Resources
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Covering digital transformation and innovation in fintech, healthtech, and media.
Build vs Buy in 2026: How AI is Changing Economics (But Not the Way You Think)
My colleague Frank recently posted a provocative idea in our internal Slack channel: “AI killed the SaaS model” (a play
Your AI Strategy is 100% Correct and 0% Actionable. Here’s Why.
An AI customer service agent at Cursor, an AI-powered coding assistant, invented a company policy that didn’t exist. When users
Compliance Theatre Won’t Keep You Safe, Here’s What Will
The compliance document arrives: “You shall protect your endpoint.” “You shall have a cyber security policy.” “You shall monitor your
The ‘Five Times’ Rule: a CEO’s Framework for Deciding What to Automate
I’m going to risk an ‘Old Man Yells at Cloud’ moment here: every year, I spend time collecting and summing
The Progress Illusion: Why Your Strategic Initiatives Burn Money Without Creating Value
Your technology team reports 80% completion. Your project tracking dashboard is nearly all green. Your quarterly demos are well-attended. Everyone
From Assessment to Action: The Document That Gets Technology Projects Funded
In my previous article on technology assessments, I explained how to diagnose what’s actually broken in your technology platform. Companies
The API-Driven Enterprise: Why Your Digital Transformation Needs a Communication Architecture (Not Just a Technology Stack)
Digital transformation initiatives don’t fail because of bad technology choices. They fail because the business can’t coordinate the work. Digital
AI Isn’t Software: Why CEOs Keep Getting the Business Case Wrong
Your CFO approved the AI investment based on a clear ROI calculation. The model was going to improve decision-making, reduce
When Flexibility Matters More Than Structure—and Vice Versa
Choosing a Content Management System (CMS) approach isn’t just a technical decision—it’s a strategic one, balancing speed, autonomy, and long-term
How Smart CEOs Use Technology Assessments to Diagnose Their Issues
Imagine you’re the CEO of a mid-sized SaaS company with around $100 million in annual recurring revenue. You’re beset by
Beyond the Hype: How CEOs Can Build Digital Transformations That Actually Deliver
When planning digital transformations, CEOs have a powerful opportunity. They can dig deep to understand where true business opportunity lies
How to Protect Your Business from the Next AWS Outage with Multi-Region Design
On October 20, 2025, a major cloud incident rocked the backbone of the internet. AWS reported “increased error rates and
7 Digital Transformation Traps And How To Avoid Them
Here’s a sobering thought: depending on where you get your statistics (Deloitte, McKinsey, Forbes or HBR), somewhere between 70% and
How to Manage Product Innovation During Platform Modernization
If you’re a CPO stuck between delivering new features and modernizing legacy systems, this article offers a way out: the
Metrics That Matter: How To Measure What Actually Drives Product Success
Every product organization is drowning in data. Sprint velocity, story points completed, lines of code written, deployment frequency – the
The Executives’ Guide To Not Getting Disrupted: Why Your AI Strategy Determines Your Survival
You probably saw some of the news reports earlier this year: media companies across the country, drunk on the hype
The Ignored Business Requirements That Are Sabotaging Your Product Roadmap
Focusing exclusively on developing new features might seem like the fastest way to achieve your product goals, but by ignoring
How to Prepare Your Business for the Agentic Web (Without Betting the Farm)
If you’re being asked about your strategy for agent-based capabilities, this is what you need to know: there’s a good
What I Learned From LeetCode
LeetCode is an online coding site designed to challenge its users with algorithmic programming tasks commonly associated with the interviewing
The 2am Question Every CEO Should Ask About Their Data
Here’s a question that should keep every CEO awake at night: Do you know where your data is, and are
Cutting Through The AI Hype: The Real Business Questions Every CEO Should Be Asking
Back in 2001, my team and I were sitting in a boardroom in Los Angeles, demonstrating what we thought was
Beyond Bottlenecks: How CEOs Can Apply The Theory Of Constraints To Drive Growth
If you’re struggling to grow your business, you only really have two options. One is to systematically find the root
The Business Cost of Technology Debt: Why Small Changes Take Too Long and What CEOs Can Do About It
Have you ever heard this before? “I just need a small change to this feature.” Or perhaps: “How hard could
Parameter Store and Secret Manager Integration with Spring Boot
We need to securely store and share sensitive credentials, passwords, and configuration information separately from our source code in Parameter
Your Scaling Problems Aren’t Technology Problems
Scaling challenges represent existential moments for mid-market companies, and failing to address them can be fatal to the business. If
Technology Consulting: Influencing Organizational Culture Beyond Technical Solutions
The role of a technology consultant might seem straightforward: provide analysis of and solutions to a customer’s tech-related problems. However,
Embracing a Culture of Data Curation: Unlock the Potential of Untapped Data Wealth
In today’s digital age, data reigns supreme as one of the most valuable assets for businesses across all industries. From
Proper Pagination with GraphQL
GraphQL has many advantages over REST interfaces, such as the ability to request specific fields, with relationships, and get only
What User Stories and ChatBot Prompts Have in Common
As a product owner, you want to convey to your team the context around a desired feature. Who is it
Start A New TypeScript Project Fast!
The AWS Project Development Kit (PDK) and projen, which it’s built on, can save you so much time during project