David Dittman
Executive technology and operations leadership
Writing

Articles

Perspectives on technology leadership, operations, marketing systems, and scaling businesses.

Engineering DevOps AI

Building a Zero-Cost Development Pipeline

Local-first AI coding agents, self-hosted runners, and quality gates that catch issues before they get expensive.

July 19, 2024
AI Customer Service Operations

Building an AI-First Customer Service Operation

How to implement tiered AI automation in customer service, from chatbots to AI agents to human escalation.

June 14, 2024
Marketing Analytics Data

The Attribution Problem Nobody Wants to Solve

Why last-click attribution persists, building a customer data platform, and practical approaches to incrementality testing.

May 19, 2024
Content Automation Publishing

Automating Content Publishing at Scale

Building headless publishing pipelines with AI-assisted content generation and human checkpoints.

April 9, 2024
Leadership Engineering Strategy

Leading a Technology Team Through Platform Migration

Why migrations fail and how to plan cutover, manage stakeholders, and run post-migration retrospectives.

March 4, 2024
Engineering Leadership Strategy

The Real Cost of Technical Debt

Quantifying technical debt in terms executives understand, and practical strategies for paying it down.

February 17, 2024
Product Operations Engineering

Building Internal Tools That People Actually Use

Why most internal tools fail at adoption and how to build ones that integrate into existing workflows.

January 21, 2024
Marketing AI Direct Response

Direct Response Marketing in the AI Era

What changes and what stays the same when AI meets direct response marketing at scale.

December 14, 2023
Marketing Operations Performance

Managing a $2M Monthly Ad Spend

Budget allocation frameworks, real-time optimization, and reporting that drives decisions at scale.

November 7, 2023
Leadership Career Engineering

From Developer to CTO: What Changes

The hardest skill shifts when moving from building software to leading the people and strategy behind it.

October 19, 2023
Email Deliverability Infrastructure

Cracking the Code: Mastering Email Authentication (Part 2/3)

Dedicated IP addresses, sender reputation monitoring, and reverse DNS setup for email deliverability.

September 25, 2023
Email Deliverability Troubleshooting

Cracking the Code: Diagnosing Email Problems (Part 1/3)

Checking email content, verifying sender reputation, and ensuring proper server configuration.

September 18, 2023
Operations Remote Work Leadership

Operational Excellence in a Remote-First World

Async communication, documentation-driven collaboration, and measuring output over activity in distributed teams.

September 11, 2023
E-commerce Conversion Customer Experience

Revolutionize Your Abandoned Cart Strategy

Multi-channel approaches to cart recovery including telesales integration and personalized follow-up.

August 31, 2023
Operations Strategy E-commerce

The Multi-Imprint Challenge: Running Parallel Brands

Shared infrastructure vs brand independence, data isolation, and knowing when to merge or keep separate.

August 4, 2023
SMS Marketing Branding

The SMS Marketing Landscape

Branded SMS setup, comparison of short link platforms, and creating memorable text campaigns.

July 31, 2023