Executive risk insurance should be engineered for pressure. Most programs are not.
Executive risk programs are rarely tested until a real disruption forces the question. I pressure-test them before that happens. Cyber, D&O, EPL, crime, professional liability. Different coverage. Same structural vulnerabilities.
For Canadian mid-market organizations that want more than a standard renewal exercise.
Strategic executive risk advisory. From assessment through placement.
The Approach
Insurance programs should be stress-tested the same way leadership teams stress-test business plans.
Most executive risk programs are purchased on precedent. Last year's limits. Last year's structure. Last year's assumptions about what could go wrong. The business changes every year. The insurance rarely keeps pace.
I take a different approach. I start with how disruption actually unfolds. Operationally. Financially. Legally. Then I work backward into the insurance structure to find where it holds and where it breaks. The goal is not to sell a policy. The goal is to make sure the program survives contact with reality.
When gaps are identified, I do not hand you a report and walk away. I structure the solution and place it in the market through direct carrier and MGA relationships.
A cyber event that shuts down operations. A governance dispute that gets personal. A crime loss that bypasses every control. The coverage lines are different. The question is always the same: does the structure hold under real pressure?
Executive Risk Lines
Specialist advisory across the full executive risk spectrum.
Each line carries distinct exposures. All share the same structural question: does the program hold under real pressure?
Operational disruption, business interruption, ransomware response, limit erosion under competing claim costs.
Explore Cyber Risk Advisory→Personal exposure for board members and executives, Side A reliance, shared limit fragility, regulatory and securities risk.
Explore Management Liability Advisory→Wrongful termination, discrimination, harassment, whistleblower claims, and the escalation path from HR to boardroom.
Social engineering fraud, employee dishonesty, funds transfer fraud, and the coverage gaps that surface when loss mechanics do not match policy triggers.
Personal liability for fiduciary decision-makers. Benefit plan administration failures, regulatory compliance gaps, and the exposure that comes with managing other people's financial interests.
Errors, omissions, and negligent acts in professional service delivery. Coverage structure review against real client dispute scenarios.
Extortion response, crisis management, and duty-of-care obligations for organizations with international operations, travel exposure, or high-profile leadership.
Not every organization needs every line. The conversation starts with understanding which exposures are material to your business.
Advisory Practices
Go deeper on the two executive risk lines where structural gaps are most common and most costly.
These advisory practices include free interactive tools, real-world case analysis, and detailed stress-testing frameworks. Additional executive risk lines are covered through the same advisory process.
Operational and financial disruption.
Your cyber limit has to cover ransom, incident response, legal, and business interruption from the same pool. I pressure-test whether the structure survives that collision.
- Business interruption exposure modeling
- Limit erosion analysis (the 35% benchmark)
- Free 60-second exposure calculator
Governance and people disruption.
When a governance dispute or employment claim escalates, defense costs, personal exposure, and parallel proceedings compete for the same program. I pressure-test whether D&O and EPL are built for how disputes actually develop.
- Individual protection and Side A analysis
- Defense cost velocity and limit erosion
- Free interactive governance risk scorecard
The Advisory Lens
What makes this different from a standard broker conversation.
A larger limit does not fix a structural problem. I focus on how the program behaves under pressure, not just how much coverage exists on paper.
I model realistic disruption scenarios and work backward into the insurance structure. Not the other way around. This surfaces gaps that traditional benchmarking misses.
I bridge the gap between technical risk and financial consequence. Whether the conversation involves your IT team, your legal counsel, or your board, I translate complexity into language that supports executive decisions. No jargon. No black boxes.
Every engagement ends with clear findings designed for executive decision-making. Not a 50-page report. Not a coverage spreadsheet. Actionable intelligence you can take to the board.
Is This For You
Best fit for organizations where executive risk decisions carry real consequence.
This advisory practice is designed for Canadian mid-market organizations with $5M to $500M in revenue, active boards or advisory boards, material operational or governance complexity, and leadership teams that want structural clarity across their executive risk program. Whether the exposure is cyber, management liability, crime, professional liability, or a combination, the approach is the same: stress-test the structure before a claim does. If your organization has outgrown its insurance program but has never pressure-tested whether the structure still fits, this is the conversation to start.
Why Work With Cameron
Cameron Baker
CIP, CC
I help leadership teams understand what their executive risk insurance will, and will not, actually cover before a claim forces the conversation.
I specialize in executive risk and cyber insurance advisory, helping leadership teams understand whether their coverage is structured for the exposures they actually carry. I hold both the CIP (Chartered Insurance Professional) designation and the CC (Certified in Cybersecurity) credential from ISC2. That combination gives me a perspective most brokers in this space do not have: the ability to bridge technical risk and financial exposure, and translate both into insurance structure that actually holds up under a claim.
Advising CFOs, boards, and risk leaders at Canadian companies from $5M to $500M in revenue.
The Process
How It Works
Book a 30-Minute Conversation
I review your organization's risk profile, current coverage structure, and the areas that matter most to your leadership team. No preparation needed on your end.
Receive a Tailored Assessment
I analyze your program against realistic disruption scenarios, whether operational, governance, or people-driven, and identify where the structure holds and where it does not.
Make Informed Decisions
You receive clear, actionable findings designed for executive and board-level decision-making. If structural gaps exist, I outline options, present market alternatives, and structure the program through direct carrier and MGA relationships. You decide how to move forward.
Know whether your executive risk program protects leadership the way the board expects. Before a claim proves it does not.
Book a confidential risk conversation to review your cyber, D&O, EPL, crime, or professional liability structure, identify pressure points, and understand where gaps may exist.
Call directly for an immediate conversation.
Send an email anytime.
Responses within one business day.