INSIGHTS

Strategy

Perspectives on AI strategy, implementation, and leadership in this category.

How New York's Accounting Firms Are Evaluating AI

How New York's accounting firms are evaluating AI for assurance and compliance. Most get the sequence wrong. This 90-day framework evaluates AI without pilotitis.

Issy · Aug 12, 2026

LONG READ·STRATEGY· 12 min read

AI Competitive Advantage for Mid-Market Leaders: Why Speed-to-Decision Beats Data Hoarding

AI competitive advantage mid-market firms miss has nothing to do with data volume. Decision velocity is the real moat. Here is the framework to close that gap.

Issy · Jul 19, 2026

Q&A·STRATEGY· 22 min read

Where to Start When You Have a Lot of Data and Want to Be AI-Native

You have a lot of data and want to be AI-native — where do you start, and what setup is cheapest while ROI is still unproven? A reference engagement on a 1.5 TB corpus, with cost models for CEOs and pipeline detail for CTOs.

Issy · Jun 29, 2026

Q&A·STRATEGY· 12 min read

Turning Data into Actionable Insights: The Information Architecture Question Leaders Get Wrong

Turning data into actionable insights fails when leaders skip information architecture. Here is the structural question every mid-market CEO must answer first.

Issy · Jun 27, 2026

Q&A·STRATEGY· 12 min read

Enterprise AI Architecture: Hubs, Harnesses, and Tenant Isolation

Enterprise AI is shifting from shared APIs to private, governed infrastructure. Hubs, harnesses, and tenant isolation are the three decisions that determine whether you scale safely.

Issy · Jun 11, 2026

LONG READ·STRATEGY· 8 min read

10 Lessons Being Learned as we make a 9-Figure Fire and Security Company AI-Native

Ten lessons we are learning as we put AI to work inside a fire safety and monitoring company. Five insights on the team and where the money hides. Five on the data, the ups and downs of the new AI hire, and the strategy that decide whether any of it works.

Issy · Jun 10, 2026

Q&A·STRATEGY· 9 min read

Why Value Pricing AI Consulting Matters More Than You Think

Value pricing in AI consulting aligns incentives: builders own outcomes, clients pay for results. Why developers beat traditional consultants at this game.

Issy · May 29, 2026

LONG READ·STRATEGY· 11 min read

How to Choose an AI Consulting Partner (Without Getting Burned)

91% of mid-market companies use AI, but 70% need outside help to maximize value. Here's the 5-point due-diligence checklist before signing any engagement.

Issy · May 24, 2026

LONG READ·STRATEGY· 15 min read

AI ROI for Mid-Market: Why 56% See Zero Return

AI ROI for mid-market needs workflow redesign and error accounting. 56% see zero return. Here's the formula separating real outcomes from theater.

Issy · May 18, 2026