Queen of San Diego — Tech Blog

Under the hood at queenofsandiego.com

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Multi-Perspective Executive Reporting Infrastructure: Automated SES Deployment of Strategic Analysis Across the Portfolio

Over a two-week development sprint focused on the ShipCaptainCrew Lambda function and related tooling, we identified a critical gap: no systematic way to deliver comprehensive strategic analysis to stakeholders across different functional domains. This post details how we built an automated executive reporting pipeline that generates and distributes eight distinct analytical reports—each tailored to a specific role and perspective—using AWS SES, DynamoDB, and Python-based report generation.

What Was Done

We created two parallel report generation systems to serve different stakeholder constituencies:

  • Initial five-report system (/Users/cb/Documents/repos/tools/send_exec_reports.py): CEO, CTO, Accounting Officer, CMO, and CFO perspectives on the four core entities (JADA, QueenofSanDiego, QuickDumpNow, DangerousCentaur).
  • Extended portfolio system (/Users/cb/Documents/repos/tools/send_exec_reports_2.py): Three additional specialized reports covering 3028 51st St Rental operations, Expert Yacht Delivery infrastructure, and DangerousCentaur client billing audits.
  • Destination inbox: All reports delivered to c.b.ladd@gmail.com with BCC to admin@queenofsandiego.com (verified SES sender domain).

Each report is role-specific and asset-aware. For example, the CTO report audits every tech stack in the portfolio (JADA's Django/PostgreSQL, QueenofSanDiego's Lambda/S3/CloudFront, QuickDumpNow's web presence, DangerousCentaur's client portal), while the CEO report focuses on revenue leakage, asset utilization, and 30-day execution priorities.

Technical Details: Report Architecture

Report Generation Method

Each report is generated as a multi-paragraph analysis with structured sections:


# CEO Report structure
- Full asset inventory (domain registrars, S3 buckets, Lambda functions, DynamoDB tables)
- 8–10 critical shortfalls (empty sales pipeline, no revenue tracking system, Sergio equity risk, zero OTA listings)
- 9+ missing KPIs (charter utilization rate, cost-per-booking, customer acquisition cost, churn rate)
- 30-day prioritized action agenda

CTO Report structure


- Stack-by-stack audit:
  * JADA: Django, PostgreSQL, Gunicorn, static hosting (audit: auth hardening, DB backups)
  * QueenofSanDiego: Lambda (shipcaptaincrew), S3 (frontend), CloudFront (CDN), Route53 (DNS), DynamoDB (events/checklists/users)
  * QuickDumpNow: web presence audit
  * DangerousCentaur: client portal stack
- 6 security gaps (hardcoded Stripe keys in repos, plaintext repos.env in version control, unauthenticated GAS endpoints, no WAF)
- AWS cost analysis (~$50–84/mo current spend, ~$25/mo in easy savings)
- UX shortfalls (no availability calendar, zero analytics, stale copy)
- Dev cycle audit (no CI/CD, no staging environment, no rollback strategy)
- 10 prioritized engineering actions

Accounting Officer Report structure


- Revenue recognition audit (what we think we're earning vs. what we're actually tracking)
- Chart of accounts completeness check
- Expense audit by category
- Identified gap: zero accounting system currently in place
- 4-milestone roadmap to profitability through Q1 2027

CMO Report structure


- Channel-by-channel visibility matrix (email, OTA, organic search, partnerships)
- ROI case for 3,676-person email blast ($10K–50K potential concert/charter bookings)
- OTA deployment sequence: Sailo (first), GetMyBoat (second), Viator/GYG/Airbnb (after COI achieved)
- QuickDumpNow local SEO roadmap
- 30/60/90-day campaign milestones

CFO Report structure


- Monthly burn rate model (~$7–9K/mo across all entities)
- Tiered capital deployment framework:
  * Tier 1: Zero-cost improvements (security, process, communications)
  * Tier 2: Low-cost (under $500: tools, scripts, monitoring)
  * Tier 3: Revenue-producing (charter bookings, SaaS products, rentals)
  * Tier 4: Do not deploy here (speculative tech, vanity projects)
- Break-even analysis: 6 charters/month on QueenofSanDiego
- Monthly revenue targets through Q4 2026
- Three non-negotiable financial rules

Infrastructure and Deployment

SES Configuration

All reports are sent via AWS SES from the verified sender admin@queenofsandiego.com. This avoids the complexity of configurable sender addresses while maintaining audit trail through the BCC field. The SES API call is straightforward:


# Pseudo-code structure
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'[{role}] Executive Report – Portfolio Analysis'},
        'Body': {'Text': {'Data': report_text}}
    }
)

Data Sources

Report data is drawn from:

  • repos.env: SES configuration variables (sender address, region)
  • Agent handoff documents (/Users/cb/Documents/repos/agent_handoffs/projects/*.md): Project scope, asset inventory, known gaps
  • Live CloudFormation/AWS console queries: S3 buckets, Lambda functions, DynamoDB tables, Route53 zones
  • Source code inspection: Stack audit by reading actual config files, security posture by analyzing source for hardcoded secrets
  • Historical command logs: Deployment history, cost patterns, infrastructure decisions

Key Decisions

Why Eight Reports Instead of One?

A single "executive summary" report would obscure the real value here: different stakeholders have completely different information needs and decision authorities. A CEO cares about revenue and asset utilization; a CTO cares about security, cost optimization, and user experience. By generating role-specific reports, each stakeholder receives exactly the analysis they need to make decisions in their domain.

Why BCC to admin@queenofsandiego.com?

This provides an audit trail without requiring a separate archiving system. Every report is logged in the company inbox, but delivery goes to the primary stakeholder (c.b.ladd@gmail.com). If we needed to trace when reports were generated, the SES receipt rules and SNS notifications could log