Grow in Cybersecurity: TechOps Analyst at Evolve

Evolve Security; Chicago (IL); Hybrid; USD 75,000 - 90,000; Full time

Job summary

Evolve Security in Chicago, IL is seeking a TechOps Analyst who bridges IT operations and offensive security. You will own onboarding and health of client integrations, including Kali testing appliances, cloud access, and scope configuration.

The role covers cloud IAM, scripting, and deployment work with Kali, VMware, and cloud tooling. Security+ is required; 1–2 years experience helps you grow into broader security testing.

Qualifications

• 1–2 years of experience in IT operations, TechOps, or information security.
• Strong Linux administration and Kali Linux troubleshooting.
• Experience with virtualization platforms (VMware, Hyper-V, Proxmox, VirtualBox) and VM images.
• Solid networking fundamentals (TCP/IP, DNS, DHCP, VPN).
• Working knowledge of AWS, Azure, and/or GCP IAM (roles, policies, service principals).
• Scripting experience in Python, Bash, PowerShell.
• Familiarity with Git, Docker, Ansible, Terraform, and CI/CD pipelines.
• Security+ is required; OSCP/PNPT a plus.

Responsibilities

• Deploy, configure Kali Linux testing appliances across VMware, Hyper-V, Proxmox, VirtualBox, and cloud environments.
• Troubleshoot client-side deployment issues (boot, network, DNS, DHCP, firewall, VPN).
• Monitor appliance health and connectivity; assist clients to restore access when offline.
• Guide cloud integration setup for AWS, Azure, and GCP IAM; validate permissions for assessment tools.
• Review and validate client scope, IP ranges, domains, and assets against SOW/ROE.
• Create and maintain runbooks and setup guides for deployment and cloud integrations.
• Automate onboarding/validation tasks using Python, Bash, PowerShell and IaC.
• Act as technical point of contact during kickoff and onboarding.

Skills

Linux admin

Kali Linux

VMware

Networking basics

Cloud IAM

Python

Bash

PowerShell

Git

Docker

Ansible

Terraform

Pentest basics

Security+

Client communication

Tools

ScoutSuite

Prowler

Pacu

Job description

Grow in Cybersecurity: TechOps Analyst at Evolve - Remote

This role is an excellent entry point for professionals looking to bridge IT operations and offensive security. It requires just 1-2 years of experience but demands a broad, hands-on technical skillset - making it a strong accelerator for early-career cybersecurity professionals.

Compensation context: The $75,000-$90,000 range is competitive for a junior-to-mid security analyst in Chicago, slightly above the US national median for Security Analysts (~$70,000-$80,000 at this experience level). It reflects the multi-disciplinary demands of the role (cloud IAM, Linux, networking, scripting).

• Multi-cloud IAM and security tooling (AWS, Azure, GCP) - extremely high market demand
• Offensive security infrastructure and Kali Linux - foundational for a pentest career path
• Client-facing consulting and technical communication

Green flags: Working alongside a dedicated offensive security (OSOC) team exposes you to real penetration testing methodology early. Evolve Academy's #1-ranked bootcamp status signals a learning-first culture. The Security+ requirement with strong encouragement for OSCP/PNPT signals a clear certification progression path.

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Potential red flags: The role is broad - TechOps, client onboarding, cloud, scripting, and partial pentest support - which could mean context-switching and workload pressure. Candidates should clarify team size and ticket volume during interviews. The "other duties as assigned" line warrants follow-up on scope boundaries.

Evolve Security is looking for an OSOC Security Analyst with a TechOps focus to join our growing team. This position sits between our offensive security team and our clients, making sure every engagement starts on solid ground. You will own the technical onboarding and health of client integrations, including Kali testing appliances, cloud access, and scope configuration, and you will troubleshoot client-side issues so our testers can focus on testing. You will also support penetration testing and eASM activities alongside the OSOC team.

Key Responsibilities

• Deploy, configure, and support Kali Linux testing appliances (ISO, OVA, and VM images) in client environments across VMware ESXi, Hyper-V, Proxmox, VirtualBox, and cloud-hosted instances
• Troubleshoot client-side deployment issues such as boot failures, network/VLAN placement, DHCP/static IP configuration, DNS resolution, proxy and firewall restrictions, and outbound connectivity (VPN, reverse SSH, WireGuard/OpenVPN tunnels)
• Monitor the health and connectivity of deployed testing appliances and proactively work with clients to restore access when appliances go offline
• Guide clients through cloud integration setup for AWS (cross-account IAM roles, read-only policies), Azure (app registrations, service principals, role assignments), and GCP (service accounts, IAM bindings), and validate that the granted permissions are sufficient for assessment tooling such as ScoutSuite, Prowler, and Pacu
• Review and validate client scope before and during engagements, confirming that IP ranges, domains, subdomains, web applications, and cloud accounts are entered correctly and match the SOW and Rules of Engagement
• Verify asset ownership (WHOIS, ARIN/RIPE, DNS records, cloud provider attribution) and flag third-party hosted or out-of-scope assets before testing begins
• Maintain and improve internal testing infrastructure, appliance images, and build pipelines, keeping Kali builds patched, hardened, and preloaded with the standard OSOC toolset
• Automate repetitive onboarding and validation tasks (appliance provisioning, connectivity checks, scope validation, cloud permission checks) using Python, Bash, PowerShell, and infrastructure-as-code tools
• Act as the technical point of contact for clients during kick-off calls and onboarding, translating technical requirements into clear, actionable steps for client IT teams
• Escalate integration blockers, scope discrepancies, and security incidents to the appropriate client contacts or internal team members
• Review the eASM dashboard and assist with validating vulnerabilities identified by the ASM system when needed
• Create and maintain documentation, runbooks, and client-facing setup guides for appliance deployment and cloud integrations
• Assist in maturing Evolve Security processes, procedures, templates, and methodologies to improve onboarding speed and engagement quality
• Take on other duties as assigned to support the growth and expansion of enterprise and academy initiatives

Requirements

• Passionate about cybersecurity and infrastructure, with a curiosity to learn
• 1-2 years of experience in IT operations, system administration, TechOps, or information security
• Strong Linux administration skills, with hands-on experience using and troubleshooting Kali Linux
• Experience with virtualization platforms (VMware, Hyper-V, Proxmox, VirtualBox) and building or customizing VM images and ISOs
• Solid networking fundamentals: TCP/IP, subnetting, routing, VLANs, DNS, DHCP, NAT, firewalls, and VPN technologies
• Working knowledge of AWS, Azure, and/or GCP identity and access management (IAM roles, policies, service principals, service accounts)
• Scripting experience in one or more of: Python, Bash, PowerShell
• Familiarity with TechOps tooling such as Git, Docker, Ansible, Terraform, or CI/CD pipelines
• Foundational understanding of penetration testing methodology and common offensive tools
• Familiarity with cloud security tooling (ScoutSuite, Prowler, Pacu, ROADtools) is a plus
• Security+ required; Linux, cloud, or offensive certifications a strong plus (Linux+, RHCSA, AWS Solutions Architect / SysOps, AZ-104, AZ-500, PNPT, OSCP, or equivalent)
• Strong troubleshooting mindset and the patience to work through problems with non-technical or busy client IT teams
• Ability to interface with clients, using clear communication and consulting skills
• Strongly self-motivated, organized, and able to manage multiple client onboardings at once
• Strong communication skills (oral and written) and ability to work as part of a team

About Evolve Security

Evolve Security is a cybersecurity services firm headquartered in Chicago, IL. We are dedicated to improving our clients' security posture by providing continuous penetration testing, training services, and talent solutions.

In addition to our professional cybersecurity service offerings, Evolve Security offers a cybersecurity bootcamp, "Evolve Academy", currently ranked the #1 cybersecurity bootcamp in the world. The Cybersecurity Bootcamp in Chicago provides immersive training, giving students the concrete and practical skills needed on the job. Students gain real work experience through live security assessment work that they perform on not-for-profit companies.

We are passionate about directly improving our customers' security posture, and we proudly train others to help meet the need for qualified cybersecurity talent.

Is this OSOC Security Analyst role fully remote or office-based? The job posting does not explicitly state remote or on-site status. The role is based at Evolve Security's Chicago, IL headquarters, so candidates should confirm the work arrangement during the interview process. What certifications are required or preferred for this position? Security+ is required. Preferred certifications include Linux+, RHCSA, AWS Solutions Architect/SysOps, AZ-104, AZ-500, PNPT, OSCP, or equivalent cloud and offensive security credentials. What is the salary range for this role? The posted salary range is $75,000-$90,000 per year, depending on experience and qualifications. What experience level is required for this position? The role requires 1-2 years of experience in IT operations, system administration, TechOps, or information security, along with hands-on Linux and networking skills. What cloud platforms will I work with in this role? You will work with AWS, Azure, and GCP, specifically around IAM configuration - including cross-account roles, service principals, and service accounts - to support security assessment tooling like ScoutSuite, Prowler, and Pacu.

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