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Post-Quantum Cryptography (PQC) Crypto-Agility Selling to the CISO and Chief Cryptographer — 60-Min Training

👁 0 views📖 1,145 words⏱ 5 min read5/30/2026

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Post-Quantum Cryptography (PQC) Crypto-Agility Selling to the CISO and Chief Cryptographer is a 60-minute training for AEs, SEs, and channel managers running $150K–$1.8M ACV cycles against incumbents like DigiCert, Entrust, PQShield, Crypto4A, ISARA (Quantinuum), InfoSec Global, Cellcrypt, Fortanix, Sectigo, AppViewX CERT+, and Venafi (CyberArk).

The session teaches sellers to qualify against the three-buyer reality (CISO, Chief Cryptographer, Compliance Officer), run a structured discovery on harvest-now-decrypt-later (HNDL) risk economics, demo against the customer's actual cryptographic inventory, and trap-set the multi-year renewal at month 18.

Built on MEDDPICC, Force Management's Command of the Message, and Andy Paul's "Sell Without Selling Out" discovery cadence.


Section 1 — Why Post-Quantum Cryptography Selling Is Different (5 min)

Open the room by killing the SaaS-seller default. PQC selling is regulator-driven and physics-driven. The National Security Memorandum 10 (NSM-10) and OMB Memorandum M-23-02 require federal agencies to inventory cryptography by 2024 and migrate by 2035. NIST FIPS 203, 204, 205 finalize the new algorithms.

Set the frame on the whiteboard.

End the segment with Mark Roberge's rule: *"Sell the crypto-agility platform, not the algorithm selection."*


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

  1. Opening (3 min): "Walk me through your cryptographic inventory project — algorithms in use, key sizes, certificate counts, code-signing posture."
  2. Cryptographic inventory baseline (10 min): "Have you completed an NSM-10-style inventory? Most enterprises discover 30%+ more cryptographic assets than they inventoried."
  3. HNDL exposure baseline (10 min): "What's your highest-sensitivity data — 20-year defense, healthcare, IP? That data is at active HNDL risk today."
  4. PQC algorithm coverage (10 min): "Which NIST PQC algorithms do you need supported — CRYSTALS-Kyber for key exchange, CRYSTALS-Dilithium for signatures, SPHINCS+ for stateless signatures, FALCON for compact signatures?"
  5. Crypto-agility posture (8 min): "Can your application stack swap cryptographic algorithms without code changes? Crypto-agility middleware is the modern bar."
  6. Certificate management posture (7 min): "How many TLS certificates are under management? PQC migration touches every certificate."
  7. Renewal posture (5 min): "When is your current PKI or certificate management contract up? What contractual extraction friction would we navigate?"
flowchart TD A[AE Schedules 60-Min Discovery] --> B[Send Pre-Brief 24 hrs Prior] B --> C{CISO + Cryptographer + Compliance?} C -->|No| D[Reschedule No Exceptions] C -->|Yes| E[Inventory + HNDL Exposure 20 min] E --> F[PQC Coverage + Crypto Agility 18 min] F --> G[Cert Mgmt + Renewal 12 min] G --> H[Confirm POC Scope Workshop] H --> I[Crypto-Agility POC Connected Within 14 Days] I --> J[Joint Cryptographer Review at Day 30] J --> K[Bind Decision at Day 60]

Section 3 — The POC That Wins (15 min)

Failure modes to ban. Algorithm-demo POCs without crypto-agility. Single-app POCs. No HNDL-exposure assessment.

Wins to coach. Crypto-agility middleware deployed. Walk through DigiCert's and PQShield's published POC agendas — both deploy crypto-agility middleware that allows swapping algorithms without app rewrites. HNDL-exposure assessment delivered. Map customer data classifications to HNDL risk windows.

NIST PQC algorithm interoperability tested. Run interoperability tests across CRYSTALS-Kyber, CRYSTALS-Dilithium, SPHINCS+, and classical algorithms in hybrid mode.

End with Andy Paul's rule: *"Show the customer their HNDL exposure reduced, not your algorithm count expanded."*


Section 4 — Handling the Incumbent Trap (10 min)

The room will face DigiCert, Entrust, and Venafi in eight of ten enterprise deals. Coach the room on three counter-moves.

Counter-move 1 — The crypto-agility depth wedge. Ask the Chief Cryptographer: *"Does your incumbent's platform support runtime algorithm swap without app rewrites? PQShield and DigiCert lead crypto-agility."*

Counter-move 2 — The hybrid-mode wedge. Ask: *"Does your incumbent support hybrid-mode certificates — classical + PQC algorithm — for compatibility during migration? Sectigo and DigiCert publish hybrid-mode pilots."*

Counter-move 3 — The certificate-volume wedge. Ask the CISO: *"How many certificates does your incumbent manage today? PQC migration multiplies certificate operations 3–5x. Throughput matters."*

Show Force Management's command-of-the-message rule: *"Displace on crypto-agility depth, not on algorithm count."*


Section 5 — Pricing Conversation and Procurement (10 min)

Landmine 1 — Per-cert vs. Per-platform pricing. Per-platform scales with migration; per-cert punishes scale.

Landmine 2 — Multi-year discount math. Three-year deals justify 12–18% discount; five-year deals justify 22–28%.

Landmine 3 — The procurement-only meeting. No procurement-only rule — refuse procurement-only meetings.

flowchart TD A[Joint CISO + Cryptographer + Compliance] --> B[Per-Platform Proposal Issued] B --> C{Multi-Year Discount Aligned?} C -->|No| D[Reset to Retention Math] C -->|Yes| E[MSA + SOW Drafted] E --> F{Procurement Solo Meeting?} F -->|Yes| G[Refuse Insist on Cryptographer Joint] F -->|No| H[Joint Negotiation Session] G --> H H --> I[Onboarding Within 14 Days] I --> J[HNDL Exposure Scorecard Month 1] J --> K[Quarterly Cryptography Review]

Section 6 — The Trap-Set for Renewal at Month 18 (5 min)

Trap-set 1 — Cryptographic inventory completed within 90 days. The number is the renewal narrative.

Trap-set 2 — Crypto-agility middleware deployed within 9 months. Lock in the architectural commitment.

Trap-set 3 — Hybrid-mode certificate pilot live within 12 months. Below 50% coverage is renewal-risk red.

Trap-set 4 — Joint regulator-readiness dashboard in QBR. Build the NSM-10-style dashboard into the QBR. By month 18, the dashboard is the renewal narrative.

Close the session by reading Jeb Blount's rule from *"Fanatical Prospecting"*: *"The renewal is sold on day one."*


FAQ

Should we lead with inventory or with algorithm migration? Lead with inventory — most enterprises have not completed an NSM-10-style inventory. Without it, the migration timeline is unknowable.

How do we handle a customer mid-DigiCert or Entrust renewal? Run a complementary crypto-agility deployment in a non-overlapping area. Build proof for the displacement conversation at renewal.

What is the right POC size for a Tier-1 enterprise? 60–90 days, crypto-agility middleware in one production app, hybrid-mode certificates tested.

How do we price against DigiCert's market-leader positioning? DigiCert wins on certificate breadth; we win on crypto-agility depth and PQC interoperability. Position complementary at the entry tier.

What if the customer asks us to integrate with their existing PKI, KMS, and HSM? Yes — every modern PQC platform integrates with Microsoft AD CS, AWS KMS, HashiCorp Vault, Thales Luna, Entrust nShield. Demo live in the POC.

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