Network/Security Engineer Proxy (Skyhigh SWG)

Our client, an IT Services organization supporting commercial and federal clients, is seeking Network Security Engineer with Skyhigh SWG Proxy experience. This role is 100% remote and can be anywhere in the US. Responsibilities / Scope: - Operate & Engineer - Own SWG policy lifecycle: design - peer review - test - deploy - validate. Keep hierarchy sane; keep lists accurate and minimal. - Maintain TLS inspection posture and exception handling (pinning-safe), with documented rationale and owner for each exception. - Troubleshoot at Scale - Lead packet-through-analytics investigations; produce clear RCAs with captures, logs, and sequence diagrams. - Harden & Improve - Reduce legacy exceptions, remove dead objects, and optimize PAC/WPAD logic. - Keep rollback plans and versioned artifacts for every material change. - Deliverables (acceptance = artifact exists and is technically correct) o Current-State Assessment (-30 days): Inventory of SWG policies, objects/lists, TLS inspection posture, PAC/WPAD flow, and key data paths; gap list with remediation proposals. o Runbooks & Tests (-60-90 days): o Troubleshooting runbooks (auth failures, TLS errors, PAC issues, proxy vs origin error differentiation). o PCRE test suite with regression cases and performance gates. o Change checklist with rollback criteria and canary plan. o Quarterly Hygiene Pack: Exception review (add/remove decisions with owners), object cleanup report, and prioritized improvement backlog. o Incident RCAs: For P1/P2 proxy incidents, RCA within 5 business days with evidence and corrective actions. - Evaluation / Verification o Live Exercise: Given a synthetic outage (e.g., SSO app fails behind TLS inspection), isolate cause using packet capture + logs and propose a safe change with rollback. o PCRE Test: Author a performant pattern for a non-trivial URL/classification case; demonstrate why it won-t backtrack catastrophically. o Policy Review: Walk through a hierarchy change (lists, inheritance, bypass logic) and defend design/rollback-clarity over theatrics. Required Skills - Must be US Citizen due to government clearance requirement - Must be eligible for Public Trust (active DoD Secret is a plus) Mandatory Qualifications - Skyhigh SWG (SkyHigh) - 3+ years administering Skyhigh Secure Web Gateway in production (>10k users). - Expert in policy hierarchy/inheritance, object & list management, staged rollout (test-pilot-prod), logging export, versioning, rollback. - Proxy Engineering - Forward/reverse proxy modes; explicit vs transparent; PAC/WPAD design and distribution. - SSL/TLS inspection: cert chains, pinning impacts, ALPN, HTTP/2 behavior, auth flows (Kerberos/NTLM, SAML/OIDC). - Safe bypass strategies (domain/SNI/IP/risk-based) without degrading coverage. - Layer 3 & Internet Fundamentals - Routing & addressing (CIDR, MTU/fragmentation/PMTUD, NAT44/66, VRFs), basic BGP/OSPF, DNS recursion/forwarding and failure modes. - Ports & Protocols - TCP/UDP behavior, ephemeral ranges, TLS handshake/SNI, and middlebox interactions (no QUIC/HTTP-3 requirement). - PCRE - Writes and reviews complex PCRE (lookarounds, backreferences, atomic groups) with an eye for performance (avoid catastrophic backtracking). - Troubleshooting: Packets + Analytics - tcpdump/Wireshark proficiency (TLS/HTTP analysis, TCP dynamics). - Log correlation at scale (e.g., Splunk/ELK) to isolate issues off-box (client, network, IdP, upstream). - Can distinguish origin responses vs proxy-generated errors and document root cause. - Communication & Prioritization - Clear stakeholder comms; triage correctly under load-doesn-t treat every noisy issue as P1. Apply tot his job

Back to blog

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...