The Agentic AI
Transformation Playbook
A strategic guide for CPOs, CTOs, and PE Operating Partners navigating the shift from UI-first to agent-first architecture.
8 chapters covering the complete
transformation journey
The Agentic Imperative
Why this transformation is non-negotiable for mid-market SaaS. The mid-market advantage and what's at stake.
Read Chapter 1 →AI Readiness Assessment
5-dimension framework to assess your starting point. Score your organization and identify transformation priorities.
Available with Insider Annual or Advisory Circle
Architecture Patterns
4 proven patterns: Copilot Layer, Autonomous Workflows, Multi-Agent Orchestration, Agent-Native Platform.
Available with Insider Annual or Advisory Circle
Organizational Design
3-phase org model: AI Center of Excellence → Embedded AI Squads → AI-Native Organization.
Available with Insider Annual or Advisory Circle
Transformation Roadmap
4-phase implementation plan: Foundation → Pilot → Scale → Transform. 12-36 month timeline.
Available with Insider Annual or Advisory Circle
Measuring Success
3-tier KPI framework: Business Impact, AI Capability, Organizational Fluency. Board-ready metrics.
Available with Insider Annual or Advisory Circle
Common Pitfalls
6 failure modes and how to avoid them: Demo Trap, AI as Feature, Premature Scaling, and more.
Available with Insider Annual or Advisory Circle
PE Operating Partner Guidance
Due diligence framework, value creation milestones, investment sizing guidance.
Available with Insider Annual or Advisory Circle
Choose your level of access
Trusted by AI leaders at mid-market SaaS companies navigating the agentic shift.
Insider Monthly
$49/month
Content library, office hours recordings, and AI news. Playbook not included.
- ✓ Full content library access
- ✓ Office hours recordings
- ✓ Curated AI news & analysis
- ✓ Playbook Chapter 1 only
Insider Annual · Best Value
$499/year
Everything in monthly plus the complete 8-chapter playbook, released on a drip schedule.
- ✓ Everything in Insider Monthly
- ✓ Complete 8-chapter playbook
- ✓ Chapters 1-2 at signup
- ✓ New chapters every month
- ✓ Future updates included
Advisory Circle
$200/month
The complete experience: immediate full playbook access, live group calls, private Slack, and quarterly 1:1.
- ✓ Everything in Insider Annual
- ✓ Full playbook — immediate access
- ✓ Live monthly group calls
- ✓ Private Slack community
- ✓ Quarterly 1:1 with Jess
Consulting Clients
The complete playbook is also included with all consulting packages at no additional cost.
Strategy Session ($1,500) · Transformation Sprint ($7,500) · Fractional Retainer ($8,000/mo)