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 Dating Coach to work with clients looking to improve their dating lives and build meaningful connections. This role includes helping clients with general exploration of their dating goals and identifying relationship goals, as well as building confidence and conversation skills. Coaches also support clients with dating profile review & optimization, messaging strategy, and date planning & preparation, along with post-date debrief & analysis to help clients learn and grow from each experience. Ideal candidates have hands-on experience coaching others through dating and relationships (as a dating coach, matchmaker, or related professional), a strong understanding of modern dating dynamics, and a clear, structured approach to helping clients build confidence and real connection. 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.