Getting back to the This Week in GTM series, we did a few of these in late 2025 but as we ramp up media efforts, going to try to do a couple of these a month (and eventually, weekly).
The ones we did in 2025 for context (piece 1 and piece 2). Really enjoyed writing them and bringing it back.
My style is a little GSElevator/Litquidity meets tech sales.
Think of it as a combo of TBPN’s Run Of The Show + My First Million (specifically, Shaan’s 5 Tweet Tuesday) - sharing tweets from the week and riffing on them, specific to sales + startups + AI.
Was great having my friend, Glenn Rachlin, on this one who recently started as head of GTM @ OpenRouter - he’s equally as X-pilled as I am. A past guest of the podcast, great to see him make the move from crypto into AI.
If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.
What We Talk About
#1 - X vs. LinkedIn: The "Mullet" of B2B Social
I was motivated to get this series back up and running because GTM X/Twitter has been electric lately and has only fueled my screen addiction.
I posted on LinkedIn saying it was an electric day for GTM Twitter. Within an hour, my DMs were flooded with sales reps asking: "wait, what happened? what are you talking about?"
It was a massive reminder that 95% of traditional SaaS salespeople still aren’t on X - and if you are in AI (or want to break in), that’s a mistake.
The difference between the two:
It’s a mullet: formal in the front (LinkedIn), party in the back (X)
On LinkedIn, everything is sanitized, corporate, or some viral video your grandma would forward you
On X, people actually riff in real time, talk a little trash, and share what’s really happening behind the scenes.
Swim where the buyers and builders swim
Ever since Cursor, OpenAI, and the dev-tool wave took off, the entire engineering and AI founder ecosystem has lived on X (it was happening before then, but we now see team metrics where they are being forced to post, which means it’s becoming a lot of fun to watch + distribution is a moat)
If you’re selling to AI-natives - or trying to get hired at one - you need to be on the platform your buyers and founders read every morning
Walking the line on X
You have permission to talk a little trash on X as long as you keep it playful and never malicious
Case in point - I love Brian LaManna’s content, so I poked him a bit asking how we get him out of "Dino Jurassic SaaS" and into the AI-native trenches:
#2 - The Factory vs. Cognition Saga
Every once in a while a huge sports event or breaking news story drops and economists calculate how many millions of dollars in workplace productivity just evaporated.
I can guarantee you that all of AI GTM stopped working for at least three hours when this story broke.
Full disclosure before we dive in: we love folks on both sides of this. We’ve worked with Matan and the Factory team (helped place some of their founding AEs - shoutout Jack Larratt, Andy Taylor, and some others), and I have a ton of friends over at Cognition.
I have zero clue what the actual behind-the-scenes truth is here, so consider this pure commentary from the bleachers.
Here’s the play-by-play of how it unfolded in real time on X:
Step 1: Matan drops the bomb
Matan Grinberg, CEO of Factory, posts a statement announcing they are terminating legendary Snowflake CRO Chris Degnan from his role as Board Observer and Advisor for "unethical conduct involving Cognition":
Step 2: Seconds later, Chris Degnan announces he’s joining Cognition as CRO
Seconds after Matan’s tweet went live, Degnan drops his announcement that he’s coming out of retirement to be CRO at Cognition alongside his longtime Snowflake co-pilot Chad Peets:
Step 3: Scott Wu and Chris Degnan fire back
Minutes later, Cognition CEO Scott Wu and Degnan both reply publicly, saying Degnan wasn’t fired - he resigned on Monday to take the CRO seat at Cognition, and that Factory had actually tried to counter-offer him a full-time role:
Step 4: The VCs jump off the top rope (Vinod Khosla & Shaun Maguire)
one rule - no touching of the hair or face!
Usually boardroom disputes stay behind closed doors. Not this one.
First, Vinod Khosla quote-tweets Matan calling Factory a "struggling second tier competitor" - which broke everyone’s brain because Khosla Ventures literally led Factory’s last two rounds!
There are levels to FU money, and then there is roasting your own portfolio company on the timeline (unless an analyst forgot to tell him they were in both deals):
Then Sequoia’s Shaun Maguire (backing Factory) steps into the group fight to have his founder's back with this all-timer:
And Samir and Rex Salisbury put together the full mental-pretzel breakdown and RedZone-style map of how every player is connected:
My wife asked me why I was so excited that day, so I sent her this one to explain in laymen’s terms:
One last note - now that Degnan is the top dog @ Cognition, we gotta work on his loafer game. Need him in some deal sleds heading into some of these big-time meetings closing $MM+ deals. These are unacceptable below:
Whaaaat are thoooose!?
Electric day for GTM Twitter.
#3 - Elon’s Dot.com Chess Move & How We’re Using GrokBot
Right after OpenAI hosted their big event and announced their new agent product ("Dots" - which looked identical to Cursor/Grok’s agent ads), Elon Musk went out and bought dots.com / dot.com minutes later and dropped this quote-tweet of Paul Graham:
Elon is unironically the greatest Head of Demand Gen on the planet. He has a dozen companies to run and still finds time to troll his former co-founders for massive distribution.
That got Glenn and me talking about the personal and work agent landscape - specifically Grok Bot, Muse, Instinct, and Devin - and the workflows that are actually saving us hours every week:
The Parent "Polka Dot Day" Hack (Glenn): Glenn runs a multi-agent setup on Grok with a "Chief of Staff" bot managing specialized bots for email, calendar, and random tasks. If you have kids, you know schools send endless emails where buried in paragraph 4 is "Tomorrow is Polka Dot Day" - and if you forget, your kid is crushed. Glenn’s agent reads every school email and texts him and his wife a daily summary of what they actually need to do.
E-Commerce & Promo-Code Arbitrage (Glenn): Glenn hooked Muse up to his credit card to research house slippers, pick a pair, and buy them - with one specific prompt: "If a 20% off popup appears on their website, go through that flow for me because I don't feel like doing it."
Restaurant Reservations, Subscription Audits & Customer Support Wars (Chris):
Italy Trip & Restaurant Arbitrage: My wife and I went to Italy last week, and I had Grok Bot handle all our restaurant reservations via email
There is an arbitrage window right now before restaurants block agent traffic - and for places like Polo Bar where you have to call on the phone, Grok Bot reminded me to just route it through Amex Platinum concierge
Subscription Cancellations: I had Grok Bot scan my expenses across my logins. It found 8 recurring subscriptions, I realized we don't use 3 of them, handed over the encrypted login, and it went out and canceled all 3
Out-waiting Terrible Customer Support: Everyone complains about Eight Sleep or discount travel sites like
super.comhaving brutal customer support. I had a bot camp out on chat and email for two weeks straight escalating a dispute onsuper.comso I didn't have to sit on hold for an hour
Inside OpenRouter’s Sales Org: At OpenRouter, every employee and team has their own internal agents (plus Devin). When new hires start and have a product question, the first thing they do is ask the internal bot - and it hasn't missed yet.
💬 Pro-tip #1: Next time you’re booking a hotel or buying something big, have your agent check which of your credit cards gives the best points multiplier for that merchant AND scrape the web for price arbitrage across booking sites before you check out.
#4 - Paraform’s Talent Density Index & The Elite AI-Native GTM Teams
Shoutout to the team at Paraform, who ran millions of candidate and company data points to publish their Talent Density Index:
Paraform’s index looks at four inputs: funding, school rankings, past employer logos, and general market hype.
From Paraform’s Top 50, I pulled the companies that I know firsthand have truly elite GTM teams (and before any of our Crew portfolio clients come after me in the DMs - I only picked from Paraform’s list and filtered for companies that built out enterprise sales post-ChatGPT):
#5 - GTM Meme Culture
Friends kept texting me that I needed to start mixing memes into the feed, and honestly it’s been a blast.
There is an inverse relationship between how much time you spend on a tweet and how hard it rips. You can spend an hour writing a thread that flops, or fire off a meme on a walk and watch it do 100K+ views.
My inspiration right now is GSElevator and Litquidity - taking the connotations of elitism in tech sales and poking fun at ourselves. A few from this month:
#6 - Why Being an "Order Taker" is Career Nirvana
Being an order taker in sales is the freaking best, and it shouldn't be a dirty word. When someone calls you an order taker, what they’re really saying is that you worked your tail off in diligence and joined a company with an incredible product.
You do not get extra points for playing sales on hard mode.
#7 - OpenAI Sales Attrition & Why "Hunter AE" Roles Should Pay 2x Market Comp
Two more from the timeline that got us going:
1. Leaving OpenAI’s Sales Team to Go Back to Microsoft?
Seeing people leave OpenAI’s sales team to boomerang back to Microsoft, Google, or Stripe threw me for a loop - in my head, if you leave OpenAI, it’s to retire on a beach.
As Glenn pointed out, two things are happening:
first, the 20-hour-a-day AI startup grind isn't a culture fit for everyone from big tech;
second, giants like Microsoft, AWS, and Google are throwing massive packages at folks who have a year of frontier AI credibility to come back and run their AI pods.
2. The "Hunter AE" Comp Trap
If a company wants a 100% cold-outbound "Hunter AE" and isn't paying you way over market comp for it, run the other way.
They’re offloading the hardest part of company-building onto you without paying you for the risk. Too many AI-natives are ripping with inbound right now for good reps to accept that deal.
#8 - Bonus Riffs From the Week: The Circle of Sales Life, AI-Native Tradeoffs & Listen Labs
1. The Circle of Sales Life (Hard Times → Strong Sellers)
You know the proverb: Hard times create strong men → strong men create good times → good times create weak men → weak men create hard times. Here is the GTM version:
Bad products create great sellers → great sellers join order-taker companies → order-taker companies create bad sellers → bad sellers join bad companies.
2. The Real Tradeoffs with the AI-Natives
Brian LaManna had a great post on the realities of startup life vs. enterprise life, and here’s how I frame the tradeoff for candidates every day:
Optimize for max learning, speed, and upside (with risk): Join one of the ~75 Seed-to-Series D AI-natives worth joining right now - just know you’re signing up for 50–60+ hour weeks in SF or NYC.
Optimize for work-life balance, remote flexibility, or family time: Look at Series E+ or established SaaS. Both are great paths - just know what you value before you sign the offer letter.
3. Shoutout to Listen Labs on their $2B acquisition by my alma mater, SFDC
It’s been awesome helping build out their sales team over the past year - truly one of the most talent-dense teams in the game.
Thanks for tuning in!
If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.
For those who are new, my name is Chris Balestras, co-founder & head of talent, media, & brand @ Crew - a GTM recruiting, media, and investing firm, working with seed through series D AI-natives to help them grow.
Where to find Crew:
We work with many of the hottest AI-native startups in various capacities, and for those who are interested, shoot me an email at [email protected] or a DM on LinkedIn.
🫡 cheers,
Chris