CISOs are the hardest buyers in B2B to reach with cold outreach. They receive 50-100 vendor attempts per month, have delegated email to assistants, and have learned to ignore LinkedIn messages that begin with "I'd love to connect." The only outbound that earns their attention is outreach that demonstrates specific knowledge of their environment -- and an event invitation that addresses a real priority they are dealing with right now.
Clay makes it operationally possible to build that level of specificity at scale. Here is the exact workflow.
Step 1: Build Your CISO Target List
Start with LinkedIn Sales Navigator or Apollo:
- Title: CISO, Chief Information Security Officer, VP of Information Security
- Company: 500-10,000 employees (CISOs at smaller companies manage too many functions to be single-vendor buyers; at larger companies, procurement is too layered for direct CISO engagement)
- Industry: Focus on one vertical per campaign (fintech, healthtech, cybersecurity vendors, enterprise SaaS)
- Geography: US (or target region)
For a 90-day event campaign, 200-400 CISO contacts is the right scale.
Step 2: Import Into Clay and Run Enrichment Waterfall
Import your LinkedIn or Apollo export into Clay as a table. Set up these enrichment columns:
Company enrichment:
- Company description (from Clearbit or LinkedIn)
- Recent news (Claygent web research: "site:news.ycombinator.com OR site:techcrunch.com OR site:bleepingcomputer.com [company name] security breach incident 2025 2026")
- Open security job postings (Claygent: "site:linkedin.com/jobs [company name] CISO security engineer")
- Technology stack signals (BuiltWith or similar for tech companies)
Contact enrichment:
- Professional email (waterfall: LinkedIn > Apollo > Hunter.io)
- LinkedIn headline and summary (for recent activity signals)
- Recent LinkedIn posts (Claygent: scrape last 3 posts for topic signals)
Step 3: Score and Prioritize With Signals
Use a Clay formula column to score each CISO account:
Tier 1 signals (score +3 each):
- Company had a security incident or data breach in last 12 months
- CISO is newly appointed (in role less than 12 months -- new leader, fresh priorities)
- Company raised a funding round in last 6 months (new security budget often allocated)
- Open CISO or Head of Security search (existing CISO may be leaving -- transition creates urgency)
Tier 2 signals (score +1 each):
- Company is in the same regulatory framework as your event topic (HIPAA, PCI, SOX)
- Company has open security engineering roles (indicates active security investment)
- CISO has posted about security topics on LinkedIn in last 60 days (content-active, more receptive)
Focus event outreach on Tier 1 accounts (score 3+). Run Tier 2 accounts through email sequences.
Step 4: Generate Personalized Event Invites With Claude
Add a Claude AI column in Clay. For each CISO, run this prompt template:
"Write a 3-sentence LinkedIn invite from a senior cybersecurity leader to [CISO name], CISO at [company]. Context: [paste Claygent news summary and job posting signals]. The invite is for a live virtual roundtable on [event topic] with [speaker name and credentials]. Reference one specific, credible detail from the context. Tone: peer-to-peer, not vendor-to-prospect. No buzzwords."
This generates a customized invite for each of your 200-400 CISOs in under 2 hours. Quality-check a sample of 15-20 before batch-sending.
Step 5: Deliver the Invites and Track Engagement
Export from Clay to Apollo for sequenced delivery:
- Day 1: LinkedIn connection request (no message)
- Day 2: LinkedIn message with personalized event invite
- Day 5: Email with event details and speaker bio
- Day 9: Email follow-up (final reminder, 3 spots remaining)
In Apollo, tag CISO accounts that:
- Accept the LinkedIn connection (warm signal)
- Open the email 2+ times (high intent)
- Register for the event (hot account -- immediate follow-up priority)
LinkedOtter manages this end-to-end for cybersecurity vendors -- building the Clay enrichment table, running the Claude personalization, and executing the follow-up sequence that generates 43 qualified meetings in 60 days. See event proof and pricing.