[Hiring] Customer Success Specialist @Sketchy

Role Description

Sketchy is looking for a Customer Success Specialist to support our institutional customers throughout onboarding, adoption, ongoing engagement, and renewal preparation. Reporting to the Institutional Customer Success Manager, you’ll serve as a day-to-day resource for MD, DO, PA, NP, RN, and GME programs. You’ll coordinate training, monitor usage, prepare reports, manage follow-up, and maintain customer records to help institutions use Sketchy effectively. You’ll work with Sales, Marketing, Product, Support, and other internal partners to resolve customer questions, share feedback, and support retention and renewal preparation.

Sketchy is hiring remote employees in these select US states: California, Colorado, Florida, Illinois, Massachusetts, Michigan, New Jersey, New York, Pennsylvania, Texas, Utah, and Washington!

Responsibilities

• Customer Relationship Management:
  • Support a portfolio of institutional accounts by responding to customer questions, conducting regular check-ins, and coordinating follow-up to help maintain strong engagement and satisfaction.
  • Escalate strategic or leadership-level issues to the Institutional Customer Success Manager.
• Onboarding, Training & Adoption:
  • Support new client onboarding, account setup, implementation, training, and ongoing education.
  • Provide resources and best practices that help customers use Sketchy effectively.
• Learner & Educator Support:
  • Respond to and triage student and faculty support requests.
  • Escalate technical issues to the Support team and track recurring questions.
• Usage, Reporting & Account Health:
  • Monitor customer usage and engagement and prepare customer-facing reports and presentations.
  • Identify accounts that may benefit from additional outreach or support.
• Renewals & Growth Support:
  • Partner with Sales and the Institutional team on renewal preparation, retention initiatives, and account planning.
  • Help identify potential expansion opportunities.
• Voice of the Customer & Issue Resolution:
  • Gather and document customer feedback and coordinate with Product and Support to resolve issues.
  • Identify recurring questions or challenges that may inform improvements to the product, resources, or customer experience.
• CRM, Documentation & Cross-Functional Coordination:
  • Maintain accurate customer records and activity in CRM and Customer Success systems, such as HubSpot.
  • Coordinate institutional communications, resources, and related initiatives with Sales, Marketing, Product, Support, and other internal partners.
• AI-Assisted Customer Success:
  • Use approved AI tools to support meeting notes, follow-up drafting, customer resource preparation, summarization, and routine account administration.
  • Validate AI outputs and protect customer information.

Qualifications

• 1–3 years of experience in Customer Success, Account Management, Client Services, Customer Support, Education, SaaS, or a related customer-facing role.
• Bachelor’s degree in Business, Communications, Education, or a related field, or equivalent relevant experience.
• Basic proficiency with AI tools for prompting, summarization, drafting, research, or routine workflow support, with the ability to validate outputs and follow company data and privacy guidelines.
• Ability to travel up to 1-2 times per quarter for conferences, educational events, and meetings.

Bonus Points

• Experience in medical or health-professions education; nursing or NP program experience is a plus.
• Familiarity with HubSpot or a similar CRM.
• Comfort working with usage data in spreadsheets.

Salary Range

$75,000 - $100,000 annually, plus a sales incentive opportunity and stock options.

Benefits

• Remote First - Make a difference from wherever you want to work.
• Flexible Time Off - No accruals, just real work-life balance.
• 100% Individual Health Coverage - We got you covered!
• Equity - From day one, you’ll have a stake in our future growth.
• 401(k) - We support your financial future with up to 5% matching.
• Team Events - Get to know the team at an annual company retreat and more.
• Annual Work Anniversary Stipend.
• Monthly Wifi & Phone Reimbursement.
• Short Term & Long Term Disability.

Company Description

Sketchy Group LLC is an Equal Opportunity Employer. All applicants will receive consideration without discrimination on the basis of race, religion, color, sex, age, sexual orientation, marital status, national origin, disability or any other basis prohibited by applicable law.