Multi-Turn Conversational Simulations

Your CEO Doesn't Click on Free Pizza Links.
They Click on Board Meeting Minutes.

Test decision-making, not just click reflexes.

Legacy platforms send single-email templates that employees learn to spot. ThinSky deploys professionally relevant simulations that mirror real business correspondence - exactly how real threat actors compromise high-value targets.

$3,000
Bespoke Setup
Multi-Turn
Conversations
Zero
Admin Overhead
See Multi-Turn in Action See Pricing Model
SOC 2 Aligned
GDPR Compliant
ISO 27001 Ready
Segregated Cloud LLM

Why Single-Email Phishing Tests Leave Gaps

Why do high-value targets fail consistently at spotting phishing attempts but pass in training? Traditional simulations use obvious templates. Real attackers engage in back-and-forth conversations, building trust over multiple exchanges.

Template Memorization

Employees learn to recognize your phishing tests, not real threats. Generic templates create pattern recognition, not critical thinking.

Single-Click Metrics

Measuring "did they click?" doesn't reveal how employees reason under pressure. Real compromises happen after sustained engagement.

Context Failure

Sending "Package Delivery" alerts to finance teams who handle wire transfers tests nothing. Role context matters.

The Two-Tier Managed Strategy

ThinSky is a "Done-For-You" managed service. Our analysts explore your organization's publicly accessible information, compiling facts and notable details to ensure every simulation is professionally relevant to the targets.

Tier 1 The Spear

Multi-Turn Conversations for High-Value Targets

Finance controllers, IT administrators, HR personnel, and key decision-makers.

For your High-Value Targets (HVTs), we can deploy adaptive multi-turn conversations that unfold over days - when the scenario warrants it.

  • Sustained engagement: Multi-turn conversations that build credibility before introducing risk.
  • OSINT-powered: Scenarios based on actual vendors, partners, and systems your team uses.
  • Behavioral insights: Learn exactly when and why targets trust a malicious actor.
Tier 2 The Net

Tactical Simulations for the Organization

Deployed for the general workforce.

For the broader organization, we utilize high-fidelity, volume-based simulations.

  • Broader organizational context (e.g., "Open Enrollment" or "IT Policy Updates").
  • Test adherence at scale without individual operational overhead.
  • High-fidelity simulations that scale efficiently across departments.

Decelerating Scale Pricing

Front-Loaded Bespoke, Controlled Scale. Resets Monthly.

Our pricing model is designed to incentivize quality over quantity. The cost per target decreases as you scale, ensuring you can test your high-value targets affordably while maintaining a premium floor for our analyst-led service.

1 Phase 1: The Foundation (One-Time Fee)

Service Cost Deliverable
Deep Reconnaissance $1,500 Analysts map roles, vendors, and public data to build relevant contexts.
Deployment & Config $1,500 Custom infrastructure setup ensuring 100% deliverability.
Total Setup $3,000 One-time fee to establish your threat environment and create a creative strategy ongoing through the life of the engagement.

2 Phase 2: The Campaign ("Decelerating Cost" Execution)

Each unique campaign targets a specific group with professionally crafted, reconnaissance-based content. Multi-turn conversations are executed where appropriate.

FIRST CAMPAIGN
$600.00
1st Campaign
  • Department or group-specific content
  • Multi-turn option available
ADDITIONAL CAMPAIGNS
Same Month
2nd Campaign $400.00
All Remaining Campaigns $250.00 (Floor)

The Value: Every campaign is highly relevant, professionally crafted based on reconnaissance. Small intentional tells reward the most attentive employees.

Example Month: 8 Campaigns

Each campaign targets a specific group with unique, relevant content:

# Campaign Target Cost
1 Finance Department — could be multi-turn $600
2 IT Team — could be multi-turn $400
3 All Staff $250
4 Sales Department — could be multi-turn $250
5 Remaining Staff $250
6 Accounts Payable — could be multi-turn $250
7 Front Desk Staff $250
8 HR Department — could be multi-turn $250
Monthly Total $2,500

*One-time $3,000 setup fee applies. All campaigns include reconnaissance-based content crafted by our analysts.

Want to see examples of real past campaigns?

We'd be happy to walk you through what we've done for similar organizations.

Schedule a Call

The Hidden Cost of Template-Based Training

See how multi-turn conversational simulations compare to legacy vendors.

Metric Template-Based (KnowBe4/Proofpoint) ThinSky Multi-Turn
Methodology Single email: Click or don't click Multi-turn: Adaptive conversational simulations
What It Tests Click reflexes: Pattern recognition Decision-making: Critical thinking under pressure
Behavioral Insight Binary: Clicked / Didn't Click Nuanced: Where and why trust was established
Your Effort High (You must select and filter templates) Zero (Analyst-led, fully managed)

Live Webinar Training for Failed Simulations

When individuals fail a simulation, we don't serve them two hours of videos with testing in order to check a box. We hold live 15-minute training sessions that are relevant, engaging, and designed to change behavior.

  • Multiple sessions daily: Employees select a time that suits them best
  • Only 15 minutes: Not two hours of videos - just focused, relevant training
  • Webinar format: Employees don't see each other - private, non-judgmental environment
  • Conducted by security analysts: Real experts, not canned content

The Risk of Generic Templates

  • False confidence: High pass rates on simple tests don't reflect readiness for sophisticated attacks
  • Pattern recognition: Employees spot familiar templates but miss novel threats
  • Compliance theater: You meet requirements without actually reducing breach risk

Train Against Relevance, Not Just Emails.

Where we use templates, they are constructed purposefully for your targets and are extremely relevant.

See Multi-Turn in Action

Phase 1 Reconnaissance: $3,000 | Then deploy multi-turn simulations.