Leland

Travel Planning Coach

Remote, United States remote Entry Salary not listed
remote Technology & IT Curated
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About the role

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.
Originally posted on Himalayas

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Role
Technology & IT Writing Travel Planning Coach Technology remote

Likely questions

  1. Tell us about work you have done that is close to the Travel Planning Coach role.
  2. How would you approach your first 30 days at Leland?
  3. Which of Writing, Travel and Planning have you used recently, and what did it help you achieve?
  4. Describe a time you solved a problem without waiting to be told exactly what to do.
  5. How do you stay organised and communicate clearly when working remotely?

Prepare before the call

  • A recent example that proves your experience with Writing, Travel and Planning.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Travel Planning Coach role because I can bring practical experience in Writing, Travel and Planning, learn the team quickly, and contribute to the outcomes Leland needs from this hire.

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