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    Revenue Leadership12 min read17 Oct 2026

    What OpenAI's Former Head of GTM Systems Would Automate, and What the ANZ Job Ads Say About GTM Engineers

    Ricky PearlBy Ricky Pearl · Co-Founder

    OpenAI's former head of GTM systems on what to automate, Clay, and whether AI replaces GTM engineers. Plus what 19 ANZ GTM engineer ads actually ask for.

    What OpenAI's Former Head of GTM Systems Would Automate, and What the ANZ Job Ads Say About GTM Engineers

    Keith Jones joined OpenAI in late 2023, when the GTM organisation was under 100 people and the company already had more than a billion dollars on the books. By the time they left, nearly three years later, that org was more than 1,200 people around the world. Keith built and ran the GTM systems underneath it.

    This week they did an AMA on r/gtmengineering. It's one of the more grounded things I've read on GTM engineering this year, mostly because it's so unglamorous. No 40-step agent swarm. A few simple tests for what to automate, a lot of respect for salespeople, and a willingness to say the quiet part about Clay and the GTM engineer title.

    Below is what Keith said, grouped by theme. After that, what it means if you're hiring for this in Australia or New Zealand, with numbers from the GTM engineer ads we've tracked since April.

    How OpenAI Decided What to Automate

    Keith used three tests: volume, consistency and risk.

  1. Volume. Is this something people do hundreds or thousands of times, on repeat? That's the strongest signal.
  2. Consistency. How predictable is the outcome? If everyone already handles it the same way and the human judgement adds little, it's a candidate.
  3. Risk. What happens when it's wrong? Does a customer churn, does the forecast break, or can a person spot the mistake and reverse it in a minute?
  4. The point is that they compound. High volume, predictable outcomes and survivable mistakes together make the best targets.

    The worked example was close dates on opportunities in the CRM. Every sales team has to keep them current, reps are creatures of habit (plenty just push the date to month end), and the real decision is usually only "this month, this quarter, or later". An agent with the deal history, notes and call recordings can make that call. But Keith wouldn't hand it over in one go: start with recommendations, move to automatic updates where confidence is high, and keep exceptions for a human.

    "Automation doesn't have to be binary."

    >

    Keith Jones

    That one line is the most useful idea in the thread. Autonomy gets earned in stages. It isn't switched on because the tech can technically do it.

    What They Actually Built

    When asked which systems mattered most, Keith picked two. Neither is exotic.

    Agentic qualification. Traditional lead scoring is a deterministic points model, which flattens a prospect into a handful of attributes. Replacing it with an agent let OpenAI reason across structured and unstructured information about a prospect. The structure and consistency stayed. What changed was how the qualification decision got made.

    A lightweight GTM assistant. Before everything got called an agent, the team built a simple assistant that nudged sellers: meeting follow-ups, quick digests, calendar changes, contextual reminders. What excited Keith was where it could go next. Instead of summarising your last call, it could notice a colleague just closed a deal with the same pain points and put the two of you in touch.

    One commenter's reaction was the right one: every vendor is selling extremely complex agentic workflows, and the person who did this at OpenAI scale stuck with the basics.

    Where the Human Stays

    Asked whether GTM engineering should focus on prospect intelligence rather than automating outreach itself, Keith agreed completely and went further. Augmentation should be the starting point for applying AI to nearly any job.

    Data entry, research, qualification, admin and internal process? Automate it hard. The conversation and the relationship stay with the seller, because a deal is a commitment between businesses and the people in them.

    The test Keith offered for outreach is a good one to steal:

    "If you feel even an iota of hesitation... that's your signal that human judgment still belongs in the process."

    >

    Keith Jones

    If a rep would be happy for an LLM to write and send the message with no involvement from them, automate it. If they'd want to proofread it first, the workflow hasn't earned autonomy yet.

    There's a warning in there for builders too: don't let how abstract your own role is make you forget the people you're building for. Being able to automate something doesn't mean you've earned the right to remove the human from it.

    The Stack: Capabilities First, Vendors Second

    Keith's advice was to stop thinking about vendors and list the capabilities you need:

  5. a system of record where people and agents share the same view of the business
  6. a data layer (warehouse, lake or lakehouse) where it gets consolidated
  7. analytics that make it readable
  8. communications infrastructure between people, systems and agents
  9. somewhere to host and run the apps, automations and agents
  10. the connective tissue: integrations, orchestration, identity, permissions, governance and observability
  11. Then check which of those your current stack already covers and find the real gaps. A pile of fashionable AI tools is not an AI-capable GTM architecture.

    The same logic came up when someone asked whether it's still smart to build heavily in Salesforce and HubSpot. Learn the features as concepts first and platform settings second. If you understand sharing rules or scoring models as ideas, you'll know what has to exist when you end up on a home-built CRM.

    Clay, and Whether GTM Engineering Is a Rebrand

    Someone asked why the industry is obsessed with Clay, given most GTM engineer JDs read like "Clay specialist". Keith's answer: because that's exactly what Clay set out to do. The rise of the GTM engineer is as much a story of category creation and good marketing as a new way of working. Clay saw the opportunity, helped name it and built a community around it.

    There's substance under the hype. Clay made multi-source enrichment and orchestration accessible to people who'd previously have needed several vendors and an integration engineer. Keith adopted it in early 2024, when they were still a team of one at OpenAI, to get multi-source enrichment into production fast.

    But knowing a platform isn't the job.

    "Knowing how to operate a platform is valuable, understanding how to design reliable, scalable systems that solve business problems is considerably more valuable."

    >

    Keith Jones

    And then the spicy bit. Asked whether AI will replace GTM engineers, Keith said no, not any time soon, but added that a big share of what we call GTM engineering is work product managers, business systems people and RevOps have done for years, now with very different tools at much greater speed. "Humans love a good rebrand."

    The more capable the systems get, the more you need people who understand what you're asking them to do and whether you should be doing it at all. Fewer repetitive tasks, more design and judgement. Eliminating tasks and eliminating professions are different things.

    The Rest of the Thread, Quickly

  12. Small businesses: be surgical. Find the one manual process that holds you back most, automate it, and use the time you get back to fund the next one. If a simple deterministic workflow solves it, use that. Keith compared it to chess: take a piece of the board, consolidate, advance.
  13. Tech stack vs people: the biggest credit went to OpenAI's sales managers and their teams, who built a playbook for a product changing almost as fast as they could sell it. Tech and data quality are force multipliers. And yes, reps complained about wrong employee counts every day. Data quality is never done.
  14. Content and outbound: expect a flood of automated volume. Don't confuse automating the production of something with automating its effectiveness. Slop existed before AI; we just make it faster now.
  15. Agencies: the threat is real for anyone selling commoditised execution. Move up the value chain.
  16. Does OpenAI even need GTM? "Ask Anthropic." Inbound is strong, but you still have to step into the ring.
  17. Starting again: Keith would have spent more time early on designing how the GTM systems team itself would work, instead of only fighting the fire in front of them.
  18. Why they left: burnout, honestly put. Three years at that pace was a marathon. Keith now runs an independent research and advisory practice, drawing on earlier years as a Gartner analyst, and is building a tech publication.
  19. What This Means for Hiring GTM Engineers in ANZ

    Keith's take is that GTM engineering is still being defined and overlaps heavily with RevOps and business systems. Our job ad data says ANZ is even earlier than that.

    We track GTM job ads across LinkedIn, SEEK and company careers sites. Between 1 April and 16 October 2026 we counted every direct-employer ad in Australia and New Zealand with "GTM engineer" or "go-to-market engineer" in the title. We removed reposts of the same role, recruiter ads and our own ad.

    GTM engineer titlesRevOps, sales ops, marketing ops and GTM systems titles
    Unique ads, 1 April to 16 October 202619~1,000
    Employers16about 800
    Ads that name Clay6 of 19under 1% (9 ads)
    Ads that name HubSpot or Salesforce12 of 19about a third

    Three things stand out.

    1. The title barely exists here yet. Nineteen roles in six and a half months, at 16 companies, including SafetyCulture, UpGuard, Speechify, PitchBook, Podium, Lorikeet and pay.com.au. Over the same period, about 1,000 ads went out under RevOps, ops and systems titles. If you're hiring for GTM engineering in ANZ, most of the people who've done the work don't have the title on their LinkedIn. Search the RevOps and systems pool.

    2. It isn't a Clay job in ANZ. Clay appears in a third of local GTM engineer ads. A CRM appears in close to two thirds. That matches Keith's point: the tool is a skill, not the role. An ad that reads like a Clay certification will screen out the systems thinkers you actually want.

    3. A few companies are building teams, not hiring a lone wolf. SafetyCulture and UpGuard have both advertised a manager of GTM engineering alongside individual roles. That's the step Keith said they wished they'd taken earlier at OpenAI: designing how the team works, not just fixing the next problem.

    On pay, too few of these ads print a salary to say anything with confidence, and the ones that do are mostly recruiters. For ranges, see our guide on how to hire GTM engineers.

    Interview questions borrowed from the AMA

    If you're hiring a GTM engineer, Keith's thread doubles as an interview guide:

  20. "Walk me through something you chose not to automate, and why." You're listening for volume, consistency and risk, in some form.
  21. "How did you roll out an automation that could write to the CRM?" Good answers sound like recommend first, then auto-update when confidence is high, with exceptions going to a human.
  22. "Describe a stack you built in terms of capabilities, not vendors." Can they talk about the system of record, the data layer and permissions without naming a single tool?
  23. "Tell me about a workflow you rebuilt when the tool changed." This separates people who know concepts from people who know menus.
  24. "Which part of a rep's week would you never automate?" If the answer is "nothing", keep looking.
  25. Hiring a GTM Engineer in Australia or New Zealand?

    Most of the strongest GTM engineers in ANZ are sitting in RevOps, sales ops and business systems seats under a different title. We find and vet them with people who've built these systems, and our performance contract means you pay monthly and billing stops if the hire leaves.

    Hire GTM Engineers with Pointer

    Frequently Asked Questions

    Ricky Pearl

    Written by

    Ricky Pearl

    Co-Founder, Pointer Strategy

    Former Head of Commercial Sales. Founder & CEO (exited). 6 years building recruitment and enablement systems for ANZ's top SaaS companies.

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