Our Speakers
An Uncompromising Roster of Experts.
Our speakers bring unfiltered, tactical insights forged in the crucible of real-world incident response.

Brian Blakley
CISO, ConnectSecure & Bellini Capital
ConnectSecure
Brian Blakley brings over 30 years of real-world leadership in information security and business strategy, shaped by a hands-on career building, growing, and successfully exiting multiple MSPs. As a seasoned executive, board advisor, and entrepreneurial force, Brian knows the MSP grind intimately and he’s made it his mission to help MSPs shift from "just IT guys" to indispensable business risk advisors and revenue protectors.
From landing a company on the INC 500 list with 1,200% growth, to guiding enterprises through complex infosec and compliance journeys, Brian blends street-smart business acumen with elite certifications like CISSP, CISM, CISA, CRISC, CMMC-CCP, and Certified CISO. His approach centers on translating technical risk into language that boards, executives, and business owners understand, bridging the gap between cybersecurity strategy and revenue protection.
Today, Brian advises MSPs, SaaS companies, and mid-market organizations on how to turn compliance and security into growth engines. He mentors founders and serves as the driving force behind scalable, audit-ready security programs. His deep experience includes roles as a full-time and fractional CISO, risk assessor, compliance strategist, and trusted M&A advisor.
Above all, Brian is passionate about helping MSPs thrive. Having walked in their shoes, he understands what it takes to deliver outcomes, earn trust, and win business in a crowded, commoditized space. At Right of Boom 2026, he’s here to equip attendees with fresh, actionable insights on transforming security and compliance into powerful differentiators.
Sessions
Tue Feb 02, 8:00 AM - 5:00 PM
Intro to Certified Cybersecurity Leadership Stratregist (CCLS) Course - Lunch Included ($299)A One-Day Introduction to the Certified Cybersecurity Leadership Strategist (CCLS) Program. This qualified for 8 hours of CPE credits. Attendees will receive a $500 discount on a future CCLS course purchase.
Your team identified the risk. You showed the client the evidence. You recommended a solution. So why did your client still say no?
For many MSPs and MSSPs, identifying cyber risk is not the hardest part. The real challenge is helping clients understand what that risk means to the business, prioritize the right outcomes, and commit to a sound risk-management strategy. Too often, security conversations become discussions about tools, QBR recommendations feel like sales pitches, and technically solid proposals stall because clients can’t connect them to downtime, revenue, liability, or business resilience.
That credibility gap does more than weaken security outcomes. It creates friction with clients, slows the growth of consulting and advisory services, compresses margins, and increases exposure when a deferred risk becomes a real incident.
This one-day pre-conference experience introduces the leadership mindset at the foundation of the Certified Cybersecurity Leadership Strategist (CCLS) program. It is designed for MSP and MSSP professionals who advise clients, influence executive decisions, or lead security strategies. This includes engineers moving into advisory roles, experienced vCISOs, and established security leaders. It assumes you already know the technology; the work here is learning to think, communicate, and decide like a business executive.
Participants will explore why good recommendations fail, how business leaders actually evaluate cyber risk, and what separates a technical presenter from a trusted strategic advisor. The session also addresses one of the most overlooked capabilities in vCISO engagements: building consensus before making the formal ask.
Effective security leaders do not enter an executive meeting simply hoping for approval. They engage stakeholders beforehand, understand their priorities and concerns, build alignment, and arrive prepared to address the questions that could otherwise derail the decision.
This is not a condensed version of the three-day CCLS certification, and it is not a shortcut to a vCISO title. It is a purposeful introduction designed to reveal where technical language, tool-first conversations, and weak business framing may be limiting your influence and undermining client confidence.
You will leave better prepared to turn security findings into meaningful business conversations, strengthen client trust, and guide recommendations toward informed decisions instead of another deferred project.
This one-day session delivers practical, standalone value and serves as the recommended foundation for the full CCLS program. It is offered both in person and as an online recording, so it can scale as the standard on ramp to CCLS and it is not a barrier to entry: the full certification remains open to direct registrants, and current alumni will be given access to the material. During the three-day CCLS certification experience, these capabilities are fully developed through proven frameworks, individual coaching, executive simulations, budget-defense exercises, crisis leadership scenarios, and board-level practice.
This course requires purchase of the Intro to CCLS ticket for $299 (includes lunch).
Thu Feb 04, 1:30 PM - 2:15 PM
The Next Generation vCISO: What the Role Looks Like in 2030 and what it needs to look like today to be successful?The CISO role is undergoing its most significant transformation in history shifting from technical guardian to business executive and from reactive defender to proactive strategist. This session forecasts what the CISO role will demand over the next few years, what skills today's security leaders must develop now, and how organizations should be rethinking the security leadership function to stay competitive and resilient.
Thu Feb 04, 4:45 PM - 5:30 PM
From Technician to Executive: The Language Shift That Changes EverythingSecurity leaders are losing the budget battle not because they lack expertise — but because they're speaking the wrong language. This session breaks down the exact communication shift required to move from technical reporting to executive influence, showing you how to reframe risk in terms of revenue, resilience, and business continuity that boards and C-suites act on immediately.
Fri Feb 05, 8:30 AM - 9:15 AM
From Technician to Executive: The Language Shift That Changes Everything (Repeated)Security leaders are losing the budget battle not because they lack expertise — but because they're speaking the wrong language. This session breaks down the exact communication shift required to move from technical reporting to executive influence, showing you how to reframe risk in terms of revenue, resilience, and business continuity that boards and C-suites act on immediately.



