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Job Category:

Customer Service, Technical Support

Pay: $25 an hour

Full Job Description

Who is Smile?:

Smile, a developer of the B2B SaaS productivity tool TextExpander, has been making people more productive for over 15 years. While returning millions of hours of productive time to our customers, we’ve grown from a 2 person team to a team of 30 – all while remaining self-funded and profitable!


We’re looking for a proactive, problem-solver to join us as a part-time contract-based Customer & Technical Support Specialist for weekend support. As our Weekend Customer & Technical Support Specialist, you will assist current and potential customers with everything from general inquiries to educating them on Smile products to resolving technical support issues. All support is via email, there is no phone work!


  • Respond in a timely manner to customer service emails about all Smile products, including the following issues:
  • pre-purchase
  • installation
  • usage / how-to
  • problem-solving workarounds
  • Review and forward refund requests for processing
  • Answer and forward bug reports
  • Answer requests for donations and review software
  • Forward business, marketing, and press inquiries as appropriate
  • Develop a list of top inquiries (for future product improvements)
  • Use & update the set of stock answers


  • Familiarity with macOS
  • Excellent written communication skills
  • Self-motivated, and comfortable with little supervision
  • Moderate and friendly tone with all customers
  • Available at least once every four hours from 8am-10pm US timezones, weekends
  • Apple Mac computer running most recent version of macOS
  • High-speed, reliable Internet connection


  • College education and/or previous customer service experience
  • Expertise with macOS
  • Familiarity with Windows
  • Experience with iPad
  • Experience with iPhone
  • Experience working remotely


  • Contract only
  • Remote only
  • Approximately 4 hours per weekend, somewhat variable
  • Actual work hours flexible
  • Time off negotiable
  • $400 (approx. $25/hour) assuming all duties and high availability
  • Potentially ongoing subject to a monthly review of work quality

Smile develops productivity software for Mac, Windows, Chrome, iPhone, and iPad. Headquartered in San Francisco, California, Smile is a closely-knit, geographically diverse, remote-first company. We have proudly served our customers for over 15 years.

At Smile, we embrace diversity. We strongly encourage underrepresented minorities to apply, even if they’re not sure they meet all qualifications.

Smile provides equal employment opportunities (EEO) to all employees and applicants for employment. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, or disability status.

Company – Smile

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