IT Helpdesk Engineer (Level 2)

# ABOUT US



I run a growing IT company with a passion for all things tech. We love to help people get the most out of their tech. We specialize in Apple products, but we can provide most IT services aside from hardware repairs. Whether it’s managing IT for businesses, troubleshooting home devices, or offering friendly training one-on-one or in a group setting, we aim to provide flexible, customized solutions for our customers.

With over 20 years in the game, I’ve worn a lot of hats, and now it’s time to grow the team. Business is booming, only limited by staff and tooling. I’m looking for a couple of great people to help us grow. Specifically, we’d like a remote help-desk technician as well as a field-service technician to join the team. This job posting is for the remote technician.

We’re all about doing great work and making sure our customers have an amazing experience. If you’re someone who loves problem-solving, delivering top notch service, and constantly learning new things, we’d love to hear from you. Here’s what you’ll need to succeed and thrive with us:



# MUST-HAVE SKILLS



## Top-Notch Communication
While troubleshooting is key, documenting your work clearly and professionally is just as important as your technical skills:

• Document everything
Whether it’s how a problem was solved, what steps were taken, or when something requires further investigation, clear documentation keeps things organized for the team and helps customers feel confident in our work.

• Build a knowledge base
If you solve a problem that isn’t in our knowledge base, you’ll be expected to write an article for future reference, citing any sources or personal experience which helped you come to the solution.

• Communicate professionally
When closing a case, you’ll provide customers with a written summary of the work performed. This isn’t just a formality – it shows customers we care and that they’re in good hands. It also gives us a chance to showcase our attention to detail and the value they received.



## Technical Ability
You don’t need to know everything — nobody does, and we learn along the way — but you should have a solid foundation in Apple and/or Microsoft troubleshooting.

• macOS, iOS, and basic networking
You should be able to troubleshoot common hardware, software, and connectivity issues with confidence. Familiarity with IMAP issues, printer issues, out-of-storage errors, and tech-support scams would help. Experience with Windows devices, M365, Google Workspace, DNS, or security products would be icing on the cake

• Efficiency
We aim to provide fast, effective solutions, avoiding delays that can appear unprofessional and cause clients problems.



## A Friendly, Patient Demeanor
Let’s face it — tech can be frustrating, and most people aren’t tech experts. They come to us because they’re stuck, confused, or worried about their devices. Your job is to be a calming presence.

• Patience
Sometimes customers won’t know the right terminology or may struggle to explain the issue. You’ll need to guide them gently and respectfully.

• Empathy
Customers should feel heard and supported, even if the issue is trivial, and even if they caused it.



# OPTIONAL SKILLS



These aren’t required, but if you’ve mastered any of these, you’re ahead of the pack! Demonstrating proficiency in these areas will earn you a raise.

## Advanced Troubleshooting
• Deeper knowledge of troubleshooting Apple devices and ecosystems
• Experience with diagnosing more complex network or server-related issues
• Understanding of how to find solutions to problems no one on the Internet has documented before, such as by isolating items in the /Library and ~/Library folders

## Call Handling
• While phone calls aren’t mandatory for this work from home position, many of our customer interactions happen over the phone.
• If you’d like to handle calls, you need to be able to explain technical concepts in Standard American English or another major American dialect, and remain composed when things don’t go smoothly.

## Decision Making
• Assess a situation, make informed decisions on the spot, and know when to escalate a case to someone else.
• Proactively identify potential solutions to customer issues or business problems. As we gain trust in your decision making, you’ll gain the authority to make decisions without approval.

## Scripting (Bash, ZSH, AppleScript, and/or PowerShell)
• As we move more devices to Mobile Device Management (MDM) and Remote Monitoring and Management (RMM) tools, scripting becomes more important.
• We use Addigy as an excellent multi-tenant MDM solution, but if you’ve worked with JAMF or any other Apple MDM platform, your skills will translate easily.



# DAILY RESPONSIBILITIES

• Triage our inbound email and text communication.
• Assist customers with a wide variety of technical issues and questions.
• Thoroughly troubleshoot, researching when needed, to reduce the need for on-site visits.
• Document solutions and contribute to the knowledge base.
• Work independently without needing constant supervision or coaching.



# WHY JOIN US?

Working with us isn’t just about fixing things — it’s about helping people navigate technology with confidence. Here’s what we offer:

## Flexible Work Arrangements
We know life happens. We offer flexibility in working hours and locations.

## Professional Development
We want you to grow with us. If you’re interested in developing new skills (like scripting or advanced troubleshooting), we’ll support your learning and development.

## A Positive Work Environment
We’re a small, growing team that values respect, collaboration and continuous improvement.



# HOW TO APPLY

If this sounds like the kind of environment where you’d thrive, we want to hear from you!

Reply to this job posting with your resume and a brief cover letter explaining why you’re interested in this role.

In your cover letter, be sure to answer the following:

1. Describe a challenging technical issue you’ve solved. How did you figure it out?

2. Share a time where you went above and beyond for a customer.

3. Mention a technical area where you feel confident, as well as one where you’d like to grow.

4. If you have a grammar obsession, you might have noticed a small handful of minor grammar, syntax, or typography errors in this job post. For bonus points, feel free to mention one that you notice!



Join us on this exciting journey — let’s grow together!