Retained CISO Advisory

Security leadership that's in the room every week, not just during audit season.

A named CISO, embedded in your team — for regulated companies that need real security judgment now, and can't yet justify a $300K+ full-time hire.

Same leader, every week — not just during audit season.

The gap this fills

Most companies don't need a full-time CISO. They need the instincts of an experienced one, without the overhead of one.

Board members ask security questions. Enterprise buyers send 40-page vendor security questionnaires. HIPAA and SOC 2 audits don't wait for budget cycles. Most growth-stage companies are stuck between doing nothing and a hire they can't justify yet — so the work falls to a CTO or general counsel who has a full-time job already.

Full-time CISO

Total comp$300K–$400K+/yr
Time to hire4–9 months
Commitment5 days/week, indefinite
Right-sized forMature security org

Retained, embedded

Monthly retainer$6K–$20K/mo
Time to startUnder 2 weeks
Commitment1–3 days/week, scoped
Right-sized forBuilding the program

How engagements work

Three ways to bring in a security leader, scaled to where you are.

Advisory
Custom
4–6 hours/week

  • Strategic guidance and board prep
  • Vendor security questionnaire support
  • Policy and framework review
  • Direct line for ad hoc questions

Best for: pre-Series B companies fielding their first real security questions.

Program
Custom
2–3 days/week

  • Full security program ownership
  • Audit leadership (HIPAA, SOC 2, HITRUST)
  • Compliance and privacy officer functions, where one leader covers the full regulatory posture
  • Vendor and third-party risk management
  • Recurring board and executive reporting
  • Available for incidents as they happen

Best for: regulated, scaling companies treating security as core infrastructure, not a checkbox.

Every engagement starts with a two-week scoping sprint, so pricing reflects your actual environment — not a guess. Ask for a quote based on what you actually need.


Why embedded, not a project

A security assessment tells you where you stand today. A retained CISO is there for what happens next.

In your tools, not on the sidelines

Works inside your existing IT, MSP, and SOC relationships rather than replacing them — in your meetings, your Slack, your incident channel.

Real authority, not a deck

Owns the security roadmap and represents it directly to your board — not a one-time presentation that gets filed away.

Built for the moments that matter

Present for the vendor questionnaire holding up a deal, the board update before a raise, and the incident that doesn't wait for business hours.


Beyond security

Security, compliance, and privacy don't have to be three separate hires.

Most regulated companies need all three functions, but can't justify three full-time leaders — or three different vendors who don't talk to each other. One retainer can cover all three, backed by the certifications behind each.

CISO

Security leadership

Risk management, security architecture, vendor security reviews, and incident response — owning the program, not just advising on it.

CISSP · CCSP
CCO

Compliance leadership

Audit readiness, regulatory reporting, and program ownership across HIPAA, SOC 2, and the frameworks your auditors and board actually ask about.

CIPP/US · CIPT
CPO

Privacy leadership

Privacy-by-design, data protection strategy, and breach response planning — the function regulators expect someone to actually own.

CIPP/US · CIPT

Led by Chris Bowen, CISSP, CCSP, CIPP/US, CIPT

16+ years building security and privacy programs inside regulated companies.

Before Bowen & Company, Chris led security, risk, and compliance through two healthcare technology companies from early stage through scale — work that now sits behind every retained engagement.

$68M
ARR scaled at ClearDATA under his security leadership
50,000+
physicians secured across the DirectClarity network
16+ yrs
in healthcare security, privacy, and GRC
Zero
reportable breaches across that work
Before you book a call

A few things worth knowing up front.

Does this replace our IT team or MSP? +

No. A retained CISO sets direction and owns accountability for the security program; your IT team or MSP keeps doing the operational work. The two roles are complementary, not competing.

How fast can you start? +

Most engagements begin within two weeks of signing, starting with a scoping sprint to map your environment, existing tools, and immediate priorities before settling on a retainer.

What if we outgrow this and need someone full-time? +

That's a good outcome, not a lost client. Chris has built full security and privacy organizations from the ground up before and can help structure the role, write the job description, and support a clean handoff.

Do you only work with healthcare companies? +

Healthcare is the deepest bench of experience, but the same judgment applies across regulated industries — fintech, insurance, and other compliance-heavy spaces.

How is this different from your HIPAA Security Risk Assessment service? +

A Security Risk Assessment is a point-in-time deliverable — a defined scope, a report, a clear end date. A retained CISO engagement is ongoing leadership. Some clients start with an SRA and move into a retained relationship once they know what needs fixing. Risk assessments are handled separately through Bowen & Company.

Let's talk

Let's talk about what your security program actually needs.

Book a 20-minute call