Sidewalk Security Advisors LLC provides fractional CISO leadership for regulated organizations that can't afford to guess about security risk—and can't justify a $250K+ executive to solve it.
Jeremy Krienke
Former CISO, Financial Services · Deloitte & Touche Alumni
Complimentary for qualified organizations · Limited to 3 per quarter
This is not:
An IT audit disguised as advisory
A 200-page report that collects dust on a shelf
A vendor trying to sell you tools and software
Checkbox compliance theater that won't survive an exam
This is:
A dedicated security executive who shows up for your team
Risk translated into the language your board and regulators speak
Actionable governance that holds up under regulatory scrutiny
A leadership partnership—carrying the weight of security with you, not handing you a binder
The cost of inaction
$3.31M
Average breach cost for organizations under 500 employees
25–40%
Insurance premium increase without a documented security program
60%
Of small businesses close within 6 months of a breach
Regulatory penalties, insurance gaps, board liability, and breach costs don't wait for budget season.
Who we serve
We work with leaders at organizations that are
Community Banks & Credit Unions
FFIEC, FDIC, and NCUA exam readiness and ongoing compliance
Board members and examiners expecting documented security governance
IT vendors who can't speak the language of business risk
Healthcare & Mission-Driven Organizations
HIPAA compliance and grant security requirements tightening
Donors and funders increasingly requiring evidence of security posture
A breach here threatens the mission, not just the margin
Startups & Growth-Stage Companies
Losing enterprise deals over unanswered security questionnaires
SOC 2 readiness and cyber insurance without a full-time hire
Investors asking about security posture during due diligence
Our approach
Replace with
Advisory context photo
Boardroom, review session, or
architectural abstract
Every engagement begins with understanding. Where you stand today, what your regulators and board expect, and what's actually at risk.
Executive Security Diagnostic
2 to 2.5 weeks
Executive interviews, governance review, compliance gap analysis, and a board-ready findings brief. You'll know exactly where you stand.
Strategic Roadmap
Delivered with findings
A prioritized security roadmap aligned to your business goals, regulatory requirements, and risk appetite. Clear actions, clear owners, clear timelines.
Ongoing Advisory or Fractional CISO
Monthly retainer
Sustained security leadership tailored to your needs. From quarterly strategic sessions to weekly embedded executive engagement. The scope scales to fit your organization.
Your Advisor
Former Chief Information Security Officer in the financial sector. Built and led security programs at state-chartered banks, advised growth-stage fintechs, and developed governance frameworks for organizations under regulatory pressure.
Before founding Sidewalk Security Advisors, I spent years at Deloitte & Touche helping organizations across government, finance, and manufacturing build and mature their security programs. I started this firm because too many regulated organizations are underserved by IT vendors who can't translate technical risk into the language boards and examiners need to hear.
Executive Security Diagnostic
Before we work together, we need to understand where you stand. Every engagement starts with a diagnostic that gives you clarity, not a pitch.
Executive interviews
Business context and risk tolerance, understood firsthand
Governance & compliance gap analysis
Measured against your applicable regulatory frameworks
Security posture review
Policies, controls, and operational maturity assessed
Board-ready findings brief
Prioritized recommendations with a clear path forward
Apply for your diagnostic
Limited to 3 engagements per quarter. We review every application personally.
We respond within 48 hours.