The Cyber Sales Playbook – A CISO-Aligned Framework for Closing Enterprise Deals
The Cyber Sales Playbook – A CISO-Aligned Framework for Closing Enterprise Deals
The Cyber Sales Playbook – A CISO-Aligned Framework for Closing Enterprise Deals
Pipelines stall when seller motion conflicts with CISO decision logic. This playbook exposes the structural causes and provides solutions.
CISO decisions are driven by risk pressure, internal alignment, and budget windows. Any motion outside those constraints loses velocity.
Start with Module #1 – Early Qualification: Establishing Deal Viability
Playbook Architecture
11 modules. Each addresses a structural failure point in enterprise cyber sales. Each module is independent.
Modules are sequenced based on buyer decision architecture. Each module should be executed once all prior modules are completed. This avoids diagnostic noise from problems in earlier pipeline stages.
Each module includes diagnostics and corrective actions.
Stage 1: Viability
Stage 1: Viability
Early Qualification: Establishing Deal Viability
Early Qualification: Establishing Deal Viability
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Lead Targeting: Identifying Roles With Conversion Potential
Lead Targeting: Identifying Roles With Conversion Potential
Stage 2: Momentum
Stage 2: Momentum
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Messaging Architecture for Risk Owners
Messaging Architecture for Risk Owners
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Demo Structure: Maintaining Post-Call Momentum
Demo Structure: Maintaining Post-Call Momentum
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Evidence Sequencing Aligned to Buyer Decisions
Evidence Sequencing Aligned to Buyer Decisions
Stage 3: Decision
Stage 3: Decision
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Stakeholder Mapping and Influence Paths
Stakeholder Mapping and Influence Paths
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Procurement Flow: Budget Controls and Approval Gates
Procurement Flow: Budget Controls and Approval Gates
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Negotiation Patterns and Margin Protection
Negotiation Patterns and Margin Protection
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Objection Handling Across Late-Stage Risk Points
Objection Handling Across Late-Stage Risk Points
Stage 4: Expansion
Stage 4: Expansion
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Post-Close Adoption and Expansion Mechanics
Post-Close Adoption and Expansion Mechanics
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
UNDER CONSTRUCTION.
Measurement Framework for Continuous Improvement
Measurement Framework for Continuous Improvement
The Full Playbook
Modules are sequenced in dependency order.
Stage 1: Viability
2
Lead Targeting: Identifying Roles With Conversion Potential
MODULE UNDER CONSTRUCTION.
Lead targeting quality determines outbound efficiency.
Module #2 improves lead quality by defining role targets and filtering early signals.
2
Lead Targeting: Identifying Roles With Conversion Potential
MODULE UNDER CONSTRUCTION.
Lead targeting quality determines outbound efficiency.
Module #2 improves lead quality by defining role targets and filtering early signals.
Stage 2: Momentum
3
Messaging Architecture for Risk Owners
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
Messaging determines whether risk owners respond with specificity.
Module #3 ensures messaging matches risk owner priorities and regulatory pressures.
3
Messaging Architecture for Risk Owners
MODULE UNDER CONSTRUCTION.
Messaging determines whether risk owners respond with specificity.
Module #3 ensures messaging matches risk owner priorities and regulatory pressures.
4
Demo Structure: Maintaining Post-Call Momentum
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
Demo structure determines post-demo momentum.
Module #4 examines demo structure to prevent loss of post-call momentum.
4
Demo Structure: Maintaining Post-Call Momentum
MODULE UNDER CONSTRUCTION.
Demo structure determines post-demo momentum.
Module #4 examines demo structure to prevent loss of post-call momentum.
5
Evidence Sequencing Aligned to Buyer Decisions
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
Evidence sequencing determines whether buyers internalize your value or defer judgment.
Module #5 orders evidence to align with buyer decision sequence.
5
Evidence Sequencing Aligned to Buyer Decisions
MODULE UNDER CONSTRUCTION.
Evidence sequencing determines whether buyers internalize your value or defer judgment.
Module #5 orders evidence to align with buyer decision sequence.
Stage 3: Decision
6
Stakeholder Mapping and Influence Paths
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
Stakeholder mapping determines whether hidden veto players derail the deal.
Module #6 maps stakeholder roles and identifies veto points.
6
Stakeholder Mapping and Influence Paths
MODULE UNDER CONSTRUCTION.
Stakeholder mapping determines whether hidden veto players derail the deal.
Module #6 maps stakeholder roles and identifies veto points.
7
Procurement Flow: Budget Controls and Approval Gates
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
Procurement navigation determines whether budget controls stall progress.
Module #7 clarifies procurement sequence and budget controls.
7
Procurement Flow: Budget Controls and Approval Gates
MODULE UNDER CONSTRUCTION.
Procurement navigation determines whether budget controls stall progress.
Module #7 clarifies procurement sequence and budget controls.
8
Negotiation Patterns and Margin Protection
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
Negotiation patterns determine whether margin erosion accelerates under pressure.
Module #8 identifies negotiation patterns and margin pressures.
8
Negotiation Patterns and Margin Protection
MODULE UNDER CONSTRUCTION.
Negotiation patterns determine whether margin erosion accelerates under pressure.
Module #8 identifies negotiation patterns and margin pressures.
9
Objection Handling Across Late-Stage Risk Points
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
Objection handling determines whether late-stage doubt converts into delay or closure.
Module #9 prepares for typical late-stage objections.
9
Objection Handling Across Late-Stage Risk Points
MODULE UNDER CONSTRUCTION.
Objection handling determines whether late-stage doubt converts into delay or closure.
Module #9 prepares for typical late-stage objections.
Stage 4: Expansion
10
Post-Close Adoption and Expansion Mechanics
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
Post-close execution determines retention and expansion probability.
Module #10 defines post-close steps to ensure adoption.
10
Post-Close Adoption and Expansion Mechanics
MODULE UNDER CONSTRUCTION.
Post-close execution determines retention and expansion probability.
Module #10 defines post-close steps to ensure adoption.
11
Measurement Framework for Continuous Improvement
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
MODULE UNDER CONSTRUCTION.
Measurement discipline determines whether the sales motion improves or repeats failure loops.
Module #11 defines key metrics for ongoing improvement.
11
Measurement Framework for Continuous Improvement
MODULE UNDER CONSTRUCTION.
Measurement discipline determines whether the sales motion improves or repeats failure loops.
Module #11 defines key metrics for ongoing improvement.
More coming?
Yes. Get notified when a new playbook module or tool is published – no newsletters, no promotions.
Design Principles
Built around CISO decision logic.
Diagnostics precede tactics.
Corrective actions verify themselves within weeks through lightweight CRM fields or simple reports.
Modules operate independently and without dependence on proprietary tools.
FAQ
How long to implement the full playbook?
How long to implement the full playbook?
How long to implement the full playbook?
How long to implement the full playbook?
Is this for enterprise vendors?
Is this for enterprise vendors?
Is this for enterprise vendors?
Is this for enterprise vendors?
Is this for startups / scale-ups?
Is this for startups / scale-ups?
Is this for startups / scale-ups?
Is this for startups / scale-ups?
What if my team resists?
What if my team resists?
What if my team resists?
What if my team resists?
Ready to win more deals?
See immediate clarity with a live deal this week.

CISO-Aligned Deal Advisory
by Michal Sobiegraj
Former long-time enterprise cyber security executive. I help cyber security sales directors win enterprise deals applying my firsthand knowledge of what moves deals forward – and what doesn’t.
Legal stuff
© 2025 Michal Sobiegraj. All rights reserved
Ready to win more deals?
See immediate clarity with a live deal this week.

CISO-Aligned Deal Advisory
by Michal Sobiegraj
Former long-time enterprise cyber security executive. I help cyber security sales directors win enterprise deals applying my firsthand knowledge of what moves deals forward – and what doesn’t.
Legal stuff
© 2025 Michal Sobiegraj. All rights reserved
Ready to win more deals?
See immediate clarity with a live deal this week.

CISO-Aligned Deal Advisory
by Michal Sobiegraj
Former long-time enterprise cyber security executive. I help cyber security sales directors win enterprise deals applying my firsthand knowledge of what moves deals forward – and what doesn’t.
Legal stuff
© 2025 Michal Sobiegraj. All rights reserved