170: Keith Jones: OpenAI’s Head of GTM systems on building judgement with ghost stories, buying martech with cognitive extraction and why data dictionaries prevail

What’s up everyone, today we have the pleasure of sitting down with Keith Jones, Head of GTM Systems at OpenAI. Also just a quick disclaimer that Keith is joining the podcast as Keith the technologist and human, not the employee at OpenAI. The views and opinions he expresses in this episode are his own and do not represent OpenAI.Summary: The best martech buying process isn’t a spreadsheet. It’s a cognitive extraction exercise.Keith Jones asks stakeholders to write what they want, say it out loud, and then feeds both into GPT to surface what actually matters. That discipline applies to agents too. Most teams chase orchestration before they have stable logic, clean data, or working workflows. Keith’s bet? The future of SaaS is fewer tools, built in-house, coordinated by agents not a graveyard of dashboards pretending to be automation.Why Sales Ops People Who’ve Actually Sold Have the Sharpest KnivesKeith Jones did not set out to work in sales operations earlier in his career. He landed in it sideways, like a lot of the best people in ops do. He was hired with the catch-all title of “Business Operations Associate,” which could mean anything or nothing, depending on the day. His job, in practice, involved forecasting bookings and revenue in Excel based on shipping data. No one told him he was in sales ops. No one even used that phrase. If someone had asked him whether he wanted a career in sales operations, he wouldn’t have known what they meant.The company later shifted him into a field sales role. They were trying to grow the team internally, so they dropped him into the southeast region and told him to start talking to CIOs and chief nursing officers. He moved to Atlanta and started selling. That job was hard in a way that most people who build systems for sales teams never understand. The structure was just enough to keep things moving, but not enough to support real learning. He had a quota, a few tools, and a manager who held weekly one-on-ones. There was no real training. No consistent coaching. No safety net. If he wanted to make it work, he had to figure it out himself.That experience never left him. Now that Keith leads systems for go-to-market teams, he still thinks about what it felt like to sit in a seller’s chair. Every tool that didn’t work, every field in Salesforce that meant nothing, every process that made his job harder stuck with him. He builds differently because of that.> “You’re given a quota, a few tools, some vague expectations, and then shoved into the wild.”The biggest disconnect he sees in GTM systems comes from people who have never sold anything. Many of the systems designed to help sales teams are built by career admins or operations specialists who’ve never had to ask for a purchase order or explain why a deal fell through. These people often optimize for what the business wants, not for what the seller needs to survive the quarter. Keith doesn’t speak about this in abstract terms. He lived through it.After his healthcare role, he joined a startup in Atlanta as employee number eight. He came in as an account executive, but quickly became the go-to person for explaining the product. He wasn’t the most technical person, but he could speak the language. That mattered. As the company grew and new reps joined, Keith found himself teaching them how to explain the product to customers. He was still selling, but he was also building shared knowledge. That part felt natural.Then his CEO pulled him into a room and told him something blunt. “You’re really bad at cold calling. You don’t even do it.” Keith agreed. He hated that part of the job. As an introvert, it never felt right. But the CEO followed up with something more important. “You know the product better than anyone else on the floor. I think you should be our first sales engineer.” Keith said yes immediately.There was one more thing. The Salesforce admin had just quit, and the CEO asked if he wanted to learn Salesforce too. Keith said yes to that as well. That moment when he stepped into a role that combined technical depth with operational design set the course for everything that came next.Today, he leads systems at a scale that touches thousands of sellers. He remembers what it felt like to sell without support, and he refuses to push that experience onto others. He builds tools that actually work because he knows what failure feels like.Key takeaway: Sales ops works best when it is built by people who have actually sold. If you want to build tools that sellers will use, you need someone who has lived with the friction of broken ones. Sellers do not care about elegant reporting architecture if the CRM slows them down. They care about speed, clarity, and context. Hiring operators who have carried a quota gives you an unfair advantage. They remember how it felt to lose time chasing bad leads or cleaning up messy data. That memory turns into better workflows. You can teach someone ...