One of our biggest competitors went on 20VC/20Sales a few weeks back and I felt compelled to do a solo episode on 17 takes I’m seeing in the AI GTM recruiting landscape in SF/NYC.
Bunch of takes I agreed with of them, and a bunch I didn’t. Hope it’s not too spicy 🙂.
1. "If a rep's been at Salesforce for the last five years, they’ve never opened a new logo + don’t hire them."
Where I land: mostly fair, but it depends.
He's probably right they haven't opened a new logo.
But we assess sales talent on a few risk vectors: startup risk (fewer resources, a company nobody's heard of), technical risk (can they sell something this technical), and deal-size risk (can they sell a deal this big).
The blanket "I'd never hire from Salesforce or ServiceNow" take, the kind of take that folks like Maggie Hott has pushed, misses something.
I worked there, and it was brutally hard to hit number: one of a million reps, a tiny territory, selling into accounts already sick of the four reps before me.
I’d also argue that it was a way harder job than being like AE #5 at Stripe/Slack/OpenAI/Anthropic.
One red flag though: if someone's been at Salesforce five years and is only now eyeing startups, why weren't they dying to leave after year one?
Most of the time it's right to pass on the lifer or person who has been at SFDC a while. But we've placed people who did a year there after three years at a startup and realized the big-company thing wasn't for them - there’s always some nuance.
2. "I have an affinity for not hiring people out of the security space."
Where I land: depends where in security.
What I’ve learned is that a lot of security selling is out of the channel: reselling, selling to someone with influence rather than the business directly. So I get the instinct.
But it depends. The top-tier orgs still running a direct, technical sale to the end buyer, the Chainguards, Wizs, and Snyks, produce great reps. What we get asked for now is usually a top-down sale plus a technical rep, two of the hardest vectors to hire against, so I wouldn't write security off as a whole.
3. "If you're north of $1.5M of productivity per rep in a fast-growing org, keep hiring. Higher and you're leaving money on the table; lower and you're over-hiring."
Where I land: strongly agree.
Love that there's a clean benchmark on this.
If your reps can do $1.5M, the math says you're hiring efficiently and should keep going. We have companies closing $3-4M per rep, which probably means they're leaving money on the table and could add capacity.
The principle is aligning the work and effort with the comp.
I'm stealing this benchmark
4. "If you have to pick your poison on quotas, always set them too low."
Where I land: strongly agree.
Set them slightly too low, not so low people blow them out. Your CAC takes a hit and margins compress, but you readjust later.
Set them too high and you get the spiral: nobody hits number, morale tanks, your A-players leave, the rest get back-channeled out, and word spreads that you don't pay your salespeople. It all comes back to aligning effort with comp.
Seen this play out horribly too many times (happened to me a bunch).
5. "More companies are adding windfall clauses because reps are closing $10-30M deals in three to six months."
Where I land: an interesting learning that I did not know.
Sounds messed up at first, but it makes sense. You don't want to pay $2-4M on a deal that closed mostly because the market's on fire and every exec has a gun to their head about their AI strategy. Even Salesforce added these when I was there, since financial services reps would blow out their number any time a JP Morgan came inbound.
Honestly it's almost a good sign. It means the company thinks deals that big are possible, and even with the clause you're still making a killing.
Just want to align comp with effort, so I get it.
6. "Raising a round doesn't mean it's a good go-to-market opportunity."
Where I land: strongly agree, spot on.
I see a company raise a monster Series B, text my buddy who's an AE there to say congrats, and get back, "I just put in my two weeks, no PMF and nobody's closing anything."
A great business or a big raise does not equal a great sales seat.
This is why it helps to work with recruiters who've actually sold (like us 🙂). We scope it out and give you the good, the bad, and the ugly before you jump.
7. "The best engineers don't want to be forward deployed engineers, and the FDE is just a glorified professional services person."
Where I land: strongly disagree.
Some of the best engineers I've worked with are extroverted and don't want to be at a keyboard all day.
They sit on the technical end of the spectrum but want customer contact without carrying a quota.
Sure, if you're the best engineer on earth, go get $100M at Meta. But plenty of top 5-10% engineers just prefer talking to people.
The other claim, that needing FDEs means your product is weak, I don't buy. We're in the early innings of AI and the last mile to production has real nuance. The FDE getting things over the finish line is critical right now for a lot of startups we work with.
8. "I made too much money, stopped doing the hard things, and needed Chad to kick me in the ass."
Where I land: LOL - this made me chuckle a bit.
This might be the whole reason firms like ours exist. Chad's never been an operator, so it's funny Degnan needed him to come make him eat his vegetables. It's the personal-trainer thing: there's some skill in learning to squat, but 99% of the value is accountability.
The interesting part is how a recruiter and an operator can work in harmony, one bringing the outside push, the other the in-the-weeds context.
9. "Anthropic is offering sums of money the likes of which we've never seen.”
Where I land: agree, its nuts.
We lose candidates to Anthropic every single week. They're still getting sold the inning-one, build-this-to-five-trillion story, and even operators who are usually the "come in at four, take it to twenty" type are now just going. Most don't fully clock that the early-stage product they'd go sell at a Series A or B might get cooked by Claude in the next release.
Add talent density, mostly inbound demand, and top-of-market pay. AEs are around $400K OTE paid as a base salary, so you get it regardless of what you close, plus ~$1M in stock at the current mark.
The "but I want to be a builder" pushback is mostly cope.
Everyone interviews there first, and if they don't get in, they tell the next company they wanted the ground floor. Even as AE 100, that place will have thousands of AEs and you're still building. It's Salesforce in 2001, Stripe in 2015, Anthropic now.
10. "A mistake at Snowflake was slowing down hiring to optimize for going public. We should have kept hiring."
Where I land: interesting, and makes sense.
They pulled back on hiring to clean up margins for the public markets. Meanwhile Databricks inflected and is arguably the bigger player in the data lake space now, riding a huge AI tailwind.
The lesson that stuck: don't slow down hiring purely to optimize EBITDA when you're still in a land grab.
11. "99% of these VCs have never operated."
Where I land: agree.
It's easy for a VC to repeat something from a board meeting or TechCrunch and treat it as gospel, but a huge chunk of them have never carried a bag.
This is why I didn't go into VC straight out of business school. I wanted to operate in a function first for the context.
So much GTM advice from non-operators is why companies over-hire reps and make calls that serve the fund, not the business. They don't care if 19 of 20 fail, they care that one blows out. That's the game, and it's not changing.
12. "Ten years ago I could sell a candidate on joining a John McMahon company. That's a much harder pitch today."
Where I land: found this to be super interesting, but I will say a lot of reps want to be coached by the MongoDB tree.
Anthropic has basically every piece you'd want in an enterprise sales role, so until it shakes out, this dynamic holds. Top reps grab the brand halo and talent density, then roll to the next big thing.
For now it's a trickle-down: did you get into Anthropic? If not, you play in the other still-great roles, which are the ones we recruit for - hit us up.
13. "Every healthy sales org should be trimming the bottom 10% every year."
Where I land: disagree.
This is the McKinsey, stack-ranking view of performance management, the same thing that got toxic at Enron. It runs on fear.
If your sales org is genuinely crushing, someone landing in the bottom 10% doesn't automatically get cut. Look at inputs, energy, effort, and internal brand first. In a non-performing org, sure, you trim. But you don't cut 10% just to cut it when everyone's winning.
14. "Everyone is working a shit ton right now. I'm at 70 hours a week.”
Where I land: strongly agree.
Everyone's working more in the AI era than the SaaS era. Speed is the moat, so there's more to execute on. And the only way to stay enabled now happens on nights and weekends: Twitter, vibe coding, tinkering with tools, trading notes with peers on how they actually use AI.
So you're working more than ever and still learning the leverage points off the clock, and weirdly everyone feels energized about it. Biggest paradigm shift since the iPhone, probably bigger, and people are grateful to be in it.
15. "AI native startups are handing out $100M CRO packages."
Where I land: wild, and a sign of how bifurcated this is.
We're getting into exec search ourselves now, mostly founding sales leader and VP roles. I haven't seen nine-figure packages at Series A or B, but for a Brian McCarthy at Cursor, or a CRO at Anthropic or xAI, I get it. As insane as it sounds, that's still only about 1% of a company at these valuations.
It's the K-shaped thing: either you're at one of the top 40 companies or it's a grind/painfully hard mode. The top 5% are benefiting like never before, and everyone else is watching from the sidelines or feeling the anxiety of trying to get in.
16. "Seat-based pricing is dying and everyone is baking consumption into their model."
Where I land: agree, this is clearly the future.
I was the fourth or fifth AE at Metronome, so this one's close to home. A lot of these AI-natives carry their variable cost on the back of LLM tokens, and consumption pricing passes that through, a cost-plus margin profile. For anyone who's sold PLG or usage-based, this is familiar.
If you're the "sell the $10M deal and walk away" type, you’re worse off (I’d argue that you weren’t a great seller to begin with). If you'd rather people pay only when they're getting value, it's a step in the right direction.
17. "I never look at industry experience. What matters is the quality of the sales org you came up in."
Where I land: strongly agree.
We constantly get inbound like, we're an AI-native ERP company, find me someone who's sold ERP. The problem is those reps usually aren't modern sellers. A lot of them don't live in cities anymore and won't be in office five days a week. Hire someone genuinely smart and they'll learn your ICP and buyer. The one exception is selling to developers or a technical audience, where that does need to line up.
Industry expertise is overrated, and even more so when people are really just buying a Rolodex.
Thanks for tuning in!
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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