Customer Success Specialist
- Pay
- $75,000 – $100,000 per year
- Location
- Remote (US)
- Job type
- Full-time
- Level
- Mid-level
- Experience
- 1+ year
- Education
- Bachelor's degree
- Listed
- 21 days ago
Skills & highlights for this role
- customer success
- onboarding and training
- CRM
Also useful
- HubSpot
- usage data analysis
- medical education
Stated benefits & perks
- Health
- 401k match
- Flexible pto
Position Summary
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.
What We’re Looking For
- 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.
Additional information
If you don’t have 100% of the bullets listed above, that’s okay! We know there are no perfect applicants. If you are passionate about making a meaningful difference, we want to hear from you! Learn more about Sketchy’s culture at sketchy.com/careers.
Pay and benefits
Salary Range $75,000 - $100,000 annually, plus a sales incentive opportunity and stock options
Our Perks
- 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
Our Company
At Sketchy, we’re transforming how students learn by turning complex topics into unforgettable visual journeys. Our mission? To help students master challenging material, achieve higher scores, and bring their knowledge to life through interactive cases. Through a combination of art, science, and cutting-edge technology, we enable students to learn, retain, and practice—effortlessly. The short version? We’re here to make better clinicians.
All are welcome! At Sketchy, we know a diverse and inclusive team not only makes our product better but our workplace better. Making Sketchy warmer and more inviting for everyone is at the core of our company's culture
Equal opportunity and legal notices
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.
From Sketchy's careers page, first listed on Rolev.ai on October 20, 2026. Rolev.ai is not the employer.
How Rolev.ai helps with this application
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Common questions
What is the salary for the Customer Success Specialist role at Sketchy?
The Customer Success Specialist posting at Sketchy states compensation of $75,000 – $100,000 per year. It is listed as a full-time position. Final pay may depend on location, experience, and interview evaluation on Sketchy's official career site.
Where is the Customer Success Specialist job at Sketchy located?
Yes, this Customer Success Specialist opening at Sketchy is listed as Remote (US). Always check Sketchy's application page for specific state eligibility or relocation policies.
What qualifications are required for Customer Success Specialist at Sketchy?
For the Customer Success Specialist role, Sketchy highlights 1+ year of relevant experience; a bachelor's degree; experience with customer success, onboarding and training, CRM. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.
How do I apply for the Customer Success Specialist position at Sketchy?
This listing links directly to Sketchy's Rippling application page. You can apply directly on Sketchy's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Rippling application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.