Customer Support Representative at Smile

Remote | Entry-level

Customer Support Representative

We at Smile are on a quest to help people work smarter, not harder, and to do that we’re searching for a passionate Customer Support Representative to help assist our TextExpander and PDFpen users with their general inquiries.

If you’re:

  • A natural, technical problem solver
  • A master communicator via email and chat (but won’t shy away from a call)
  • Always learning, innovating, and growing

We want to talk to you!

The general:

The bulk of this position revolves around assisting current and potential Smile customers with everything from general inquiries, educating them on Smile products, and resolving Tier 1 issues.

The specifics:

Support: You’re a pro at managing a support queue. You handle incoming support emails quickly and you escalate tickets that need further investigation to Tier 2. You notice trends within your support cases and raise them to the appropriate teams when necessary. You love keeping the knowledge base up to date and making sure users have the information they need to be successful with Smile’s products.

You have experience:

  • Managing a support queue and answering customer inquiries primarily via email
  • Teaching “how-to’s” over email while making users feel confident
  • Searching and filing bug reports in Jira
  • Acting as a customer advocate for client product features and bugs
  • Meeting and exceeding KPI’s for response times and customer satisfaction
  • Keeping a knowledge base up to date and working on support-specific projects when the queue is maintained

Needed for the job:

  • High-speed, reliable Internet connection
  • 1+ years in technical support of a SaaS product, preferably via email or chat
  • Experience working with macOS, iOS, Windows
  • A great attitude and an eagerness to learn and solve problems

Preferred for the job:

  • College education
  • 2+ years working remotely
  • Strong interest in productivity / working smarter
  • Passion for your work and self-motivation

Why you should join the Smile team:

We’re an established company that’s been around for more than 15 years and have grown from a 2 person team to a team of over 30 – all while remaining self-funded and profitable!

We’re here for our customers, but we’re also here for each other. We are a close-knit, geographically diverse team that lives and breathes our company culture of accountability, integrity, teamwork, and passion for our customers.

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


  • High level of autonomy in your role
  • Motivated and creative teammates
  • Flexible schedule
  • Employment benefits:
    • Healthcare reimbursement plan (ICHRA plan)
    • Paid vacation and sick leave
    • 401(k) plan
    • Profit-sharing plan
  • Contract work also negotiable
  • Salary based on experience

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