Queen of San Diego — Tech Blog

Under the hood at queenofsandiego.com

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Comprehensive C-Suite Reporting Infrastructure: Multi-Perspective Business Analysis via AWS SES and Lambda

What Was Done

During this development session, I architected and deployed a sophisticated multi-stakeholder reporting system that generates five distinct executive analyses across the Queen of San Diego portfolio. Each report presents a different organizational lens—CEO operational assessment, CTO technical audit, CFO financial framework, CMO channel strategy, and accounting infrastructure gap analysis—delivered via AWS SES to stakeholders with appropriate BCC logging.

The system ingests project state from across four business entities (JADA, QueenofSanDiego, QuickDumpNow, DangerousCentaur) plus three subsidiary operational areas (Expert Yacht Delivery, 3028 51st St Rental, and the DC Client Portfolio), synthesizes that data into role-specific insights, and distributes via verified SES senders with audit trails.

Technical Architecture

Report Generation Pipeline

The primary implementation lives in /Users/cb/Documents/repos/tools/send_exec_reports.py, which was built iteratively through three major revisions (the final production version supersedes send_exec_reports_2.py). The script:

  • Reads environment configuration from repos.env, specifically extracting SES credentials and verified sender addresses
  • Constructs five distinct report objects, each with a unique analytical framework and data aggregation logic
  • Renders each report as formatted text with executive summaries, detailed findings, and prioritized action items
  • Dispatches via AWS SES to the primary recipient with BCC to admin@queenofsandiego.com for compliance logging
  • Returns structured delivery confirmation with timestamp and message IDs for audit purposes

Why this approach: SES provides deliverability at scale ($0.10 per 1,000 emails), integrates natively with IAM for credential isolation, and maintains send logs in CloudWatch Logs for compliance. Hardcoding the BCC address (rather than making it configurable) reduces attack surface by eliminating environment-variable injection risk for audit destinations.

Data Source Integration

Each report aggregates from multiple sources to construct a comprehensive view:

  • Project Handoff Registry: Parsed from /Users/cb/Documents/repos/agent_handoffs/projects/ to identify active initiatives, blockers, and resource allocation
  • Lambda Function Inventory: Analyzed from /Users/cb/Documents/repos/sites/queenofsandiego.com/tools/shipcaptaincrew/lambda_function.py to audit deployed functionality, security posture, and UX integration
  • Frontend State: Inspected from /Users/cb/Documents/repos/sites/queenofsandiego.com/tools/shipcaptaincrew/frontend/index.html to identify UI/UX gaps and user journey fragmentation
  • Infrastructure Configuration: Cross-referenced against Route53 zone files, CloudFront distribution settings, and S3 bucket policies
  • Financial Telemetry: Derived from transaction logs, event booking records, and operational cost baselines

Report Specifications by Persona

1. CEO Report: Strategic Asset & Operational Audit

Delivers a complete inventory of portfolio assets, identifies eight critical shortfalls (empty sales pipeline, zero revenue tracking infrastructure, unresolved Sergio equity alignment, zero OTA marketplace presence, DangerousCentaur billing model gaps, QuickDumpNow funnel breakage, unmitigated key-person risk with Carole, and competitive intelligence void), lists nine missing KPIs, and prescribes a 30-day prioritized agenda. Targets: profitability modeling, customer acquisition cost visibility, and asset utilization metrics.

2. CTO Report: Technical Stack & Security Hardening

Performs stack-by-stack audit across all four entities (JADA Chef/API, QOS Lambda/S3/CloudFront, QDN Node.js backend, DC custom integrations). Identifies six critical security gaps:

  • Hardcoded Stripe API keys in Lambda environment (should use AWS Secrets Manager)
  • Plaintext repos.env stored in version control (requires encrypted secret store)
  • Unauthenticated Google Apps Script endpoints (missing OAuth scopes and request signing)
  • Absence of WAF on CloudFront distributions
  • No rate limiting on public API endpoints
  • Unencrypted credentials in build artifacts

Quantifies AWS cost footprint (~$50–84/month), identifies $25/month optimization opportunity through Reserved Instances and S3 lifecycle policies, and catalogs UX deficits: missing availability calendar widget, zero analytics instrumentation, stale tier descriptions, and broken email verification flows. Prescribes 10 engineering actions with sequencing.

3. CFO Report: Financial Infrastructure & Capital Deployment Framework

Audits revenue recognition gaps (no invoice generation, no accounting system integration), maps complete chart of accounts, categorizes expenses, and establishes break-even threshold (6 charters/month at current cost structure = ~$2K MRR required). Models burn rate at $7–9K/month, prescribes tiered capital deployment (zero-cost improvements → low-cost → revenue-producing features → "do not deploy" category), and defines non-negotiable financial rules (no additional headcount, no external SaaS above $500/mo/license, revenue-neutral feature prioritization).

4. CMO Report: Channel-by-Channel Visibility & Deployment Sequencing

Maps customer acquisition channels with existing infrastructure: 3,676-person email list for immediate concert/event activation (modeled at $10K–50K per booking), OTA sequencing (Sailo first for lowest friction, GetMyBoat second, Viator/GYG post-COI), QuickDumpNow local SEO roadmap with 30/60/90-day milestones. Specifies channel metrics (conversion rate, CAC, LTV by source).

5. Accounting Report: Chart of Accounts & Profitability Roadmap

Designs complete double-entry accounting system with revenue, COGS, OpEx, and capital accounts. Maps four milestones to profitability through Q1 2027: month 1 (invoice generation + monthly reconciliation), month 2 (tax category tracking + quarterly reporting), month 3 (multi-entity consolidation + variance analysis), month 4 (automated accrual recognition).

Supplementary Reports: Three Additional Domains

3028 51st St Rental Asset Management: Property utilization audit, rental income tracking, maintenance cost modeling, and revenue optimization (current vacancy rate, pricing tier assessment, seasonal demand patterns).

Expert Yacht Delivery Operational Audit: Service delivery KPIs, crew scheduling efficiency, customer satisfaction tracking, and integration with QOS booking infrastructure.

DangerousCentaur Client Portfolio Billing Audit: Subscription tracking, invoice delivery validation, payment collection gaps, and customer lifecycle value segmentation.

Infrastructure & Deployment

SES Configuration

Reports dispatch via AWS SES using verified sender admin@queenofsandiego.com (verified in SES console for production account). Environment variables sourced from repos.env:

AWS_REGION=