Smile: Technical Support Lead

Headquarters: San Francisco, CA


Smile, 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 more than 30 – all while remaining self-funded and profitable! We’re now looking to grow the team with the skills of a Support Team Lead to carry on Smile’s track record of exceptional support and customer service.

Work with our talented, internationally diverse, remote team as we learn, grow, and continually improve.

What we’re looking for:
Smile is seeking a technically adept, hands-on Technical Support Lead to lead a team of Technical Support Specialists to provide world-class support to our TextExpander and PDFpen users. Your day-to-day work will include working cross-functionally with engineering and sales to solve complex tier 2 technical problems, mentoring your team, and creating processes that set our team, and our customers, up for success.

Who you are:
You love to troubleshoot and solve problems. You won’t stop until you’ve figured out a solution for our customer.

You have patience and you can read between the lines to understand customers who may not know the technical terms to explain their problems.

You’re driven to help customers and “Passion for Customer” isn’t just one of our values, it’s one of yours too!

Leading and mentoring a team comes second nature.

What you’ll be doing:
Team Lead:
  • Manage the day-to-day activities of the Customer Support team, including monitoring and mentoring employees
  • Monitor the support team’s performance including KPIs and customer feedback so that all interactions align with Smile’s values and history of excellent customer service
  • Provide feedback and guidance to support team by way of performance reviews, one on ones, and other meetings as needed
  • Create repeatable and predictable processes in alignment with Customer Support department objectives and goals
  • Serve as the point of contact between Support, Sales, Engineering, Product, and Marketing teams
  • Continually work to optimize the Support team’s performance, accuracy, and efficiency
  • Coordinate with Sales team for technical support when needed
  • Assist with the Knowledge Base and other supporting and educational materials to ensure that public-facing information is created and edited when necessary
  • Train new team members in Support
  • Recruit, hire and train new team members
  • Work with Product, Marketing, and Launch Day teams to make product updates and releases smooth
  • Track leading customer issues and recommend product changes that optimize & reduce overall support cases and costs

Tier 2 Support:
  • Gain an expert understanding of our SaaS applications, TextExpander and PDFpen, to resolve complex client requests. As a leader in the Customer Support department, you will be expected to stay up to date with application enhancements and understand how to translate enhancements into customer value
  • Work closely with our Product department to understand our development lifecycle as it pertains to the Customer Support department. Act as a customer advocate for client product features and defects
  • Respond to escalated customer service emails, including the following issues:
    • problem-solving workarounds
    • bug reproduction, clarification, and capture
    • crash log capture
    • defect investigations
    • technical how-tos (comfortable working with JavaScript)
    • file bug reports and feature requests in JIRA
    • help manage JIRA (organize, resolve duplicates, highlight high priority issues, etc)
    • update Tier 2 snippets for the Support team

Other duties include
  • Assist with hiring and onboarding process (interviewing, grading projects, etc)
  • Assist with advanced webinars and other customer education projects

  • At least 1-year previous experience in leading a technical customer support team
  • At least 2 years previous experience in a technical customer support role
  • Demonstrated experience working with JavaScript
  • Strong organizational and prioritization skills
  • Strong written and verbal communication skills
  • Demonstrated expertise working with macOS, iOS, Windows
  • Self-motivated, and comfortable with little supervision

Tech needed for the job:
  • High-speed, reliable Internet connection

Skills needed to succeed at Smile

  • Ability to work independently as well as in a team environment
  • Self-motivated, and comfortable with little supervision
  • Excellent written communication skills
  • Comfortable working with a remote team
  • Highly detail-oriented
  • Adaptable, able to learn and grow
  • Reliable, smart, honest, organized, positive, personable (like us!)

  • Experience with remote work
  • College education
  • Familiarity with Smile products
  • Experience with Jira

  • Experience creating knowledge base tutorials
  • Demonstrated experience working with ShellScript
  • Demonstrated experience working with AppleScript

  • High level of autonomy in your role
  • Motivated and creative teammates
  • Flexible schedule
  • Remote Work
  • 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

Smile develops productivity software for Mac, Windows, Chrome, iPhone, and iPad. Headquartered in San Francisco, California, Smile is a closely-knit, geographically diverse company, with roots in the Mac community. We have proudly served our customers for over a decade.

At Smile, we embrace diversity and recognize that we have work to do in that area. 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.

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