Customer Success Coach

Leland; United States; Remote; USD 60,000 - 85,000; Full time

Job summary

Leland is seeking an experienced Customer Success Coach to guide clients into and within customer success roles, teaching onboarding, strategy, and relationship management. Coaches tailor sessions to build retention, satisfaction, and feedback analysis practices, while leveraging AI fundamentals and automation in client work.

As a remote, self-directed role, you’ll set your hours and rates, host sessions virtually, and collaborate with our team to deliver a high‑quality coaching experience for

Qualifications

• Hands-on experience in customer success roles (CSM, AM, or equivalent).
• Strong track record of driving customer outcomes and retention.
• Clear, structured approach to coaching clients through technical and career growth.

Responsibilities

• Teach core customer success strategy, onboarding, and relationship management.
• Help clients strengthen retention, satisfaction, and feedback analysis practices.
• Guide clients on applying AI fundamentals and AI automation to customer success work.
• Provide resume review, LinkedIn review, cover letter guidance, interview prep, networking strategies, and salary/promotion guidance.

Skills

Customer Success

Coaching

Career coaching

Relationship management

Tools

CRM software

Video conferencing

Job description

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 Customer Success Coach to work with clients looking to break into or grow within customer success roles. This role includes teaching core customer success strategy, customer onboarding, and customer relationship management skills, as well as helping clients strengthen customer retention, customer satisfaction, and customer feedback analysis practices. Coaches also guide clients on applying emerging tools like AI fundamentals and AI automation to their customer success work. On the career side, coaches offer resume review, LinkedIn review, and cover letter guidance, plus interview prep, networking strategy, salary negotiation, and promotion strategy tailored to customer success roles, along with broader skill building. Ideal candidates have hands‑on experience in customer success (as a customer success manager, account manager, or industry professional), a strong track record of driving customer outcomes and retention, and a clear, structured approach to coaching clients through both technical and career growth. 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.