Two Chicks With A Side Hustle

Employer: Fleetio


Fleetio is a modern software platform that helps thousands of organizations around the world manage their fleet operations. Transportation technology is a hot market and we’re leading the charge, with raving fans and new customers signing up every day.

As a Customer Support Specialist for Fleetio, your job is to work directly with our customers to support their success using our software. You’ll be directly contributing to our customers’ productivity, satisfaction, and loyalty by providing the highest level of customer service. This is a demanding but rewarding role that requires superior communication skills, a great attitude, and the desire to learn continually.

As a member of the Customer Support team, you’ll work with other highly motivated Customer Support Specialists to manage user interactions via email, phone, and chat. You will work with several other Fleetio teams (Accounting, Engineering, Sales, Customer Success), including providing direct customer feedback to the Product Strategy Team.

Our ideal candidate is someone who is excited to jump in, research, troubleshoot, and would enjoy crushing a queue each day. This person will juggle the phone, online chat, and email support. This is a queue-heavy, frontline support role with 1-2 projects for downtime. This person must be able to work Monday – Friday from 10am-7pm CT.

We’re looking for a personable, high-energy, team-oriented, and tech-savvy team member who excels at helping customers solve their problems. Please take the chance to brag on yourself in your cover letter by including any Support related metrics (CSAT, ticket/case volumes, etc). Be sure to mention coffee in your application so we know you actually read this.

What you’ll be doing

  • Handle inbound customer requests via email, phone, and chat
  • Quickly follow-up to resolve customer inquiries with helpful, personalized responses
  • Identify, reproduce and document issues for the product teams
  • Assist the product teams by testing new features and issue resolutions
  • Spot trends in customer issues and communicate with product teams
  • Work with 3rd party partners to escalate and resolve integration issues
  • Monitor and report on support metrics and KPIs and suggest improvements

What’s in it for you

  • Work with fascinating customers and prospects from all around the world
  • Be a part of an incredible team of “A” players who go above and beyond to make Fleetio a successful company
  • Work remotely from anywhere in the US with a solid internet connection
  • Strong Remote culture focused on cross-team collaboration and company-wide engagement #LI-REMOTE


  • Must reside in the United States
  • Must be able to work Monday through Friday from 10am-7pm CT
  • Ideally, our top candidate has previous experience in Salesforce Service Cloud Omni-Channel
  • Genuine empathy for customers, and desire to make them feel happy and understood
  • Passion for exceptional customer service and appreciation for its role in a company’s success
  • Excellent writing and communication skills
  • Resourceful and determined, yet not afraid to ask for help
  • Natural troubleshooting skills and ability to creatively problem-solve
  • Serious attention to detail and follow-through
  • Ownership of escalation and problem resolution
  • Ability to work in a team environment
  • Excited by technology and its ability to make you more productive


  • 100% health/dental coverage (50% coverage for family)
  • Vision insurance
  • Incentive stock options
  • 401(k) match of 4%
  • PTO – 4 weeks
  • 8 company holidays + 2 floating holidays
  • Parental and bonding leave
  • Dependent care and medical FSA
  • Short and long term disability
  • Community service funds
  • Professional development funds
  • Health and wellness initiatives
  • Mac laptop
  • Monthly catered lunches
  • Fully stocked kitchen with tons of drinks & snacks
  • Remote working friendly since 2012