What we do: We connect people with well-planned, unforgettable travel experiences.
How we do it: We’re an agile team whose mantra says it all; Think Big. Start Small. Move Fast.
Travelstride is an ambitious Venture-funded Seed stage startup led by industry & tech veterans that is serving a large, growing opportunity. Our investors include JetBlue Ventures, NFX (top VC for marketplaces), New York Angels, Sand Hill Angels, and the founders of Trulia, Get There, Hipmunk, TripIt, and Google Now.
Travelstride is the #1 US platform for experiential trips, powered by a combination of AI and a local expert network. We are building the future of vacation planning. With over 350,000 trusted reviews, we are aiming to become the go-to community for curious travelers.
As the top marketplace for tours, tailor-made vacations, and adventure trips, our platform hosts more than 50,000 itineraries across every continent crafted by the world’s best trip designers.
Travelstride utilizes GenAI in an innovative way giving travelers the ability to easily create personalized, bookable trips. With the customizable magic of AI combined with a local expert to refine and book the itinerary, the customer can plan delightfully and travel with confidence.
We are a values and mission driven company. While many say it, we live it daily, and encourage you to review our core values and our careers page to see if we are a good mutual fit.
Our MISSION: Cultivate a community connecting travelers with extraordinary places, people and experiences.
Our MANTRA: Think big. Start Small. Move fast. First, do it. Then do it right. Then do it better.
The Role in One Line:
Lead and grow a team of 6 software engineers as the chief technical architect to collaborate with business leaders to build and scale an innovative AI-driven 21st century travel platform.
Overview:
Travelstride is seeking an entrepreneurial and hands-on CTO to lead our engineering team and drive the evolution of our technology stack as we scale. The CTO will be critical in aligning our technical solutions with the company's strategic goals, ensuring that our platform remains innovative, robust, scalable, and efficient as we expand. You will report to the CEO and founder and collaborate closely with the heads of Product, Marketing, Sales, Partnerships, and Customer Success. Our core system is build in Python/FastAPI with parts of older platform in Ruby on Rails. This role is ideal for someone who thrives in a dynamic startup environment, loves solving complex problems, and is passionate about early stage startups, marketplaces, AI, and travel.
Key Responsibilities:
Technology Leadership (50%)
Lead by example, spending approximately 50% of your time as an individual contributor, writing code and solving the most challenging technical problems.
Architect and design a platform that is scalable, secure, and can support the complex needs of our marketplace, including international payments, multi-language support, data integration, and closed-loop messaging systems.
Integrate emerging technologies, including Generative AI, into the platform to enhance user experience, streamline internal processes, and provide personalized travel recommendations.
Ensure the system is built for scalability, security, and high performance, applying DevOps best practices.
Stay ahead of industry trends, continuously evaluating new tools and technologies that could enhance our platform’s performance or user experience.
Team Management & Coaching (25%)
Lead and mentor a team of 6 engineers, helping them grow their technical abilities while fostering collaboration, innovation, and continuous improvement.
Set clear goals for the engineering team, conducting regular reviews, and providing feedback to ensure high standards and personal development.
Foster a growth mindset within the team and drive best practices in software engineering, including code reviews, agile processes, and project planning.
Business Collaboration & Stakeholder Engagement (25%)
Work closely with the CEO, Product Manager, UX Designer, and leadership team to ensure technology strategies align with company goals and user needs.
Collaborate with the product team to align tech with business objectives, ensuring product features align with strategic goals for users and B2B partners.
Interface with Sales and Marketing to understand customer feedback and market needs, translating these into technical solutions and improvements.
Collaborate with key B2B partners, investors, and other external stakeholders, ensuring our tech meets their needs and fostering productive relationships.
Key Technical Challenges to Address:
GenAI Integration: Drive the next stage of our leveraging Generative AI technologies to improve user experience, personalize recommendations, optimize revenue and differentiate from competitors.
International Payments: Lead the development and implementation of a robust international payments system.
Multiple Languages & Globalization: Architect the platform to support multi-language, multi-currency, and international requirements.
3rd Party APIs & Data Integration: Build scalable solutions to aggregate and manage data from multiple sources, including third-party APIs and screen scraping.
Closed-Loop Messaging: Develop a secure, efficient messaging system for communication between travelers, trip planners, and other marketplace participants.
Security & Compliance: Ensure the platform meets the highest standards for security, privacy, and industry-specific regulations.
DevOps & Scaling Architecture: Lead the design of cloud architecture to support rapid scaling while maintaining system stability and reliability.
About You:
You love tech and software, and enjoy experimenting with new tools and approaches.
You’re passionate about AI and have crafted your own experiments for fun and work.
You wake up excited to write code and dive into solving challenging technical problems.
You obsess over writing high-quality code and think about process and scale.
You’re eager to lead and create a technology platform that integrates payments, messaging, and cutting-edge AI.
You enjoy collaborating with business leaders to translate user and company goals into innovative solutions and products.
You are energized by the idea of managing other engineers, creating an effective team culture, and coaching individual engineers to reach peak performance.
Your ideal workday includes 50% coding, 25% engineering team collaboration, and 25% business strategy discussions and collaboration.
Requirements:
5+ years of experience in software development
Proven experience in architecting and scaling complex, global platforms, particularly in marketplaces, e-commerce, or consumer internet businesses.
Expertise with agile dev methodologies and silicon valley startup best practices.
Strong hands-on experience with full-stack development, APIs, cloud infrastructure, and security best practices.
Experience leading teams, not necessarily as an engineering manager, mentoring devs.
Excellent communication skills - can explain complex technical concepts to non-experts.
A track record of aligning technical strategies with business goals and driving innovation.
History of integrating new technologies, including Generative AI, in live environments.
‘Nice to Have’ Qualifications
:
Experience managing direct reports
Know payment systems, data integration, security, and messaging protocols.
Experience in the travel or e-commerce industry, particularly with marketplaces.
Bachelor's or Master’s degree in Computer Science, Engineering, or a related field
To Apply:
Please send your resume and a cover letter outlining why you're a great fit for this role, which of our core values resonate most and least with you, and your most relevant, impressive accomplishment.
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