Make $100k/year and get training provided with these high paying work from home jobs!

Customer Support Engineer at

Location: Work From Your Home on a Remote-First Team at a Hybrid Remote Company

World Class Pay and Benefits

Starting Salary for a Customer Support Engineer at is $100,000 per year. We offer raises and equity as you grow in the organization.

In-House Training: You have the technical skillset of level 2 or level 3 Tech Support Engineer already. We will take your finely honed technical support skills and provide you with a combination of different training methods that will bring you up to speed on our process, tools, and tech. 

Amazing Team and Peer Support: Our Customer Support team is one of the most tight-knit groups at the company. Everyone enjoys working together on Zoom every day.

Big Company Benefits: You'll get full 🏥 Health/Dental/Vision Insurance coverage (plus 75% of Spouse/Family coverage too), 💰 401(k) with generous matching, 🎄 11 Company Holidays per year, and 🏖 20 PTO/Vacation days.

Brand New Laptop and $1,000: Upon signing, we'll send you a brand new 💻 Apple laptop as well as $1,000 to outfit the rest of your home office with things like a monitor, webcam, keyboard, and mouse.

100% Remote Opportunity

The Customer Support team is 100% remote. However, we travel for regular in-person meetings with the team and the entire company to meet and work together face to face. These meetings are in cities around the US, including Scottsdale, Austin, Orlando, New Orleans, San Diego, Las Vegas, and New York City.

In-person events combine work and fun and are designed to make up for the in-person interaction that occurs in an office job.

We are very excited that COVID-19 restrictions have been lifted and we have fully resumed company travel. 🎉

About is an enterprise secure file transfer & automation app with over 6,000 paying business customers, including Target, Canonical, UPS, Leica, DirecTV, GoPro, Marriott, and more. was bootstrapped by our founder and has been profitable since its founding in 2010. We recently raised $46.5 million of growth equity from Silicon Valley-based Riverwood Capital to accelerate our growth.

In this role, you will be:

  • Responding to customer-initiated interactions such as phone calls and emails (one-on-one communication).
  • Identifying software bugs and feature requests, and coordinating with the relevant team for handling.
  • Providing after-hours emergency support assistance to customers on a rotating basis with other customer support team members.
  • Taking a high-touch approach to support, encouraging frequent interaction with customers and working with them to a full resolution of any issues.

About You:

  • You have excellent written and verbal communication skills, and have real world experience deploying those skills.
  • You bring a top-notch customer demeanor, including patience, understanding, and empathy.
  • You can learn a process and then add to that process. For example, you can learn to use our knowledge base and playbook articles, and then contribute to make them better.
  • You are known for being smart and getting things done. When you take on a project, your team knows you will handle it effectively and efficiently.
  • You have a general understanding of a SaaS environment, including some experience (not necessarily expertise) with several of the following technologies: web applications, networking, internet communication protocols, APIs and/or programming languages, file integration tools and platforms (e.g., AWS, SharePoint, Zapier), and single sign-on tools (e.g., LDAP, Azure AD, Okta)


Insurance Agent at Trailstone Insurance Group

If you join our team, you will…

  • Make passive income – You will get paid on the clients you sold months and years before when your clients renew their policies. Every year you sell, you grow your income from the prior year while working less.
  • Help clients protect their families for the best rate – As an independent agency, we represent more than 40 insurance companies. You’ll run quotes from many carriers in order to ensure that your client finds the right coverage for the right price.
  • Work from great leads – Trailstone Insurance Group is a Dave Ramsey Endorsed Provider. Dave Ramsey and his team connect us with great clients looking for better coverage and a good price.
  • Control your own schedule – You will have complete schedule flexibility and the ability to work completely remote, so you can enjoy your family or the great outdoors and sell on your schedule.

The ideal candidate would…

  • Embrace our philosophy of ”Treating others they way you would want to be treated”
  • Be a Dave Ramsey fan. As mentioned above, we are a Ramsey Endorsed Provider and receive hundreds of referrals from Dave each month.
  • Be looking for an independent contractor relationship with Trailstone Insurance Group where you will grow to a six figure income. So, no salary but we will help you build an income fast.
  • Be looking for a commission schedule more competitive than any other insurance agency.
  • Be an early adopter of technology or willing to learn
  • Be self-driven and not need to a have a “boss” to be successful.


  • Property and casualty insurance licenses – An insurance license can usually be attained within 30 days.
  • Working knowledge of computer software – Microsoft Office products, DropBox, Customer Management Software
  • Great communication skills – written, verbal and listening
  • Be self-motivated – we are looking for a self starter
  • Willingness to be coached and follow a proven process

Other Benefits

  • No prior experience required, although sales experience is welcomed
  • Bonus and incentives
  • Casual business attire
  • Laid back office environment or option to work remotely
  • If you are driven, we can train you and you will succeed and be making six figures within a few years!


Leave a Reply

Your email address will not be published.