AI Safety / Red Team Services Selling to the CISO — 60-Min Training

Question

Pulse RevOps · The Machine · Accepted Answer

### Direct Answer

> **AI Safety / Red Team Services Selling to the CISO** is a 60-minute training for AEs running $50K–$1M ACV cycles against **HiddenLayer, Lakera, ProtectAI, Robust Intelligence, Cranium AI**. Qualify against **CISO + Head of AI + Compliance**, run discovery on **OWASP LLM Top 10 coverage + multi-modal probing + frontier-vendor partnership**. Built on **MEDDPICC** + **Force Management**.

---

## Section 1 — Why AI Safety Services Selling Is Different (5 min)

AI safety is **regulator-and-incident-driven**. Customers buy after a near-miss or regulator pressure.

End with **Mark Roberge's** rule: *"Sell findings + defense + retainer cadence."*

---

## Section 2 — The 60-Minute Discovery (15 min)

> 1. **Opening (3 min):** "Walk me through your production AI systems and any past incidents."
> 2. **OWASP LLM Top 10 self-score (10 min):** "Which categories are highest risk?"
> 3. **Existing red-team activity (10 min):** "Who's tested your AI today?"
> 4. **Multi-modal AI scope (10 min):** "Image, audio, video AI exposure?"
> 5. **Frontier-vendor partnership (8 min):** "Anthropic, OpenAI, Google formal partnerships?"
> 6. **Compliance posture (7 min):** "EU AI Act, NIST AI RMF, SOC 2 + AI."
> 7. **Renewal posture (5 min):** "Existing retainers?"

```mermaid
flowchart TD
    A[AE Schedules Discovery] --> B[Pre-Brief Sent]
    B --> C{CISO + Head of AI + Compliance?}
    C -->|No| D[Reschedule]
    C -->|Yes| E[OWASP + Past Activity 20 min]
    E --> F[Multi-Modal + Partnerships 18 min]
    F --> G[Compliance + Renewal 12 min]
    G --> H[Scoping Workshop Within 5 Days]
```

---

## Section 3 — The Scoping That Wins (15 min)

**Failure modes to ban.** Generic OWASP coverage. No multi-modal. No retainer roadmap.

**Wins to coach.** **OWASP-Top-10 coverage matrix.** **Multi-modal probing demo.** **Retainer-with-quarterly-cadence proposal.**

End with **Andy Paul's** rule.

---

## Section 4 — Handling the Incumbent (10 min)

**Counter-move 1 — OWASP coverage wedge.** *"What % of OWASP LLM Top 10 does your incumbent cover?"*

**Counter-move 2 — Multi-modal wedge.** *"Image + audio jailbreak probing?"*

**Counter-move 3 — Frontier-vendor partnership wedge.** *"Formal Anthropic, OpenAI, Google partnership?"*

---

## Section 5 — Pricing Conversation (10 min)

**Landmine 1 — One-shot engagement.** Push retainer.

**Landmine 2 — Multi-year discount.** 10–15% for 3-year retainer.

**Landmine 3 — No procurement-only meetings.**

```mermaid
flowchart TD
    A[Joint CISO + AI + Compliance] --> B[Retainer Proposal]
    B --> C{Multi-Year Aligned?}
    C -->|No| D[Reset]
    C -->|Yes| E[MSA Drafted]
    E --> F{Procurement Solo?}
    F -->|Yes| G[Refuse]
    F -->|No| H[Joint Negotiation]
    G --> H
    H --> I[Engagement Kick-off 7 Days]
    I --> J[OWASP Scorecard Month 1]
    J --> K[Quarterly Retainer Renewal]
```

---

## Section 6 — The Trap-Set for Renewal at Month 12 (5 min)

**Trap-set 1 — Quarterly probing cadence delivered.**

**Trap-set 2 — OWASP Top 10 100% coverage.**

**Trap-set 3 — Frontier-vendor partnership demonstrated.**

**Trap-set 4 — Joint CISO dashboard in QBR.**

Close with **Jeb Blount's** rule.

---

## FAQ

**HiddenLayer or Lakera?** HiddenLayer broad AI defense; Lakera guardrail-API-first.

**Quarterly or annual retainer?** Quarterly.

**Multi-modal coverage critical?** Yes — rising attack surface.

**Frontier-vendor partnership matters?** Yes — drives inbound + credibility.

**Penalty per OWASP gap?** Renewal contests.

## Sources

- OWASP — Top 10 for LLM Applications
- HiddenLayer — AI Defender Reference
- Lakera — Guard Reference
- ProtectAI — Recon Reference
- Robust Intelligence — AI Firewall Reference
- Force Management — MEDDPICC
- Mark Roberge — Sales Acceleration Formula
- Andy Paul — Sell Without Selling Out
- Jeb Blount — Fanatical Prospecting
- NIST AI RMF — AI Risk Management Framework

AI Safety / Red Team Services Selling to the CISO — 60-Min Training

Direct Answer

Section 1 — Why AI Safety Services Selling Is Different (5 min)

Section 2 — The 60-Minute Discovery (15 min)

Section 3 — The Scoping That Wins (15 min)

Section 4 — Handling the Incumbent (10 min)

Section 5 — Pricing Conversation (10 min)

Section 6 — The Trap-Set for Renewal at Month 12 (5 min)

FAQ

Sources

What does the score mean?