The CISO listened to my security product demo, then asked: "What happens when your platform gets breached and our data is compromised?"
Not "if." When.
I started explaining our security architecture, our encryption standards, our compliance certifications.
He interrupted: "Every vendor tells me they're secure. Then I read about breaches. SolarWinds was 'secure.' Okta was 'secure.' LastPass was 'secure.' They all got breached.
I'm not asking if you're secure. I'm asking: when you get breached—because everyone gets breached eventually—what's your incident response? How fast do you detect it? How do you notify us? What's our liability exposure?"
I'd come from traditional SaaS marketing where we sold optimization and efficiency. The pitch was: "We'll make you faster and better."
In cybersecurity, the pitch is: "We'll protect you from catastrophic loss, but we might fail, and here's what happens when we do."
That's a fundamentally different value proposition.
Why Cybersecurity PMM Is Unlike Any Other Category
After three years selling security products, I learned this industry operates on fear, skepticism, and proof:
You're Selling Insurance Against Disasters Buyers Hope Never Happen
Most SaaS products promise positive outcomes: more revenue, better productivity, happier customers.
Security products promise negative outcome prevention: no data breaches, no ransomware, no compliance failures.
This creates strange buyer psychology:
Buyers know they need security. But they hope they never find out if it works because that would mean they've been attacked.
It's like buying fire insurance. You need it. You pay for it. You hope you never use it. And you're skeptical it'll actually help when you need it.
This means buyers evaluate security products in a weird emotional state:
- Fear (of what happens if they get breached)
- Skepticism (that any product actually works)
- Fatalism (they assume they'll eventually get breached anyway)
I learned this in my first security deal when the buyer said: "Look, I know we're going to get breached eventually. I'm buying your product so when the breach happens, I can tell the board I did due diligence."
They weren't buying our product because they believed it would prevent breaches. They were buying it for CYA when the inevitable breach occurred.
This completely changes how you message:
Traditional SaaS messaging: "Our product delivers X outcome."
Security messaging: "When [disaster scenario] happens, our product ensures you're protected/compliant/informed."
The value proposition isn't "prevent all attacks" (nobody believes that). It's "when attacks happen, reduce the damage."
Trust Is Everything and Impossible to Establish
Security buyers need to trust you with their most sensitive data and systems. One mistake could destroy their business.
But they have zero reason to trust you.
They've watched established security companies get breached:
- RSA's SecurID tokens got compromised
- Security firm FireEye got hacked by nation-states
- Password manager LastPass had customer vaults stolen
- Authentication provider Okta had breaches
If the companies whose entire business is security get breached, why should anyone trust a startup?
Every security sales conversation includes this unspoken question: "What makes you different from all the security companies that failed?"
I tried establishing trust through credentials:
- Our team's security backgrounds
- Our compliance certifications
- Our penetration test results
- Our security architecture
Buyers appreciated this information. They didn't trust us.
What actually built trust: third-party validation and time.
Third-party validation:
- SOC 2 Type II reports (not just Type I)
- Independent security audits by firms buyers recognized
- Customer references from companies with mature security teams
- Integration partnerships with established security platforms
Time:
- Being in market for years without incidents
- Building a track record of responsible disclosure
- Demonstrating mature incident response
The hard reality: you can't fast-track trust in security. Buyers won't fully trust you until you've been around long enough to prove you haven't failed.
Our sales cycles with early-stage companies: 60 days. Our sales cycles with enterprises with mature security teams: 9-12 months.
The difference was trust-building time.
Technical Buyers Want to Test Everything
Security buyers don't trust vendor claims. They test everything themselves.
Every enterprise deal included:
Security questionnaire: 50-200 questions about our architecture, practices, incident response, compliance, data handling, employee vetting, audit logs, etc.
Penetration testing: They wanted to hire external firms to pen test our platform.
Architecture review: Their security architects reviewed our code, infrastructure, encryption methods, key management.
Compliance audit: They verified our SOC 2, ISO 27001, and other certifications directly with auditors.
Reference calls: They called our customers' CISOs to ask about real-world experience.
This due diligence took 3-6 months before they'd even consider purchasing.
I came from SaaS where demos and case studies were sufficient proof. In security, buyers assume you're lying until proven otherwise.
We built this into our sales process:
- Security questionnaire library (pre-answered common questions)
- Architecture documentation (detailed technical specs ready to share)
- Pen test permission and scoping (we facilitated their testing)
- Reference customer list (CISOs who'd talk to prospects)
This validation wasn't sales enablement. It was a mandatory gate before deals progressed.
Compliance Is Not a Feature, It's a Requirement
In most SaaS, compliance is a checkbox: "Are you SOC 2 compliant? Great, moving on."
In security, compliance is table stakes and buyers verify everything:
- SOC 2 Type II (not just Type I)
- ISO 27001
- PCI DSS (if handling payment data)
- HIPAA (if handling health data)
- FedRAMP (if selling to government)
- GDPR compliance
- State privacy laws (CCPA, etc.)
And they don't trust your claims. They want to see the actual audit reports.
We learned to provide full SOC 2 Type II reports (not just attestation letters) proactively. This was 100+ pages of detailed security controls and audit findings.
Most vendors fought sharing full reports. We made them available immediately because we knew buyers would eventually demand them anyway.
This built trust: "They're willing to show us everything, not just the summary."
The Threat Landscape Changes Constantly
In traditional SaaS, you build features and they stay relevant for years.
In security, new attack vectors emerge constantly. What worked six months ago might be useless today.
Buyers know this. They ask: "How do you stay ahead of emerging threats?"
Your product roadmap needs to demonstrate constant evolution:
- How are you adapting to new attack techniques?
- How do you respond when new vulnerabilities are discovered?
- How fast do you patch when threats emerge?
We built a public security changelog showing how we responded to emerging threats:
- "We implemented protection against the new XYZ attack vector within 48 hours"
- "We proactively patched the CVE-XXXX vulnerability before it was actively exploited"
This demonstrated security as an ongoing practice, not a fixed product.
What Actually Works in Cybersecurity PMM
After three years of failed pitches and lost deals, here's what works:
Lead With Incident Response, Not Attack Prevention
Don't promise perfect prevention. Promise effective response.
Bad messaging: "Our platform prevents 99.9% of attacks." (Nobody believes this, and the 0.1% that get through are catastrophic)
Better messaging: "When attacks occur, our platform detects them in under 5 minutes and automatically contains the threat before it spreads. Average time from detection to containment: 8 minutes vs. industry average of 277 days." (Assumes attacks will happen, focuses on damage limitation)
Security buyers know prevention is impossible. They buy tools that minimize damage when prevention fails.
Use Fear Appropriately (Real Scenarios, Not FUD)
Security marketing gets accused of FUD (fear, uncertainty, doubt). But fear is appropriate when the threats are real.
The difference:
FUD: "Hackers are everywhere and will destroy your business!" (Vague fear, no specifics)
Appropriate fear: "The average ransomware attack costs $4.5M in downtime, recovery, and ransom. Healthcare organizations face an average of 1,463 attacks per week. When Scripps Health was hit with ransomware, they spent $113M recovering. Here's how our platform would have limited that damage." (Specific scenario, real data, clear connection to solution)
We created "breach scenario" case studies:
"When [Company Type] faces [Specific Attack], here's what happens without protection vs. with our platform."
These scenarios used real attack techniques and real business impact data. They created urgency without being manipulative.
Build Competitive Intelligence Around Security Posture
Competitive positioning in security isn't about features. It's about security posture.
Traditional competitive battle cards compare features:
- ✓ We have SSO
- ✓ Competitor has SSO
Security competitive battle cards compare security practices:
- ✓ We've never had a customer data breach
- ✗ Competitor had a breach in 2023 affecting 40M users
- ✓ Our SOC 2 Type II shows zero control deficiencies
- ✗ Competitor's SOC 2 Type II had 3 control deficiencies
This feels harsh. It's also what buyers care about.
We tracked competitor security incidents, compliance findings, and architectural weaknesses. This wasn't FUD—it was documented public information that buyers needed to evaluate risk.
Managing detailed competitive intelligence about security incidents, compliance reports, and architectural vulnerabilities across 20+ competitors required systematic organization. I used tools like Segment8 to maintain updated battle cards with links to incident reports and compliance findings—critical for sales to have current information when buyers asked about competitor breaches.
Offer Transparent Security Documentation
Most vendors hide security details: "Contact sales for our security whitepaper."
We made everything public:
- Full architecture diagrams
- Encryption specifications
- Data flow documentation
- Incident response procedures
- Security changelog
- Vulnerability disclosure policy
This transparency built trust: "They're not hiding anything."
It also saved sales time. Security architects could review our docs before the first call and come prepared with specific questions rather than starting from zero.
Create Reference Customer Networks
Security buyers trust other security buyers more than they trust vendors.
We built a formal reference customer program:
- Customers agreed to take reference calls
- We matched prospects with similar companies/industries
- Customers shared real experiences, including problems
The honesty built credibility. When a reference customer said, "We had some implementation challenges but their team was responsive," it was more believable than a perfect case study.
We incentivized references with early access to new features and exclusive security briefings. This made participation valuable, not just a favor.
Demonstrate Security Competence Through Content
Security buyers evaluate your company's security competence, not just your product.
We published:
- Technical deep dives on attack techniques
- Analysis of major security incidents
- Security research findings
- Responsible disclosure reports
This content demonstrated that we understood security at a deep level.
When buyers googled our company, they found technical security content, not just marketing fluff. This built credibility before the first call.
The Unexpected Advantages of Security PMM
Despite the skepticism and long sales cycles, security has unique advantages:
Budgets are non-discretionary. Companies must invest in security. Even in recessions, security budgets stay funded.
Expansion revenue is strong. Once you protect one part of the environment, expanding to other areas is natural. Our net revenue retention was 135%.
Retention is high. Switching security tools is risky. Once you're protecting production systems, customers rarely switch. Our retention was 97%.
Urgency is real. When a company has a security incident or compliance deadline, they buy immediately. No 6-month deliberation.
Two years after that CISO asked "what happens when you get breached," I had a better answer.
Not: "We won't get breached because we're super secure."
Instead: "Here's our incident response timeline. Here's how we detected and contained our pen test simulations. Here's how we'd notify you. Here's our customer communication SLA. Here's our liability model. Here's our cyber insurance coverage. Here's our track record over three years with zero customer data breaches."
He bought.
Security marketing isn't about claiming invulnerability. It's about demonstrating competence, transparency, and effective response when things go wrong.
The playbook:
- Lead with incident response, not prevention promises
- Use real scenarios, not vague FUD
- Build trust through transparency, not marketing claims
- Let buyers test everything
- Create reference networks of trusted peers
- Demonstrate security competence through content
Security buyers are skeptical for good reasons. They've seen too many failures.
Meet their skepticism with proof, transparency, and realistic promises about what happens when attacks occur.
That's how you win in cybersecurity.