Built by an MSP owner who's been in the trenches for 30+ years
I get calls from MSPs and business owners who have just been breached and have no idea what to do next. Their techs are great at keeping things running day to day, but when it turns into an incident, they don't know how to respond, what to touch, what not to touch, or what to say to clients and carriers. After decades in the trenches as an engineer and MSP owner, I kept seeing the same problem: good MSPs selling great tools, but quietly carrying way too much risk inside their own house. I started SIREN and the SIREN Certified program to fix that. Over 12 weeks, I walk you through the same process I used to harden my own MSP—tightening our stack, cleaning up access and backups, building real first-responder playbooks, and creating offers clients actually understand and buy. This isn't theory or vendor slides; it's the working system I built for my business, now laid out step-by-step for yours.
The MSSP Playbook was written during a pivotal moment in the MSP industry. I wrote it to give MSP owners a clear, practical, and proven blueprint for evolving from a traditional IT support model into a true Managed Security Service Provider. The goal was simple: empower MSPs with the same tools, processes, and strategic thinking that high-performing security firms use every day, without the fluff, confusion, or vendor-driven noise that often clouds our industry.
When I published the Playbook, I had no idea it would take off like it did. It became a #1 International Best Seller across 14 countries, reaching MSPs around the world who were hungry for straightforward guidance on security, operations, packaging, pricing, and scaling. Years later, it continues to sell on Amazon and continues helping MSPs modernize their business model — a reflection of just how fast the cybersecurity landscape is shifting and how much clarity the industry still needs.
The Playbook remains relevant today because the core challenges MSPs face haven't changed:
These are the same challenges we address inside the SIREN peer group, where MSPs take the lessons from the book and implement them in real time. The book is the foundation — SIREN is the evolution. While the Playbook helps MSPs understand what to do, SIREN helps them execute how to do it with accountability, coaching, and a cohort of peers walking the same path.
This is why the MSSP Playbook continues to serve as the intellectual backbone of the SIREN Security community. The demand for resilient, security-minded MSPs has never been higher. The Playbook set the stage. SIREN takes MSPs the rest of the way.
SIREN Security was founded by Charles Henson, a career engineer turned MSP owner who has spent more than three decades building, securing, and scaling IT services for businesses that cannot afford to be down.
Charles started as a hands-on technician, crawling under desks, fixing outages at 2 a.m., and learning—one tough client at a time—what it really takes to keep networks safe and businesses running. Over the years, he grew that experience into a successful managed services practice, Nashville Computer, and then into SIREN Security, a focused initiative to help other MSPs secure themselves first and lead with confidence in security.
He is not a theorist. He is an operator who turned lessons from real incidents, real clients, and real pressure into systems MSPs can actually use.
Charles has lived the full MSP journey:
That arc means Charles understands exactly where most MSPs are stuck: good people, good tools, but too much risk inside their own house—and not enough structure to fix it.
Most MSPs are quietly carrying more risk than they realize.
Clients decline advanced security, then forget they declined it when an incident hits. Insurance applications are signed with the best of intentions, but the day-to-day reality inside the MSP does not always match the "conditions" in the policy. Larger clients show up with security questionnaires that feel just a bit beyond what your current processes can comfortably back up.
SIREN exists to change that.
The goal is simple:
Help MSPs secure themselves first, standardize how they do
security, and give their teams the tools, language, and playbooks to
act like first responders—not just tool resellers.
Charles is not just another "coach" talking about security from the sidelines. His credibility comes from a long list of real-world work, including:
Behind all of that is one constant: Charles still thinks like an engineer who has to make things work in the real world.
When you plug into SIREN Security, you are learning directly from Charles and the systems he uses and teaches:
If you are an MSP owner, operator, or security lead, you are being pulled in a hundred directions: sales, service, hiring, tools, and now deeper and deeper security expectations.
Charles has spent decades where you are now—and he has already done the hard work of turning experience into repeatable systems.
Working with SIREN means you are not guessing in the dark. You are learning from someone who:
SIREN Security is dedicated to one thing:
helping MSPs become security-led businesses that can withstand
real-world pressure—from clients, carriers, and attackers.
Through programs like SIREN Certified and the MSP First Responder training, Charles and the SIREN team work with MSPs to:
If you are serious about tightening your MSP's security and leading from the front, SIREN is built for you.
These principles guide every decision we make and every client relationship we build.
We tell you what you need to hear, not what you want to hear. Honest assessments and transparent recommendations.
We constantly refine our methodologies based on real-world results and emerging threats.
We understand the pressure you're under and the constraints you face. We work within your reality.
We don't settle for "good enough." Every client deserves our absolute best effort and expertise.
Whether you're just starting your compliance journey or looking to level up your existing security program, we're here to help.