Navigating Career Transitions in Sales and AI

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 Knives

Keith 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 how to configure Salesforce. You cannot teach someone how it feels to miss your number because your systems were designed by someone who never had one.

The Difference Between GTM Ops and GTM Systems

When people talk about GTM operations, most of them blend it with GTM systems like it’s all one job. It's not. They share a Slack channel, maybe a budget, and definitely a few dashboards, but the actual work is completely different. Keith has lived on both sides of that line. At OpenAI and before that at Mural, he ran GTM systems. Back at Gartner, he saw how every company defines these roles differently, sometimes with intention, sometimes out of inertia. But when he breaks it down, the split is actually pretty clear.

GTM ops exists to support the field directly. That means helping sellers, marketers, and customer success teams get their work done. Think enablement, process design, live troubleshooting, deal support, and training that doesn’t feel like a waste of time. These teams sit next to the people they’re helping and shape operations based on actual conversations and feedback.

GTM systems is a whole different rhythm. These are the people writing the workflows, building automations, owning the CRM, and threading together tools that are supposed to work seamlessly but rarely do. They are not front-facing. They are deep in the guts of your tech stack. They touch code, configuration, architecture, and logic trees that determine whether your rep gets the right lead or a ghost contact from 2017.

> “We rely heavily on our ops colleagues to feed us guidance from the field so we can build the right solutions. That’s the balance that works.”

Keith’s favorite model is one where GTM ops and GTM systems are separate but inseparable. Not one inside the other. Not one reporting into the other. Two teams, side by side, solving for different parts of the same outcome. Ops listens and adapts. Systems builds and scales. When that rhythm is right, sellers feel supported without even knowing why. When it breaks, people stop trusting the process and start hacking together their own.

He makes an important distinction when talking about marketing ops. Unlike sales ops, which skews toward operational execution, or systems, which skews technical, marketing ops often lands in the uncomfortable middle. It needs to speak both languages. You might be setting up nurture logic in Marketo one hour and then coaching a team through campaign QA the next. Keith sees it as a dual-mode function, one that requires:

Operational discipline to support marketers with templates, briefs, budgets, and targeting logic
Technical fluency to build and maintain systems that track performance across platforms

The tension between systems and ops is real. I’s not a fight. It’s a rhythm. And when ...