Sales Development Representative – SaaS, B2B

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About Us

At Smile we work on the leading edge of SaaS software for team productivity, TextExpander.  We’re passionate about helping our customers communicate consistently and efficiently at work. 

TextExpander enables you to insert text snippets in any application from a library of content created by you and your team. Just as we strive to communicate clearly, honestly, and effectively, we help teams do the same with TextExpander. We are customers of our own products and use them every day to run our company.

We are a diverse, mostly remote team, working from around the world, headquartered in San Francisco, California. We work both independently and together to solve problems, learn, improve, and most of all, make our customers happy.

Join our remote team, working in a fluid environment as we continually learn and grow.


Smile, developer of the B2B SaaS productivity tool TextExpander, seeks a Sales Development Representative. 

You will help the company meet and exceed revenue goals by generating and qualifying a high volume of outbound B2B opportunities. Assist the sales team by: building out targeted prospecting lists; running a high volume of cold calls and outreach; making connections with decision-makers at companies that fit our customer profile; generating new business opportunities for followup by the sales team. This role is a great opportunity for someone looking to learn and grow into a career in SaaS sales, as there will be a strong opportunity for career growth as we scale our B2B sales efforts.


  • Work with the sales team to develop targeted lists of prospect companies and individuals
  • Run a high volume of outreach to your targets across all channels, with the goal of scheduling introductory discovery calls
  • Make detailed preparation notes for each discovery call generated and strategize with the sales team on each new target
  • Attain and exceed monthly quotas for qualified opportunities generated
  • Log all activity in our Close CRM, maintaining clean and detailed data
  • Collaborate with the sales, marketing, and product teams to share learnings from the field and help define the most effective processes and strategy for the sales team to achieve our ambitious targets


  • 2+ years sales or related business experience
  • Strong desire to develop a career in SaaS sales
  • Self-starter with a strong drive
  • Superb organization skills and attention to detail
  • Strong English writing, voice communication & video conferencing skills
  • Coachable and eager to learn and improve based on constructive feedback
  • Driven, high energy team player
  • Excellent networking and relationship building skills
  • Flexible – we are a developing team iterating on our process and strategy, your feedback, creativity, and adaptability is essential
  • Experience with Mac, Windows, Chrome OS, iOS, CRM, Cloud-based tools

Skills needed to work 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!)

Tech needed to work remotely in this role:

  • High-speed, reliable Internet connection


  • Previous SaaS B2B Sales Development experience
  • Undergraduate degree
  • Experience working with a CRM
  • Experience with remote work


  • High level of autonomy in your role
  • Motivated and creative teammates
  • Flexible schedule
  • Work from our Lincoln, NE office, or work remotely
  • 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 and encourage diversity in our workforce. We strongly encourage all applications, even if you’re not sure you meet all the 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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