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AI Enablement & Community Lead

May 27, 2026

About Coalfire Coalfire is on a mission to make the world a safer place by solving our clients’ hardest cybersecurity challenges. We work at the cutting edge of technology to advise, assess, automate, and ultimately help companies navigate the ever-changing cybersecurity landscape. We are headquartered in Chicago, Illinois with offices across the U.S. and U.K., and we support clients around the world. But that’s not who we are – that’s just what we do. We are thought leaders, consultants, and cybersecurity experts, but above all else, we are a team of passionate problem-solvers who are hungry to learn, grow, and make a difference. Position Summary Coalfire is in the middle of a deliberate, company-wide transformation in how we work — and AI is at the center of it. This role exists to make sure that transformation actually takes hold. As our AI Enablement & Community Lead, you'll own the human side of AI adoption at Coalfire. That means building the learning programs, communities of practice, and internal evangelism efforts that help our people go from AI-curious to AI-capable. You won't just teach tools — you'll shape how Coalfire thinks about and grows with AI over the long term. This is an individual contributor role on the AI & Data team, with high visibility across the organization and direct influence on how thousands of Coalfire employees experience AI in their day-to-day work What You'll Do<div>Learning & Development </div> <ul> <li>Design, build, and continuously improve a curriculum of AI training programs spanning foundational literacy, role-specific fluency, and advanced practitioner development</li> <li>Partner with functional leads across the business to understand skill gaps and tailor learning pathways to specific roles (advisory, delivery, operations, etc.)</li> <li>Develop and manage self-paced resources, workshops, certifications, and onboarding materials that scale across a distributed workforce</li> <li>Track learning outcomes and adoption metrics, using data to continuously sharpen what's working</li> </ul> <div> </div> <div>Community & Culture </div> <ul> <li>Build and run Coalfire's internal AI community — creating spaces (channels, forums, events, office hours) where employees can share what they're building, ask questions, and learn from each other </li> <li>Identify and cultivate internal AI champions and power users across the organization </li> <li>Facilitate knowledge-sharing and peer learning so best practices spread organically, not just top-down</li> </ul> <div> </div> <div>Evangelism & Engagement </div> <ul> <li>Be the voice that keeps AI top-of-mind internally — translating complex or abstract AI developments into relatable, relevant narratives for a general employee audience </li> <li>Develop and distribute internal communications (newsletters, announcements, spotlights) that highlight real AI wins, use cases, and learnings from across the company</li> <li>Represent the AI & Data team at all-hands meetings, internal events, and crossfunctional forums</li> </ul> <div> </div> <div>Strategy & Influence </div> <ul> <li>Serve as a thought partner to the Chief AI & Data Officer on the human dimensions of our AI strategy — readiness, culture, change management </li> <li>Collaborate with HR and People teams on integrating AI competencies into talent development frameworks, performance expectations, and hiring</li> <li>Stay current on enterprise AI trends, tools, and adult learning best practices, bringing relevant insights back to the team </li> </ul> What You'll Bring<ul> <li>7+ years of experience in a combination of learning & development, organizational change, technical training, or community building — ideally in a technology-forward or professional services environment</li> <li>Demonstrated ability to take complex technical topics and make them accessible, engaging, and actionable for non-technical audiences</li> <li>Experience building programs from scratch, not just inheriting and maintaining them</li> <li>Strong written and verbal communication skills — you can write a compelling internal newsletter and facilitate a room of skeptical senior consultants</li> <li>Genuine enthusiasm for AI and its practical applications in the workplace; you don't need to be an engineer, but you need to be deeply curious and credible</li> <li>Comfort working in a high-growth, fast-moving environment where the roadmap is still being written</li> <li>Experience working cross-functionally and influencing without direct authority </li> </ul> Bonus Points<ul> <li>Background in cybersecurity, GRC, or professional services</li> <li>Experience with learning management systems (LMS) and adult instructional design</li> <li>Familiarity with enterprise AI tools (Copilot, Claude, etc.) and how they're being deployed in professional environments </li> </ul> <div>$158,000 - $178,000 a year</div><div>The salary range listed is a reasonable estimate of the compensation range for this role based on national salary averages. The actual salary offer to the successful candidate will be based on job-related education, geographic location, training, licensure and certifications and other factors. You may also be eligible to participate in annual incentive, commission, and/or recognition programs. </div> Why You’ll Want to Join Us At Coalfire, you’ll find the support you need to thrive personally and professionally. In many cases, we provide a flexible work model that empowers you to choose when and where you’ll work most effectively – whether you’re at home or an office. Regardless of location, you’ll experience a company that prioritizes connection and wellbeing and be part of a team where people care about each other and our communities. You’ll have opportunities to join employee resource groups, participate in in-person and virtual events, and more. And you’ll enjoy competitive perks and benefits to support you and your family, like paid parental leave, flexible time off, certification and training reimbursement, digital mental health and wellbeing support membership, and comprehensive insurance options. At Coalfire, equal opportunity and pay equity is integral to the way we do business. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. Coalfire is committed to providing access, equal opportunity, and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. To request reasonable accommodation to participate in the job application or interview process, contact our Human Resources team at <a href="mailto:HumanResourcesMB@coalfire.com" style="font-size: 16px;">HumanResourcesMB@coalfire.com</a>.

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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...

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