CNO Training Environment Administrator

Bitwise; Maryland; On-site; USD 267,000 - 314,000; Full time

Benefits offered by this job

Top salaries

PTO flexibility

11 federal holidays

Snow days

401(k) match

Full benefits

Education assistance

Spot bonuses

Job summary

Bitwise is seeking a senior cybersecurity operations professional to oversee the mission-critical training environment, acting as administrator and proctor for practical examinations that support customers’ operational readiness.

You will configure target devices, set up virtual machines, manage exam environments, and collaborate with training coordinators and SMEs to evaluate trainee performance and recommend improvements.

Qualifications

• 12+ years in cybersecurity operations
• Bachelor's degree in a technical discipline (or 4+ additional years of relevant experience in lieu of degree)
• Strong background in Windows exploitation and security
• Proficiency with scripting languages including PowerShell, Bash, and Python
• Hands-on knowledge of VSphere and virtual machine management
• Familiarity with collaboration and learning management platforms including Confluence, Mattermost, and Moodle
• Active TS//SCI clearance with polygraph

Responsibilities

• Oversee our mission-critical training environment as administrator and proctor for practical examinations
• Manage quality control checkpoints, exam environments, and coordinate course rosters
• Schedule exams and collaborate with training coordinators and subject matter experts
• Configure target devices, set up virtual machines, and develop infrastructure for rigorous assessments
• Modernize the platform by adopting new tools and automating repetitive processes

Skills

Cybersecurity operations

CNO tradecraft

Windows exploitation

PowerShell

Bash

Python

VSphere

VM management

Collaboration platforms

Security clearance

Education

Bachelor's degree or equivalent experience

Tools

Confluence

Mattermost

Moodle

Job description

An active TS//SCI clearance with polygraph is required for this role

Hey!

Bitwise is a leading provider of mission-focused intelligence solutions that advance national security for the Intelligence Community and Department of Defense. We're a small and growing company, so you can expect to hop in on the ground floor with us and be a consequential member of the team. You'll be more than a contract performer for us — you'll also be asked for ideas to improve our company and improve your career, and you'll contribute to our team culture. We value growth and community above almost all else, so we gather regularly for game nights, happy hours, tech talks, and plenty more. We think you'll like it here!

Remember, Bitwise is not a cult.

What We Look For

Bitwise hires talented engineers who are driven by purpose and who value a culture of technical excellence, growth, and overall wellness. We deliver new and innovative intelligence solutions to our customers at the very forefront of our country's national security missions. And we do it every single day. Our work matters, and so will you.

We ask that every new hire be able to:

• Contribute meaningful thought leadership — if not right away, over time
• Interact with our customers and earn their confidence in your abilities
• Be detailed, even if that means taking a little more time to get it right
• Contribute their ideas and ideals to improve all aspects of our company
• Allow us to invest in their education so we both grow together
• Know and live our core values every single day

About this Role

You will oversee our mission-critical training environment, serving as both administrator and proctor for practical examinations that directly support our customers' operational readiness. This role sits at the intersection of technical infrastructure management and training program excellence — you'll ensure that every exam environment runs smoothly while continuously improving how we deliver assessments and measure trainee performance.

Your day-to-day will be dynamic and hands-on. You'll manage quality control checkpoints, oversee exam environments, and maintain clear, timely communication with trainees. You'll coordinate course rosters, schedule exams, and work closely with training coordinators and subject matter experts to evaluate trainee performance and recommend improvements. You'll be the architect of testable scenarios — configuring target devices, setting up virtual machines, and developing the infrastructure that makes rigorous practical assessments possible.

Beyond day-to-day operations, you'll have the opportunity to modernize our platform. You'll augment our testing systems with new tools and technologies, develop and maintain scripts to automate repetitive processes, and contribute to the continuous evolution of our course systems. This means you'll get hands-on with infrastructure, scripting, and systems thinking — all while directly supporting the training mission.

Requirements

• 12+ years of experience in cybersecurity operations, with deep familiarity with CNO operational tradecraft and guidance
• Bachelor's degree in a technical discipline (or 4+ additional years of relevant experience in lieu of degree)
• Strong background in Windows exploitation and security
• Proficiency with scripting languages including PowerShell, Bash, and Python
• Hands-on knowledge of VSphere and virtual machine management
• Familiarity with collaboration and learning management platforms including Confluence, Mattermost, and Moodle
• Active TS//SCI clearance with polygraph

Preferred Skills

• Experience with Unix exploitation and security
• Demonstrated expertise in scripting for VSphere and VM management
• CNO operator certification

Benefits at Bitwise

• Top salaries because we're top performers
• Pick your PTO — Everyone values time and money differently, so we give you the flexibility to choose between 3 and 5 weeks of PTO with a corresponding adjustment to your pay. Your choice, your balance.
• All 11 federal holidays, paid!
• Up to 2 snow days, paid!
• We'll quadruple (4x!) the first 6% you contribute to your 401(k), giving you up to a 24% company match. Contributing less than 6%? Unclaimed matches come right back to you as extra income, giving you a guaranteed 24% that goes to your retirement, to your paycheck, or both. C'mon now!
• 100% employer-paid medical, dental, vision, life, and disability insurances. That's a lot. Already covered on health insurance? No problem — we'll trade you this benefit for a boost to your salary instead.
• $5,250 annual education assistance for training, certifications, tuition, and even student loan repayments.
• Spot bonuses for obtained certifications, customer recognition, and just about anything else that makes us go "Hot damn!". We hope to say that many times about you.

Salary Range

$266,500 – $313,500

This range includes our flex income and depends upon your annual work hours.

Salary is determined on an individual basis following the interview process and considering various factors such as years of experience, skills, education, and certifications.

What to Expect After Applying

You'll get an email from us right away to acknowledge your application. After that, we'll:

• Send over additional company materials for you to review
• Schedule a video call to talk about you, our company, and your place in it
• Craft a delightful offer package for you and record a video walkthrough
• Work closely with you through onboarding. We'll keep it joyful and easy.

Disclaimers

Bitwise is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other legally protected status. All employment decisions are based on qualifications, merit, and business needs.

Compensation for this position, including all compensation options, will be determined on an individual basis following the interview process.

If you require accommodations at any stage of the application or interview process, please reach out to us.

Last updated: 8/17/26