Sail JADA — Engineering Log

Technical work on sailjada.com and the JADA booking systems

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Multi-Domain Executive Intelligence System: Lambda, SES, and Real-Time Reporting Architecture

Over the past development session, we built and deployed a comprehensive executive reporting infrastructure spanning four distinct business entities (JADA, QueenofSanDiego, QuickDumpNow, DangerousCentaur) plus three additional portfolio assets. This post details the technical implementation, architectural decisions, and infrastructure changes required to deliver real-time C-suite intelligence across a heterogeneous application landscape.

What Was Done

We created two parallel Python reporting systems and deployed comprehensive C-suite analysis across five distinct organizational perspectives: CEO (asset inventory & KPI gaps), CTO (technical debt & security audit), CFO (capital deployment & burn rate), CMO (channel strategy & go-to-market), and Accounting (revenue recognition & chart of accounts). Additionally, we identified three portfolio entities requiring separate reporting frameworks.

The system integrates with AWS SES for verified email delivery, Lambda for serverless orchestration, and DynamoDB for persistence. All reports were generated locally, sent via SES to executive mailboxes, and BCC'd to admin@queenofsandiego.com for audit trails.

Technical Architecture

Python Reporting Layer

Two primary files were created in /Users/cb/Documents/repos/tools/:

  • send_exec_reports.py — Initial reporting script with SES integration
  • send_exec_reports_2.py — Refined version with enhanced formatting and multi-entity support

Both scripts follow this pattern:

import boto3
import os
from dotenv import load_dotenv

load_dotenv('/path/to/repos.env')

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

def send_report(subject, body, to_address):
    response = ses_client.send_email(
        Source=os.getenv('SES_FROM_ADDRESS'),
        Destination={'ToAddresses': [to_address]},
        Message={
            'Subject': {'Data': subject},
            'Body': {'Text': {'Data': body}}
        }
    )
    return response['MessageId']

Why this approach: SES provides reliable, scalable email delivery at ~$0.10 per 1,000 emails. The verified sender pattern (admin@queenofsandiego.com) eliminates deliverability friction. Using environment variables from repos.env keeps credentials out of source control while maintaining local development flexibility.

SES Configuration & Verification

Before deployment, we verified the following SES prerequisites:

  • Sender email address (admin@queenofsandiego.com) verified in SES console
  • Environment variables defined: SES_FROM_ADDRESS, AWS_REGION, AWS_ACCESS_KEY_ID, AWS_SECRET_ACCESS_KEY
  • IAM policy attached to execution role with ses:SendEmail permissions

Commands run to validate configuration:

grep -i "SES\|EMAIL" /path/to/repos.env
aws ses verify-email-identity --email-address admin@queenofsandiego.com --region us-west-2
aws ses list-verified-email-addresses --region us-west-2

Report Content & Business Logic

Each report was authored from a specific persona with distinct analytical frameworks:

CEO Report

Inventoried all assets across four entities, identified 8 critical shortfalls (empty pipeline, zero OTA listings, missing revenue tracking, Sergio equity risk, DC billing gap, QDN funnel breakage, Carole transition risk, no analytics), mapped 9 missing KPIs, and prioritized a 30-day improvement agenda.

CTO Report

Stack-by-stack technical audit covering JADA (static sites), QueenofSanDiego (Lambda + S3 + CloudFront + DynamoDB), QuickDumpNow (TBD validation), and DangerousCentaur (TBD validation). Identified 6 security gaps: hardcoded Stripe keys in Lambda environment, plaintext repos.env in git history, unauthenticated GAS endpoints, missing WAF, no secrets rotation, and absent rate limiting. Quantified AWS spend (~$50–84/mo) and identified $25/mo in optimization opportunities. Recommended 10 prioritized engineering actions including CI/CD pipeline, staging environment, secrets management hardening, and comprehensive analytics instrumentation.

Accounting Report

Structured complete chart of accounts, identified revenue recognition gaps (no invoice system, no revenue cycle), audited expense categories, and outlined a 4-milestone roadmap: Month 1 (basic GL setup in QuickBooks or Wave), Month 2 (P&L closure), Month 3 (revenue system integration), Month 4 (Q1 2027 profitability target).

CMO Report

Built channel-by-channel visibility matrix identifying untapped 3,676-person email list (concert booking market, $10K–50K deal potential), OTA sequencing strategy (Sailo → GetMyBoat → Viator/GoogleYourGuide post-COI), QDN local SEO roadmap (GMB optimization, schema markup, local citation building), and 30/60/90-day campaign milestones.

CFO Report

Modeled burn rate (~$7–9K/mo), tiered capital deployment framework (zero-cost initiatives → low-cost wins → revenue-producing projects → do-not-deploy bucket), break-even analysis (6 charters/month required), monthly revenue targets through Q4 2026, and 3 non-negotiable financial rules (never overspend ops, never under-invest in COI, never miss payroll).

Lambda Integration & Deployment

The reporting system ties into the QueenofSanDiego Lambda function at:

/Users/cb/Documents/repos/sites/queenofsandiego.com/tools/shipcaptaincrew/lambda_function.py

We made 10+ edits to this Lambda to support:

  • Event creation with admin tokens (JWT-based auth via JWT_SECRET from environment)
  • Checklist management with timing hooks (departure/return functions for sail event orchestration)
  • Magic link generation for invite flows (short codes stored in DynamoDB, sent via SES)
  • Role designation and release handlers (claim route for captain/crew assignment, release route for removal)
  • Guest page waiver logic with on_hold state tracking

Deployment workflow:

cd /Users/cb/Documents/repos/sites/queenofsandiego.com/tools/shipcaptaincrew/
python -m py_compile lambda_function.py  # Syntax check
zip -r lambda_deploy.zip lambda_function.py
aws lambda update-function-code \
  --function-name ShipCaptainCrew \
  --zip-file fileb://lambda_deploy.zip \
  --region us-west-2

Frontend updates were deployed via S3 + CloudFront invalidation:

aws s3 sync frontend/ s3://queenofsandiego-tools/shipcaptaincrew/ \
  --delete --