Jonathan Hessing

Managing Partner, ShooflyAI

Jonathan Hessing is a Managing Partner at ShooflyAI, where he helps mid-market businesses adopt custom AI employees, agents, and agentic operating systems they own. He writes about putting AI to work on real workflows, measuring ROI in time, cost, and revenue, and avoiding the traps that stall most AI projects.

Jonathan Hessing

AI Agents for Business: What They Are and What They Actually Do

AI vs Automation: What's the Difference and Which Do You Need?

Will AI Replace Bookkeepers? What Actually Changes

Will AI Replace Recruiters? What Actually Changes

The 100-Day AI Plan for Private Equity: A Value-Creation Playbook Portcos Own

AI Candidate Screening and Credentialing for Staffing and Healthcare Agencies

AI Construction Estimating and Takeoff: Bid Faster, Win More

AI Month-End Close: How to Automate the Financial Close

AI Consultant vs. AI Agency: Which Should You Hire?

AI for Accounting Firms: Cut the Close and Reclaim Billable Hours

AI for Construction Companies: Bid More Work Without Adding Estimators

AI for Healthcare Staffing Agencies: Place More Clinicians Per Recruiter

AI for Higher Education: Automate Enrollment Ops Without a Black-Box Vendor

AI Implementation Roadmap for Mid-Market Companies: A Sequenced Plan

AI Readiness Assessment Cost: What You Pay and What You Get

AI Strategy for Mid-Market Companies ($10M to $75M): The Operator's Playbook

AI Value Creation in Private Equity: A Program Your Portfolio Companies Own

AI Without Vendor Lock-In: How to Own Your AI System

Build vs. Buy vs. Own: How a $10M to $75M Company Should Adopt AI

How Much Does Custom AI Cost for a Business? An Honest Breakdown

How to Measure AI ROI: The Metrics That Actually Matter

Is Custom AI Worth It for a Mid-Market Business?

AI Operating Assessment: What It Is, What It Includes, and What It Costs

Who Maintains Custom AI After It Is Built? The Honest Answer

Why Most AI Pilots Fail (and the Diagnostic That Prevents It)

The AI Employee Emails You Missed

Proactive AI Agents: The Real Business Upgrade

Vibe Code Hardening for Secure AI Code

AI Employee Fixes WordPress Email After Migration

Renting AI vs. Owning AI

What Is an Agentic Operating System and Why It Matters

Stop Chasing “Everything” With AI

Why Most AI Projects Stall (and What the Successful Ones Get Right)

The Benefits of AI for Small to Medium-Sized Businesses

No-Code AI: Transforming Artificial Intelligence

Demystifying Machine Learning: A Beginner’s Guide

How AI is Changing the Social Media Marketing Landscape

Breaking Down Google’s Whitepaper on AI Agents

What is Retrieval-Augmented Generation (RAG) in AI?