Justin Pennington

You're paying someone to be the API your stack never built. The person copying status between CRM, ERP, and the dock board isn't a process quirk — they're your integration layer. New on Medium: medium.com/@justin-penningto… Full original: penningtonj.com/blog/stop-pa…

Most growing ops businesses don't have an integration layer. They have a person who copies status between tools and answers "where is that?" in Slack all day. That person is expensive middleware. penningtonj.com/blog/stop-pa…

Stop Handing Agents a Prompt. Hand Them a Job. Perplexity's new Teammates own ongoing work, not one-off chat sessions. Write the job description first: what it owns, what it can touch, and when a human has to say yes. penningtonj.com/blog/stop-ha…

Ask every AI vendor this before you give an agent write access: can I undo exactly what it did — and only that? New Hashnode piece, varied from today's penningtonj.com post on Dropbox's conversation-scoped undo. justinpennington.hashnode.de…

The bottleneck in most companies is no longer the person who does the work. It's the person who has to say yes. Approvals belong inside the workflow, not in Slack threads with no record. New on Medium: medium.com/@justin-penningto…

Dropbox's new agent ties every file change back to the conversation that made it, so you can undo just that work. If a vendor can't answer yes to undo, plan-first approval, and permissions the agent can't rewrite, keep the tool read-only. penningtonj.com/blog/if-you-…

Running AI agents in a seven-person company, the question isn't "can you trust it?" It's how much to trust it on each task. We track the edit rate. New on Dev.to: dev.to/justinpennington/trac…

Bid teams lose more deals before the RFP than after it. Most win-rate problems are qualification problems, not writing problems. Wrote this up on Substack: justinpennington.substack.co…

AI agents don't manage themselves. At a seven-person company, the real work is review cycles, deciding how much to trust each task, and catching the failure patterns early. New post: penningtonj.com/blog/ai-agen…

Salesforce is reportedly paying $2.7B for Cresta because phone calls rarely make it into the customer record. Fix that before you buy an AI phone agent. penningtonj.com/blog/the-pho…

Salesforce is reportedly paying $2.7B for Cresta because phone calls rarely make it into the customer record. Fix that before you buy an AI phone agent. penningtonj.com/blog/the-pho…

Before you put a software license next to a build quote, write down who gets to change each workflow next year. If you can't name a person, you're not ready to buy or build. New on Substack: justinpennington.substack.co…

AI agents can do the work now. The question is what they can touch, who owns them, and how fast you can stop them. Before adding another, write down its access, owner, log, and off switch. penningtonj.com/blog/every-a…

An AI agent you chat with is a tool you forget about. An AI agent with an assigned task, a due date, and a visible status is a teammate you can hold accountable. I wrote up why we put agents on the task board as assignees, not in chat sessions: dev.to/justinpennington/mode…

Most new systems don't fail on launch day. They fade a few weeks later, when training wears off and the team drifts back to the spreadsheet. I wrote up the seven questions I use to catch that drift early: medium.com/@justin-penningto…

A dock appointment is a promise to a carrier, a customer, and your own floor. A whiteboard can't keep that promise once the day starts slipping. I wrote up why dock scheduling has to live in software: justinpennington.hashnode.de…

I don't trust an AI tool that just hands me a confident answer. If it can't show its sources and reasoning so my team can check them, we don't ship it. linkedin.com/pulse/ai-should…

Fifteen SaaS logins isn't a system. It's a rental agreement with fifteen landlords. I wrote up a four-question audit for figuring out which part of your stack you should own and which you can happily rent: justinpennington.hashnode.de…

Software demos happen on a laptop with good wifi and two free hands. Real operators have one hand on a radio, the screen in the sun, and thirty seconds. That gap is where ops software gets adopted or abandoned. penningtonj.com/blog/operati…

Most rollouts hide a second project: integration. The ERP goes live, then six weeks later someone notices orders are still being retyped by hand. I wrote up how I scope it up front: map every arrow, pick direct vs hub, and treat error handling as the real job. dev.to/justinpennington/inte…