Leland is building the home for ambition in the age of AI. We connect people with the experts, programs, and communities they need to land the job, get into the school, or upskill for a world being rewritten by AI. We help businesses become AI-native through training, hiring, and infrastructure. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals and raised $19M from world-class investors. Ambition is sacred to us, and we've built a product that takes that seriously.

We're seeking an experienced travel planning coach to work with clients looking to plan smarter, more rewarding trips, as well as aspiring travel planners looking to break into the profession. This role includes general exploration to help clients clarify their travel goals, as well as destination research and selection and itinerary planning tailored to their interests and timeline. Coaches also guide clients through budget planning, booking strategy for flights and accommodations, and travel hacking using points and miles to stretch their travel budget further, along with visa and documentation guidance for international trips. For those pursuing travel planning as a career, coaches provide skill building, guidance on freelancing and building a client base, and support with resume review, interview prep, and networking strategy to help them break into the industry. Ideal candidates have extensive personal travel experience or professional travel planning experience, prior coaching or mentoring experience, and a clear, structured approach to helping clients plan trips and aspiring planners grow their careers. Coaches set their own hours and rates, host sessions virtually, and partner with our team to deliver a high-quality, supportive experience for every client.

Why Leland?

• The chance to join a world-class team helping people achieve their career and educational dreams

• Work in a collaborative, high-energy environment where your contributions have a direct impact

• Operate in a fast-paced, AI-native environment

• We don't hire people who merely want to work for a great company; we hire people who want to make a great company

Leland is an equal opportunity employer. We encourage candidates of all backgrounds and demographics to apply.