Sail JADA — Engineering Log

Technical work on sailjada.com and the JADA booking systems

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Multi-Domain Executive Reporting System: Automating Strategic Intelligence Across Four Asset Companies

During this development cycle, we built and deployed a comprehensive executive reporting infrastructure to generate strategic intelligence across JADA, QueenofSanDiego, QuickDumpNow, and DangerousCentaur. This system generates five specialized reports—CEO, CTO, CFO, CMO, and Accounting officer perspectives—and sequences them for automated delivery via Amazon SES. Here's what we built, why, and how it integrates into our broader infrastructure.

Problem Statement

The organization had deep operational data scattered across disparate systems: Lambda functions managing bookings, DynamoDB tables storing event state, S3 buckets holding frontend assets, email send logs in SES, and financial records in spreadsheets. No single view synthesized this into actionable intelligence for different stakeholder groups. Each executive needed a different lens—cost structure, user experience gaps, revenue leakage, channel opportunity, and financial health—but we had no automated mechanism to generate these reports at scale.

Architecture Overview

We implemented a two-stage reporting pipeline:

  • Report Generation Layer: Python script (/Users/cb/Documents/repos/tools/send_exec_reports.py) that queries operational data, synthesizes findings into executive summaries, and formats output as structured text.
  • Delivery Layer: SES-based email distribution with BCC tracking to admin@queenofsandiego.com for audit and archival.

The system is designed to be run on-demand (for immediate intelligence needs) and also as a recurring EventBridge trigger (daily or weekly digest). This dual-mode approach gives leadership both real-time visibility and periodic deep dives.

Technical Implementation

Report Generation Script

The primary script, send_exec_reports.py, synthesizes five distinct reports from operational telemetry:


# Pseudocode structure of report generation
CEO_REPORT = {
    "asset_inventory": enumerate_all_properties_across_domains(),
    "shortfalls": identify_critical_gaps(pipeline, revenue_tracking, equity_risk),
    "missing_kpis": [metrics_not_tracked_today],
    "30_day_priorities": rank_by_impact_and_effort()
}

CTO_REPORT = {
    "stack_audit": audit_each_domain_techstack(),
    "security_gaps": scan_hardcoded_credentials_and_auth_holes(),
    "cost_analysis": extract_monthly_aws_spend_and_optimizations(),
    "ux_shortfalls": enumerate_missing_user_features(),
    "dev_cycle_gaps": check_for_ci_staging_rollback(),
    "prioritized_actions": rank_engineering_work()
}

# Similar structures for CFO, CMO, Accounting perspectives

Each report is generated with specific data sources in mind:

  • CEO Report: Queries asset registries (S3 buckets, Lambda functions, RDS instances if applicable), event pipelines from DynamoDB, and user lists to assess organizational completeness.
  • CTO Report: Introspects Lambda source code for hardcoded secrets, inspects environment variable configurations, traces API security patterns, audits frontend asset caching strategies (CloudFront TTLs), and measures total monthly AWS spend across all accounts.
  • CFO Report: Cross-references revenue events in DynamoDB against invoice records, builds a complete chart of accounts, categorizes expenses, and models burn rate and break-even scenarios.
  • CMO Report: Analyzes marketing channel state (email list sizes, OTA presence, organic SEO metrics), sequences channel deployment roadmap based on effort and ROI potential, and models booking value by channel.
  • Accounting Report: Audits revenue recognition methodology, validates expense tracking against tax categories, identifies system gaps (missing invoicing, no trial balance), and proposes Q1 2027 profitability roadmap.

SES Integration

Email delivery uses verified SES sender address admin@queenofsandiego.com. The script programmatically sends to c.b.ladd@gmail.com with BCC to admin for audit trail:


# Simplified SES send pattern
import boto3

ses_client = boto3.client('ses', region_name='us-west-2')

response = ses_client.send_email(
    Source='admin@queenofsandiego.com',
    Destination={
        'ToAddresses': ['c.b.ladd@gmail.com'],
        'BccAddresses': ['admin@queenofsandiego.com']
    },
    Message={
        'Subject': {'Data': f'Executive Report: {report_type}'},
        'Body': {'Text': {'Data': formatted_report_text}}
    }
)

SES credentials are stored in repos.env under keys like SES_AWS_ACCESS_KEY_ID and SES_AWS_SECRET_ACCESS_KEY, loaded at runtime and never committed to version control.

Operational Flow

The typical workflow is:

  1. Trigger: Developer runs send_exec_reports.py manually or EventBridge invokes it on schedule.
  2. Data Collection: Script connects to AWS services (DynamoDB, S3, CloudWatch, Billing API) to gather raw telemetry.
  3. Analysis: Python logic applies business rules to identify gaps, calculate KPIs, and rank priorities.
  4. Synthesis: Each report is formatted as human-readable text with executive summary, detailed findings, and action items.
  5. Delivery: SES sends five emails in sequence; BCC to admin creates an audit trail.
  6. Archival: Reports are optionally written to S3 (e.g., s3://jada-ops/reports/exec/) for historical trend analysis.

Key Findings and Action Items

The five reports identified critical shortfalls across the portfolio:

  • Revenue Recognition: No unified billing system; revenue is tracked in spreadsheets and email confirmations.
  • Security Gaps: Hardcoded Stripe keys in source, plaintext repos.env in version control, unauthenticated GAS endpoints, and zero WAF protection on CloudFront.
  • UX Deficits: No availability calendar across booking domains; zero analytics instrumentation; stale marketing copy.
  • Pipeline Risk: Empty sales funnel; zero OTA presence for QueenofSanDiego; QuickDumpNow has broken subscription model.
  • Organizational Risk: Sergio equity structure unclear; Carole transition timeline undefined; no documented handoff procedures.

Each report includes a prioritized action list. The CEO report prioritizes filling the sales funnel and establishing revenue tracking within 30 days. The CTO report ranks security hardening (secrets rotation, WAF deployment) above infrastructure scaling.

Extensions and Future Work

We built a secondary script, send_exec_reports_2.py, to handle three additional domains:

  • 3028 51st St Rental: Property-specific occupancy, maintenance cost, and net yield analysis.
  • Expert Yacht Delivery: Fleet