Head of Adversary Simulation - North America

Attackers don’t play by the rules. Neither do we. 

Traditional penetration testing is broken—limited scopes, periodic checklists, predictable playbooks. CovertSwarm focuses exclusively on offensive security, delivering constant, unlimited-scope, whole brand attacks via subscription. Our ethical hacking teams (“Hives”) swarm around targets relentlessly, always searching for a new way to compromise them. We aim to breach our clients before real adversaries can, every single day. 

Our North American operation is experiencing 300% year-on-year growth, and we are just getting started. We are looking for a Head of Adversary Simulation – North America to lead this revolution and take our offensive operations to the next level. If you are an ambitious Red Team leader itching to change the industry, this is your call to arms. 

Your mission: Lead a red team revolution 

This is a leadership role with a rebellious twist. As Head of Adversary Simulation for the North American region, you are not just managing a team – you are leading a movement to disrupt the traditional offensive security industry. Your mission is to scale our Americas Red Team from hyper-growth to industry domination. You will own everything from strategy to execution in the region: deciding how we attack next, how to grow and structure the team, and how we continue to wow our clients with never-before-seen attack tactics. In short, you will make sure we swarm, defeat, repeat on a continent-wide scale – redefining what “penetration testing” and “red teaming” means in the process. 

What you will do 

• Scale an elite team– Build and inspire an ever-growing Hive of world-class ethical hackers. Recruit top talent, mentor them into leaders and expand our U.S. Red Team from a fast-growing squad to an unrivalled force. 

• Own the attack strategy – Define and execute the offensive playbook for the Americas. From digital intrusion to physical social engineering, you will decide where and how we strike next to keep clients perpetually on their guard (and safe). 

• Drive relentless delivery – Oversee end-to-end red team operations across the region. Ensure our unlimited-scope attacks stay agile, unpredictable and brutally effective. Every engagement should push the envelope of what is possible in offensive security. 

• Innovate and experiment – Champion a culture of innovation and hacking research. Encourage the team to find new vulnerabilities, develop novel exploits and think like attackers who break the rules (because we do). You will keep us ahead of the curve at all times. 

• Engage and influence – Be the offensive security evangelist for our U.S. clients. Interface directly with customers’ C-suites and boards, translating our hackers’ findings into business insights they can act on. Support our Sales team in big deals with your credibility and vision, and turn prospects into believers. 

• Mentor the Hive – Develop the next generation of adversarial experts. Coach and train your team members in advanced tradecraft, refine their soft skills, and instill in them the confidence to present and lead. Make the CovertSwarm North America Hive the place where the world’s best hackers want to work, grow their capability and never want to leave. 

• Collaborate globally – Work with CovertSwarm’s UK and global leadership to ensure we operate as one unified Swarm. Share tactics, align on strategy, and contribute to the overall direction of our services. You will have a seat at the table influencing our global offensive strategy. 

What You Bring 

• Proven red team leadership – You have built, led, and scaled offensive security teams. Maybe you grew a Red Team from a handful of testers to a robust operation, or you have led complex, multi-faceted attack campaigns. You know what it takes to make a team of hackers tick — and succeed. 

• Offensive security mastery – Deep expertise in the art and science of cyber-attack. You understand the full kill chain: phishing, web app exploits, cloud pivots, Wi-Fi hacking, physical intrusions, social engineering, and more. You might not write every payload yourself, but you can strategize and review them in your sleep. 

• Strategic vision with a hands-on edge – You can set high-level strategy and dive into the weeds when needed. You are as comfortable planning a 12-month offensive roadmap as you are brainstorming the exploit technique for a tricky engagement. 

• Mentor and team builder – A passion for people development. You have mentored hackers into senior roles and perhaps grown some into managers. You find joy in seeing your team members shine and grow under your guidance. 

• Stellar communicator – You can distill complex attack narratives into crystal-clear, non-jargon language for executives. Boardrooms do not scare you – you thrive in them, educating leaders on risk with persuasive storytelling. (If you can explain a RCE exploit to a CEO without their eyes glazing over, you are our person.) 

• Ambitious and accountable – You set audacious goals and deliver. 300% growth does not faze you; it fuels you. You take ownership of outcomes, hold yourself and your team to high standards, and you do not make excuses – you make it happen. 

• Culture fit (Rebel at heart) – CovertSwarm has no room for corporate politics – we value radical candor and agility. You are a team player with a sense of humor, and you know this mission is bigger than any one ego. (If you are just chasing a title or a fat paycheck, we are not for you.) 

Why CovertSwarm? 

• Pure offense, no fluff – We do one thing, and we do it best: adversary simulation. 100% of our focus is on hacking and attacking (ethically, of course). No dull compliance audits or defensive slide decks to slow you down. 

• Explosive growth and opportunity – Join a rocket ship. CovertSwarm’s client base and team are scaling at an insane rate (we are talking triple-digit growth). This role is your chance to ride that momentum and own the offensive security arena in the Americas. 

• Remote and flexible – Work from anywhere in the U.S. and design your own schedule. We care about results, not punching a clock 9–5. Need to take a mid-day break or work late? Cool with us, just get the job done well. 

• Unlimited PTO and training – Burnout is the enemy. Take time off whenever you need – no one is counting days. Want to attend training, get a cert, or spend a week researching a new exploit technique? Go for it. We invest heavily in continuous learning and development. 

• Team of All-Stars – You will be leading some of the most talented and passionate hackers in the industry. This is a team that lives and breathes offensive security, constantly sharing knowledge and pushing each other to new heights. We even go to DEFCON every year. 

• No mundane reports – Ever spent weeks writing a 100-page pentest report nobody reads? Not here. We built our own platform to deliver findings in real-time, so you never have to waste time on mind-numbing reports. Focus on the fun part – hacking – and let our tech handle the rest. 

• All the best toys – Need a new piece of kit or custom tool to pwn a client? You have got an expense account for that. Hardware, software, antennas, lock picks – whatever you require to be effective, we’ve got your back. We remove the roadblocks so you can be creative. 

• Community and credibility – We encourage our Swarm to contribute to the security community. Want to speak at Black Hat, DEFCON, or OWASP chapters? We will cover your expenses, pay you a bonus and support you. Our brand opens doors – as the Head of Adversary Simulation, you will be a visible thought leader. 

• No BS Culture – Leave your suit and tie at home. We pride ourselves on having fun, staying radically candid, and delivering killer results without corporate drama. Even our board members are hackers, so you’ll never have to justify your tactics to a clueless exec – leadership gets it. We’re all here to hack and make a difference, nothing else. 

Ready to Join the Swarm? 

Ready to unleash your expertise and lead the most relentless Red Team in the industry? This is your chance to be the hero who redefines offensive security across North America. If you’re up for the challenge, join CovertSwarm and let’s make history together. Your mission awaits.