If you’re in tech in 2026, you’re either at the beginning of your career, or at the end of it (there is no other option)

[Weekly GTM round-up] A CRO building an AI-native revenue org, 39% of AI companies are hiring SDRs, Trigify joins HubSpot, and a GTM Eng role at Navan

Sep 25, 2026

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Happy Friday! 🌞

We’re back with another edition of the GTM Weekly Round-up: a (bite-sized) editorial plus a few links that are worth your time.

Let’s diveee right in.

Over the last two years, I have re-skilled in a more significant way than ever in my career. More than when I first learned what ‘SaaS’ meant, at the SF startup where I was the first employee and we grew to 100 employees in 3 years. More than when I become a SaaS founder and raised venture capital. Re-skilling at this stage in my career is really hard and scary and tiring and… FUN. It’s the most fun I’ve had in at least five years. And I want to argue why you should choose the white pill too.

Today’s post is not to be alarmist. I have no “AI course” to sell you.

Also, in all honesty, I’m writing this just as much for myself. Because, I still have a long way to go on this journey of re-skilling myself. I feel behind, even though I’ve invested 10s of hours each week for the last 100 (!!!) weeks.

For anyone who is going to retire in the next 10 years, they probably don’t need to learn how to adapt in the AI era. For anyone who is in their first 10 years of their career, they’re probably learning how to use AI without questioning if they ‘need’ to. I’m somewhere in the middle, like many of you reading. Which means, I have to actively choose to re-skill myself.

This tweet sums up the fork in the road right now:

Aviel goes on to say, in another post:

You are not mid or late-career, you are just getting started.

If you can stomach that I have some REALLY good news for you. The future looks awesome and you're going to do something great.

I don’t want to act out of fear (like “learn AI or you’ll fade into irrelevance!”).

Instead, I want to act out of excitement. Out of curiosity. Out of optimism!

I’m choosing to take the white pill.

That doesn't mean pretending the disruption isn't real (I subscribe to rational optimism). It means believing that what comes next can be better than what came before. AI is going to automate parts of our jobs. Some of those will be tedious tasks we're happy to drop. Others will be things we've spent years getting good at, maybe even things we love doing. DHH's take on coding is a useful way to think about it as it starts to hit go-to-market.

He said he’s moving from being a professional programmer to being a professional maker. I think something similar is about to happen in go-to-market. The job isn't disappearing. The job is changing. The people who embrace that change will move up the stack, spending less time on manual execution and more on judgment, creativity, strategy, relationships, and orchestrating AI to accomplish things that previously required entire teams. You can look at that future and mourn what's being lost. Or you can get excited about what's being gained. I'm choosing the latter.

Please watch this 2-min clip from this week, where DHH declared the end of hand-writing code at Rails World 2026:

AI has transformed software engineering.

AI has transformed customer support.

And now, AI is in the process of transforming go-to-market.

Practical examples if you’re in go-to-market today

CRO: build reports (or a personal “RevOS”) in Claude Code like Tim.
Growth/GTME: build a custom harness+UI like Cursor (with ChatGTM) or XBOW’s internal GTM system.
RevOps: build an agent repo in GitHub like Nikko from Hightouch.

Be glad you had the opportunity to “chisel that prospect email by hand.” And what a privilege to have been there when we did it all by hand. And now, to be here, at the exact moment where we switch over to the new way of working.

Choose the white pill.

Weekly GTM Round-up:

Niroshan, CRO of XBOW ($1B security company started in 2022) on how they’re building an AI-native revenue org. We covered it on Tuesday: How XBOW’s team built one of the most sophisticated internal GTM systems I’ve seen.
Trigify (a signal platform focused on social engagement) announced it’s joining HubSpot. The second signal/intent provider that HubSpot has picked up (Warmly being the other one, a few months ago). Consolidation szn continues.
Josh Braun is one of my favorite voices on outbound/messaging/sales. This week he reminded me why I like his framing so much:
Jacob has been talking about context and taste for a long time now. I think many are going to realize the importance of these things (and tools like Clearskies) in the next year or so.
My friend, Andrew McGuire, recently joined Navan to continue up-leveling their revenue engine. He’s hiring a Senior GTM Engineer. My favorite line from the jd: Implement the controls required for production agents, including evaluations, human review, observability, error handling, permissions, auditability, sensitive-data safeguards, and rollback paths.
Reach out to Andrew and let him know I sent you.
Jevon’s paradox strikes again!
This was my favorite thing I read this week (it’s a super easy ~5 min read) Moats & the Barbell-ification of Software, by Mike Vernal of Conviction.
The general thesis is that software moats are shifting, and you either need to be the big player in a space (doing everything, aka compound startup) or be a small company by design.
I am already seeing this with CROs like Niroshan (XBOW), Tim (Hatch), Kyle (Owner), and Stevie (Vanta) living in the future (watch DHH’s full keynote here).
The Deal Director@thedealdirector
In less than 24 months there will be a clip of a high profile CRO explaining this reality to a (much smaller) room of sales reps.
DHH @dhh
There's nothing kind about letting good people live in a fantasy world that no longer exists. You have to tell them, even if it hurts. Because the sooner they accept reality, the sooner they can adapt to the future.
12:49 PM · Sep 24, 2026 · 358K Views
45 Replies · 180 Reposts · 2.44K Likes