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Technical Support Specialist Tier 2 (Remote)

June 13, 2026

The following states/districts are excluded from this job ad AK, CA, CO, CT, DC, HI, LA, MA, MN, MO, NE, NV, NH, NJ, NM, NY, ND, OR, PR, RI, VT, WA, WY Location Remote in any United States jurisdiction not excluded from this job advertisement. We're looking for a Technical Support Specialist Tier 2 to solve technical issues, diagnose complex software and system problems, and ensure timely resolution of incidents! Apply today to join a mission-driven team supporting critical healthcare technology environments within the Department of Veterans Affairs (VA). Position Description The Technical Support Specialist Tier 2 handles escalated technical issues that cannot be resolved by Tier 1 Help Desk Support. The Technical Support Specialist Tier 2 will diagnose complex software and system problems in cloud environments, work directly with customers and internal teams, and ensure timely resolution of incidents. Minimum/General Experience 3 years of information technology experience Minimum Education High School Diploma Essential Skills/Qualifications Strong understanding of web-based software products, systems, and cloud platforms (e.g., Azure, AWS) Strong proficiency in troubleshooting tools, logs, and diagnostic methods Strong experience with operating systems (e.g., Windows, Linux) Strong experience with ticketing systems (e.g., ServiceNow (SNOW), Jira) Familiarity with networking fundamentals (e.g., Domain Name System (DNS), Dynamic Host Configuration Protocol (DHCP), Transmission Control Protocol/Internet Protocol (TCP/IP), Virtual Private Network (VPN), firewalls) Ability to read and interpret system logs or error reports Excellent written and verbal communication skills Strong problem solving and analytical thinking skills Ability to work independently on complex issues Experience with scripting or automation (e.g., PowerShell, Bash, Python) (preferred) Experience with Infrastructure as a Service (IaaS), cloud platforms, or enterprise IT environments (preferred) Experience with Tier 2 or advanced support, technical troubleshooting, clinical and patient data workflows, and regulatory awareness (preferred) Knowledge of VA operations (e.g., VistA, Telehealth and Scheduling) (preferred) Knowledge of Electronic Health Record (EHR)/Electronic Medical Record (EMR) systems (preferred) General Physical Requirements needed to perform the essential functions of this job may vary based on the location of the assignment. Assignment Location - Remote Sedentary Work - Exerting up to 10 pounds of force occasionally and/or a negligible amount of force frequently or constantly to lift, carry, push, pull or otherwise move objects. Typing, communicating, repetitive motions. Close visual acuity to prepare and analyze data, view computer monitors and read. May need to view presentation screens and other visual aids in a virtual setting. Inside environmental conditions with protection from outside elements. Security Ability to obtain/maintain a Federal Civilian Public Trust U.S. Citizenship or Permanent Resident that has lived in the United States for at least 3 years Federal Civilian Public Trust Consists of a review of up to but not limited to Covers 10 year period and in some instances lifetime events OPM Security Investigations Index (SII) DOD Defense Central Investigations Index (DCII) National Agency Check (NAC) records FBI name check FBI fingerprint check Credit report check Written inquiries to previous employers and references listed on the application for employment Potential interviews with the subject, spouse, neighbors, supervisor, coworkers Law enforcement check Court records check Education check- Attendance and Degrees Acceptable Credentials Tasks/activities include, but are not limited to Investigates and resolves technical issues escalated from Tier 1 support Performs advanced troubleshooting across software, hardware, cloud networks, and/or C# applications Documents issues, solutions, and root causes in the ticketing system Collaborates with engineering, Tier 3 Support, and/or development teams on unresolved or systemic issues Provides guidance and mentorship to Tier 1 Support agents Identifies recurring problems and recommends process or product improvements Assists with system updates, patches, and configuration changes Communicates clearly with customers regarding progress and resolution Follows Service Level Agreements (SLAs) and ensures timely ticket handling Participates in on-call activities when required Compensation & Benefits The annual projected pay range for this position is $45,000.00 - $50,000.00 with consideration being given to various factors including but not limited to qualifications, experience, job responsibilities, and geographic location. Oxley Enterprises, Inc. offers a full array of benefits including Medical, dental, vision and prescription drug coverage for you and your family. Life Insurance, short-term disability and long-term disability paid for by the Company. Supplemental coverages including Accident, Critical Illness, and Hospital. Additional Life insurance coverage for you and your dependents. 401k plan with various options to select based on your retirement goals. Oxley Enterprises®, Inc. is a certified service-disabled veteran-owned (SDVOSB), veteran-owned (VOSB), and woman-owned small business (WOSB) that has 26 years of experience building and delivering quality IT systems and programs. Oxley is ranked in the INC 5000 7 times (2016, 2017, 2018, 2021, 2023, 2024, 2025). Oxley is a 2019 - 2025 Department of Labor HIRE Vets Medallion Award Winner. Oxley is Virginia Values Veterans certified. All qualified applicants will receive consideration for employment without regard to any status protected by applicable federal, state, or local law. If you require a reasonable accommodation to apply for a position at Oxley Enterprises, Inc., please send an email to our Human Resources Department at careers@oxleyenterprises.com with the following information Subject Line Accommodation Request Provide a description of your accommodation request Include your contact information Full name, Email address, Best number to reach you (optional) We participate in the E-Verify program. http// Apply To This Job

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...