Security Awareness Training Designer at Anagramsecurity

About Anagram Anagram builds lasting awareness by teaching people to see, think, and act differently in an always-changing security landscape. Instead of boring videos and pointless quizzes, we have puzzles, simulations, and an AI companion that coaches people in real time. We do more than check boxes. We change behavior by making ongoing security second nature. Fortune 500 companies like Disney, Kraft, and Pfizer use us because their employees actually absorb our training. We're looking for a Security Awareness Content Designer to own our training modules end-to-end — researching what's happening in the threat landscape, writing scripts, coordinating video production, creating puzzle content, and QAing everything before it ships. This is a part-time contract role working closely with our Product Manager, with real ownership and flexibility to work independently. We're looking for someone who lives in the threat landscape and can turn it into content people actually engage with: • You understand the threat landscape and pitch topics that matter. You closely follow the human side of cybersecurity, spot what's emerging, and regularly bring topic proposals to the team with a clear case for why they matter. • You own the module lifecycle end-to-end. Once a topic is greenlit, you write the script, manage production with our video contractor, select the puzzle, write the content, and see it through to ship. • You develop puzzle content that makes people think. You help design new puzzle concepts for our engineering team to build, thinking through mechanics, UX, and learning outcomes. You keep ADA compliance in mind throughout. • You create custom modules for enterprise customers. When customers need tailored content, you write custom scripts and puzzles based on the materials they provide and deliver them on time. • You care about quality. Before anything ships, you review the full module, video and puzzle together, and flag anything confusing, inconsistent, or off. • You're self-managed and reliable. You set your own pace, keep your workload organized, and consistently hit your deadlines and deliverables without needing someone to follow up. • You communicate clearly. You keep the team informed, surface issues early, and can work across time zones and schedules without things falling through the cracks. • Nice to have: experience with multi-language content or managing translation workflows. Even better if your cybersecurity expertise extends into the developer security space. This role is a great fit if you're energized by autonomy and breadth. It's probably not the right fit if you prefer: • A defined content calendar handed to you. Most of your topic ideas will come from your own research and instincts. • A lot of creative direction upfront. You'll get context and feedback, but you're expected to bring a strong point of view. • A narrow focus. You'll move between research, scripting, production coordination, QA, and customer work regularly. • A lot of structure. You set your own pace, hit your deadlines, and flag issues before they become problems. Working at Anagram We're a fully remote startup that values deep work and flexible collaboration. Values Move fast, adapt: Jump in, make decisions, break things, fix them, and learn. If something doesn’t work, toss it and move on. Progress over perfection — we're always growing. Ego-free zone: No jerks, no drama. Every voice on the team matters. We deliver results, embrace failures, celebrate wins, and make magic happen together. Own it: See a problem? Fix it. Idea? Pitch it. Question? Ask it. Everyone has the power and responsibility to make us better. This isn’t a place for passengers. How We Work No timesheets: Results matter, schedules don't. Work when it's right for you. Real-time feedback: Immediate, clear, and constructive. Growth shouldn't wait. With kindness: Respect others, communicate with care, assume good intent. Fully remote: Work where you work best. Twice a year, we meet in person. Benefits Flexible PTO: Take time when you need it, federal holidays and Dec 24–Jan 1. Optional Fridays: No internal meetings. Work or recharge as needed. Healthcare: Medical, dental, and vision provided. Parental leave: Time off for life’s biggest moments. Equity: Own a piece of what we’re building. 401(k) matching: Save for the future with company matching. Stipends: Office setup, remote work, and learning support. We are an equal opportunity employer. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or genetic information. We provide reasonable accommodations for individuals with disabilities.