categories: AI Safety ($253,100 median, 57 roles); Research Engineer ($252,000 median, 419 roles); AI Engineering Manager ($251,622 median, 51 roles).
AI Software Engineer roles are among the most numerous in the AI job market. Every company deploying AI needs software engineers who understand AI integration patterns. The demand is broad, spanning startups to enterprises, across every industry adopting AI capabilities.
The AI Job Market Today
The AI job market spans 8,943 open positions across 16 role categories. The largest categories by volume: AI/ML Engineer (6,739), AI Product Manager (403), AI Software Engineer (402). These three account for the majority of open positions, though smaller categories often have higher per-role compensation because of specialized skill requirements.
The seniority mix tells a story about where AI teams are in their maturity. Entry-level roles (175) are outnumbered by mid-level (4,132) and senior (3,268) positions, reflecting that most companies are past the 'build a team from scratch' phase and need experienced engineers who can ship production systems. Leadership roles (Director, VP, C-Level) total 1,368 positions, representing the bottleneck between technical execution and organizational strategy.
Remote work availability sits at 6% of all AI roles (521 positions), with 8,351 requiring on-site or hybrid attendance. The remote share has stabilized after the post-pandemic correction. Senior and specialized roles (Research Scientist, ML Architect) are more likely to be remote-eligible than entry-level positions, partly because experienced hires have more negotiating power and partly because these roles require less hands-on mentorship.
AI compensation is structured in clear tiers. The market median sits at $213,380. Top-quartile roles start at $264,148, and the 90th percentile reaches $319,310. These figures include base salary with disclosed compensation. Total compensation (including equity, bonuses, and sign-on) runs 20-40% higher at companies that offer those components.
Category matters for compensation. AI Safety roles lead at $253,100 median, while Prompt Engineer roles sit at $141,440. The spread between highest and lowest-paying categories reflects the premium on specialized technical skills versus broader analytical roles.
The most in-demand skills across all AI postings: Python (1,422 postings), Aws (808 postings), Azure (638 postings), Rag (555 postings), Gcp (457 postings), Pytorch (433 postings), Claude (341 postings), Kubernetes (337 postings). Python dominates, appearing in the vast majority of role descriptions regardless of category. Cloud platform experience (AWS, GCP, Azure) is the second most common requirement. The newer entrants to the top skills list (RAG, vector databases, LLM APIs) reflect the shift from traditional ML toward generative AI applications.
Frequently Asked Questions
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