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From the Headways team

Research and insights on AI workforce transformation, judgment assessment, and closing the gap between how your best people use AI and everyone else.

The AI Skill Marketplace Is Coming. Here Is What Is at Stake.
June 6, 2026·8 min read
AI MarketplaceSkill CreatorsCreator Economy

The AI Skill Marketplace Is Coming. Here Is What Is at Stake.

The GPT Store failed because OpenAI owned the platform. The AI agent skills marketplace will succeed for the opposite reason. Open standards, portable formats, and what creators should be doing now to position for when the monetization layer arrives.

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Why Most AI Buyers Do Not Know What They Are Buying (Yet)
June 6, 2026·7 min

Why Most AI Buyers Do Not Know What They Are Buying (Yet)

The enterprise AI procurement crisis is not a vendor problem; it is a buyer literacy problem. Gartner says 40% of agentic AI projects will be canceled by 2027. The cause is buyers who cannot specify what they are buying. Here is the vocabulary that fixes it.

Enterprise AIAI ProcurementBuyer Education
The Cofounder Skill Stack: How to Split AI Work When You are Two People
June 6, 2026·8 min

The Cofounder Skill Stack: How to Split AI Work When You are Two People

The hot take is wrong. AI did not make the non-technical cofounder obsolete; it made the technical cofounder more replaceable. Here is the new split for two-person founder teams, and the three conversations every cofounder pair should have this month.

CofoundersAI Cofounder WorkflowFounder Teams
AI Sales Plateau: Why Your Reps Stop Improving at Month Six
June 6, 2026·7 min

AI Sales Plateau: Why Your Reps Stop Improving at Month Six

Your AI sales tools did not fail. They created a two-tier sales team, and you do not yet know which half you are running. The Gong 77% revenue gap, the BCG 23% regression, and what actually unlocks the second leg of performance.

AI SalesSales EnablementGTM
The Two-Person AI Studio: A Playbook for Founder Teams in 2026
June 6, 2026·8 min

The Two-Person AI Studio: A Playbook for Founder Teams in 2026

Lovable hit $10M ARR in 2 months. Cursor crossed $1B. Two people can ship what used to require fifteen. The new bottleneck is not the code; it is the 40 micro-decisions a day that used to require a team meeting.

AI Micro StartupFounder TeamsVibe Coding
Guided AI Sessions vs Self-Paced Learning: Which Actually Works?
April 27, 2026·5 min

Guided AI Sessions vs Self-Paced Learning: Which Actually Works?

Self-paced AI courses have 5-15% completion rates. Guided sessions with real deliverables hit 94% behavior change. Here is why the format matters more than the content.

Guided LearningSelf-PacedTraining
Enterprise AI Upskilling: A Buyer's Guide for 2026
April 26, 2026·4 min

Enterprise AI Upskilling: A Buyer's Guide for 2026

LMS, certification, consulting, or platform? Compare the four approaches to AI upskilling and find the one that actually produces behavior change.

EnterpriseBuying GuideAI Upskilling
From AI Champion to AI Culture: Scaling What Your Best People Do
April 25, 2026·5 min

From AI Champion to AI Culture: Scaling What Your Best People Do

Every org has AI champions in the top 10%. The challenge is making their workflows available to the other 90%. Here is a framework for scaling individual excellence into organizational capability.

AI CultureChampionsScaling
The AI Judgment Gap in Finance: Why Your Analysts Need More Than Prompt Training
April 24, 2026·5 min

The AI Judgment Gap in Finance: Why Your Analysts Need More Than Prompt Training

Finance teams use AI for DCF validation, risk assessment, and audit prep. But prompt training misses the point. Judgment, knowing when to trust and when to override, is the real skill.

FinanceAI JudgmentAnalysts
How to Build Your Organization's AI Workflow Library
April 23, 2026·5 min

How to Build Your Organization's AI Workflow Library

A step-by-step guide to capturing, organizing, and sharing AI workflows across teams. Turn tribal knowledge into a searchable, reusable asset.

WorkflowsKnowledge ManagementBest Practices
Measuring AI ROI Beyond Productivity: The Behavior Change Metric
April 22, 2026·4 min

Measuring AI ROI Beyond Productivity: The Behavior Change Metric

Hours saved is the wrong metric. The real question is whether people work differently after training. Here is how to measure behavior change and present it to the board.

ROIMetricsBehavior Change
The Senior-to-Junior Knowledge Transfer Problem in the AI Era
April 21, 2026·5 min

The Senior-to-Junior Knowledge Transfer Problem in the AI Era

Senior AI workflows are invisible. They live in muscle memory, not documentation. When seniors leave, that knowledge walks out the door. Structured capture is the solution.

Knowledge TransferSenior-JuniorRetention
Why AI Certificates Don't Change Behavior (And What Does)
April 20, 2026·5 min

Why AI Certificates Don't Change Behavior (And What Does)

Certificates measure completion. They do not measure whether employees actually work differently. Here is what behavior change requires and how to build training that produces it.

CertificatesBehavior ChangeTraining
The L0-L3 AI Proficiency Framework: A Practical Guide for Enterprise Teams
April 19, 2026·5 min

The L0-L3 AI Proficiency Framework: A Practical Guide for Enterprise Teams

Stop asking "are you using AI?" Start asking "what level are you at?" A four-level progression model that reframes adoption from binary to spectrum.

FrameworkProficiencyAI Adoption
What Ramp's Glass Teaches Us About Enterprise AI Adoption
April 18, 2026·4 min

What Ramp's Glass Teaches Us About Enterprise AI Adoption

Ramp built an internal AI tool called Glass that achieved 99.5% adoption. Most companies cannot build their own. Here is what we can learn from their approach.

RampGlassAI Adoption
Why 82% of AI Training Programs Fail to Change How Employees Actually Work
April 17, 2026·5 min

Why 82% of AI Training Programs Fail to Change How Employees Actually Work

59% of enterprise leaders report an AI skills gap despite 82% offering training. The problem is not content. It is that courses measure completions, not behavior change.

AI TrainingEnterpriseWorkforce
How to Measure AI Judgment, Not Just AI Knowledge
April 16, 2026·6 min

How to Measure AI Judgment, Not Just AI Knowledge

Quizzes test what people know about AI. They do not test whether someone can catch a hallucination, validate a source, or know when to override. Here is a framework that does.

JudgmentAssessmentAI Skills
The CAIO's Guide to AI Upskilling ROI: Beyond Completion Rates
April 15, 2026·4 min

The CAIO's Guide to AI Upskilling ROI: Beyond Completion Rates

Only 21% of leaders see significant ROI from AI investments. The problem is not the tools. It is what you are measuring. Here is how to present AI training ROI to the board.

CAIOROIEnterprise
Capturing How Your Best People Use AI Before They Leave
April 14, 2026·5 min

Capturing How Your Best People Use AI Before They Leave

Senior employees develop AI workflows nobody else can replicate. When they leave, that knowledge walks out the door. Here is how to capture it in 15 minutes.

Knowledge TransferRetentionWorkflows
AI Upskilling in 2026: Why Generic Courses Can't Close the Skills Gap
April 13, 2026·5 min

AI Upskilling in 2026: Why Generic Courses Can't Close the Skills Gap

AI training spending is up 28% year over year, but 56% of workers still have zero formal training. Generic courses are not the answer. Role-specific workflow training is.

AI Upskilling2026Skills Gap
Introducing Headways: AI Workforce Upskilling That Produces Behavior Change
April 12, 2026·5 min

Introducing Headways: AI Workforce Upskilling That Produces Behavior Change

Headways captures how your best people work with AI, then guides everyone else through those workflows while producing real deliverables and measuring judgment.

LaunchAIUpskilling
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