Join Our Team

We are a closely knit, geographically diverse company, with roots in the Mac community

Join Our Team

Smile, PDFpen and TextExpander

Smile develops productivity software for Mac, Windows, Chrome, iPad and iPhone. Our award-winning products redefine productivity so that you can get to the finish line sooner, leaving you more time for what comes next.

Who We Are

Read about how we grew from 2 developers with lots of ideas into the team we are today over on our blog.

We love our customers.
We provide fast, friendly, outstanding support.
We treat one another and our customers with respect.
We work together, independently.
We care deeply about what we do.
We attend to details.
We constantly strive to do better.
We create. We solve. We ship.

We are smart, organized, reliable, honest, positive, and personable, and that’s how we’ve managed to successfully ship products for over 15 years as a remote team.


Our customers are why we’re here. They are awesome, productivity-minded individuals like ourselves. Next, we care for each other, our team, whom we work with each day. We’ve been working on providing more and better benefits to live that value.

We are proud to currently offer employees:

  • The flexible schedule which comes with a remote position
  • Healthcare reimbursement plan (ICHRA plan)
  • Paid vacation and sick leave
  • 401(k) plan
  • Profit sharing plan


At Smile we embrace and encourage diversity in our workforce. We strongly encourage all applications, even if you’re not sure you meet all the qualifications.

If you know of someone from an underrepresented community who would be a good fit, please share our job postings with them.

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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