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Implementation Plan

18-month phased rollout with parallel running, pilot groups, and clear rollback criteria

📊 Success Metrics

50%
Vendor Spend Reduction
2.5h
Daily Time Saved Per Rep
0%
Productivity Disruption
18mo
Full Implementation

📅 Gantt Overview

Workstream
M1
M2
M3
M4
M5
M6
M7
M8
M9
M10
M11
M12
M13
M14
M15
M16
M17
M18
R2 Migration (S3)
R2
Workspace Agents
Automations
Internal APIs
Workers + D1
AI Meeting Summaries
Workers AI
Content Search
Vectorize + RAG
Workflow Engine
CF Workflows
Deal Risk Scoring
ML Models
AI Agents
Agents SDK

🚀 Phase 1: Quick Wins (Months 1-6)

Low-Risk, High-Impact Consolidations
Months 1-6
Week 1-2
Project Kickoff & Infrastructure Setup
Establish Cloudflare Workers environment, CI/CD pipelines, and development standards.
Wrangler Config GitHub Actions Dev Standards Doc
Platform Team
Week 3-6
R2 Migration (Replace S3)
Migrate file storage from S3 to R2. Zero egress fees = immediate cost savings.
R2 Buckets Migration Scripts $50K+ Savings
Data Eng
Week 4-10
Workspace Studio Agents (Replace Zapier)
Build no-code automation agents for common workflows: email triage, status reports, reminders.
10 Agents User Training Zapier Sunset
RevOps
Week 8-24
Internal APIs on Workers + D1
Migrate internal API endpoints from legacy infrastructure to Workers. Use D1 for data persistence.
5 APIs Migrated D1 Schemas API Docs
Backend Team

⚡ Phase 2: Core Infrastructure (Months 7-12)

Strategic Platform Builds
Months 7-12
Week 25-36
AI Meeting Summaries (Partial Gong Replace)
Build transcription + summarization pipeline using Workers AI (Whisper) + Gemini API.
Whisper Integration Gemini Summaries SFDC Sync 10% Pilot
AI Team
Week 28-42
Sales Content Search (Partial HighSpot Replace)
Build semantic search using Vectorize + Workers AI embeddings. RAG pipeline with Gemini.
Vectorize Index Search UI Content Ingestion
AI Team
Week 32-48
Workflow Engine (Replace Workato)
Build durable workflow orchestration using Cloudflare Workflows. Migrate complex automations.
Workflow Templates Monitoring Workato Sunset
Platform Team

🤖 Phase 3: Advanced Capabilities (Months 13-18)

AI-Powered GTM Transformation
Months 13-18
Week 49-60
Deal Risk Scoring
Build predictive deal health using Workers AI classification + historical pattern matching.
ML Model SFDC Integration Risk Dashboard
AI Team
Week 52-72
AI Agents (Agents SDK + Opencode MCP)
Build autonomous agents for account research, competitive intel, and deal preparation.
Agent Framework MCP Tools 3 Production Agents
AI Team
Week 68-72
Full Rollout & Vendor Sunset
Complete migration from external vendors. Final training and documentation.
100% Adoption Vendor Contracts Ended 50% Savings Achieved
All Teams

🛡️ Risk Mitigation

Risk Likelihood Impact Mitigation
Sales productivity drops during transition Medium High Parallel running for 30-60 days; automatic rollback if productivity drops >5%
Internal build takes longer than expected Medium Medium Phased approach allows re-prioritization; vendor contracts extended if needed
AI quality doesn't match vendor tools Low Medium 10% pilot groups validate quality before rollout; hybrid approach if needed
Team lacks Cloudflare expertise Medium Low Training program in Phase 1; Cloudflare professional services available
Data migration issues Low Medium Comprehensive testing; D1 Time Travel for recovery; staged migrations

👥 Team Structure

🏗️

Platform Team

Owns Cloudflare infrastructure and core services.

  • 2 Senior Engineers
  • 1 DevOps Engineer
  • Workers, D1, R2, Workflows
  • CI/CD and monitoring
🤖

AI Team

Owns AI/ML features and integrations.

  • 2 ML Engineers
  • 1 AI Product Manager
  • Workers AI, Gemini, Vectorize
  • Opencode + MCP development
⚙️

RevOps Team

Owns business logic and user adoption.

  • 2 RevOps Analysts
  • 1 Enablement Lead
  • Workspace Studio agents
  • Training and documentation
🔗

Integration Team

Owns external system connections.

  • 2 Integration Engineers
  • Salesforce, Gong, Calendar APIs
  • Data sync and validation
  • Hyperdrive connections

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