Chris Balestras

Co-founder @ Crew ( GTM + AI nerd, blogger ( Springsteen/Joel die hard, miserable Mets/Jets/Knicks fan.

[Chris Balestras @gtmba_]

threw a "selling to developers" event with Clay last week - ~100 top GTM operators in AI

5 takeaways on picking your next breakout opp:
- look for "rabid desire"
- assess the moat
- founder vibe check
- evaluate connective tissue
- NYC GTM talent bar is insane

full breakdown 👇

[Chris Balestras @gtmba_]

A year ago, "I use AI for account research" would've passed the AI fluency check in an interview.

Today that same answer gets scored as unacceptable on the rubric.

The market has moved so fast that the entire fluency framework had to be rebuilt from scratch.

Here's how the new tiers break down:

Unacceptable: you ask ChatGPT questions. Everyone on the planet does this. It tells a hiring manager nothing.

Capable: you've built durable workflows that run on their own. A custom GPT for account research. A repeatable system for a specific use case.

Adaptive: you're chaining multiple tools together. Meeting notes from Granola get fed to an LLM, matched against templates, and pushed as a draft to Outreach or your inbox, with a Slack notification to review before sending. Multiple systems linked with one connected flow.

Transformative: it’s touching every part of your day. You're constantly thinking in terms of what's manual, what can be automated, and how to accelerate outcomes across the board. It's not a standalone workflow, it's your entire operating system.

The real thing being measured isn't technical skill. It's curiosity.

Curious people ask better questions, experiment more, and don't accept the default without questioning it first.

That maps directly to everything that makes a seller effective.

[Chris Balestras @gtmba_]

Hot take: forced culling of the bottom 10% of sellers every year is the McKinsey-era playbook.
Nuance: if your company is ripping and everyone is performing, don't cut the bottom 10% just to cut it.

Look at inputs, energy, effort, and internal brand.
Forced culling makes sense in a non-performing org. not a winning one.
#salesleadership #gtm #cro #enterprisesales

[Chris Balestras @gtmba_]

Over 90% of AI unicorns are headquartered in one city.

If a career in AI is genuinely your top priority, move to San Francisco.

@BardiaShahali mentioned this on our latest pod.

The logic is the same one he applies to everything. Don't make it harder on yourself than it has to be.

If you want finance, you go to New York. If you want acting, you go to LA. If you want to be where AI is actually happening, go to SF.

You can absolutely choose a different city and a different lifestyle. That's a real choice. Just be honest with yourself that if you do, your career isn't your number one priority right now. Which is completely fine for plenty of people.

But the window doesn't stay open forever, and nobody knows how long this wave lasts.

If you're betting your career on AI, the question isn't whether SF is expensive or annoying. It's whether you want to be in the room while it's happening.

[Chris Balestras @gtmba_]

The new reason AEs are taking anthropic isn't comp.
It's risk management.

Reps who used to want to be AE 4 at a hot Series A are parking at Anthropic. They don't know if the app they'd go sell gets cooked by the next Claude release.
not passengers. hedgers.

#aisales #anthropic #aestakes #salesjobs

[Chris Balestras @gtmba_]

@rox_ai 🔥

[Chris Balestras @gtmba_]

@BardiaShahali @meetgranola New Episode with Bardia Shahali is LIVE!

Spotify: https://t.co/WTyUC6q5gL

Apple: https://t.co/ZeokxNRdm2

YouTube: https://t.co/DEfGCoY2lx

[Chris Balestras @gtmba_]

New Crew podcast drop with @BardiaShahali, VP of Sales at @meetgranola.

His career is a clinic in betting early on the right companies:

BlackLine (IPO'd) → Intercom → first sales hire at Teleport (seed to a $1B valuation) → Fireworks AI → now leading sales at Granola.

This one's for sellers plotting their jump into AI, founders building GTM from zero, and anyone trying to pick the right rocket ship before the rest of the market catches on.

Our key takeaways on what most people get wrong about picking a company (and building a team) in the AI era:

1️⃣ A bottoms-up engine isn't a nice-to-have. It's the whole game.

Bardia won't join a company without one. Cursor, Anthropic, OpenAI, Granola: all bottoms-up, all ripping. When users already love the product, your outbound lands warm and you're selling with the wind at your back instead of into it.

2️⃣ AI isn't killing jobs. It's killing the busywork inside them.

Every GTM team he talks to is struggling to hire, not cutting heads. What AI actually kills is the eight-open-tabs outbound grind nobody enjoyed anyway. The reps who win use it to delete the coordination tax, not to phone the job in.

3️⃣ Explosive revenue is no longer proof you built a real company.

$100M ARR used to signal operational maturity. Today an AI company can hit it with janky systems and a tiny team still figuring it out. Hire the exec who "scaled 100 to 500" at a traditional SaaS shop expecting that same structure, and the mismatch washes them out in months.

4️⃣ The steak dinner is mostly dead.

Try to wine and dine a Cursor founder and you'll get laughed out of the room. They don't want dinner. Half the time they don't want a Zoom. For bottoms-up products, in-person still matters (onsites, hackathons), but the steak dinner as a decision-lever is gone.

5️⃣ Founder-market fit is the tell most people skip.

The founders who've actually lived the problem build durable companies. Fireworks came out of PyTorch and had felt every bit of the pain they were solving, so the credibility was automatic on every call. Smart founders just playing with cool tech tend to fizzle.

6️⃣ Hire for mindset. You can teach the rest.

Bardia screens first for optimism and lean-in, the 110% energy of someone who knows this AI window is once-in-a-lifetime. Discovery technique and outbound chops are coachable. Mindset shows up in someone's energy and can't be faked.

7️⃣ The candidates who stand out actually do the work.

Roughly 2 in 100 do more than send an "applied for the role, got 15 minutes?" note. One SDR sent a two-minute Loom mapping how they'd attack Granola's market. In two minutes they knew the company better than almost anyone. That's the bar now.

This one's packed if you're trying to make your move in AI or build a GTM team that survives the pace.

[Chris Balestras @gtmba_]

@evisdrenova They’ve cracked the code and are smart

Easy mode sales

[Chris Balestras @gtmba_]

What if your advisory board never slept, never pulled punches, and had domain expertise in whatever topic you threw at it?

That's the War Council, an AI-powered decision-making tool that @zapier's entire executive team has adopted.

There are standing personas with permanent seats: a ruthless CFO, a wartime operator, a CEO. You feed in your company’s context and the profiles get enriched over time until they're predicting what the actual person would say with something like 80% accuracy.

Then, based on whatever you're stress-testing, the council spins up rotating experts to chime in.

Running an enablement plan? It creates a chief enablement officer from another company and a McKinsey consultant.

The brief is clear: be critical, not nice, and provide real takes.

The final human judgement in decision making will never be replaced, but the War Council can surfaces blind spots faster than any individual advisor ever could.

And it doesn’t hurt that it's available at 11pm on a Tuesday when no one else is too.

[Chris Balestras @gtmba_]

4 risk vectors when hiring senior sellers:
startup risk → can they work with no resources or brand?
technical risk → can they sell something this complex?
deal risk → can they handle your ACV?
culture fit → most people skip this

logos and quota attainment are surface signals. these four are the actual job.

#salesrecruiting #gtm #enterprisesales #salesleadership"

[Chris Balestras @gtmba_]

Most sales interviews are evaluating a candidate’s single snapshot in time.

Where are you right now? What have you closed? What logos do you carry?

The problem is that a snapshot only tells you what someone had access to.

It fails to communicate what they built, how fast they're learning, or what happens when the playbook doesn't exist.

Looking for slope is evaluating them through a different lens entirely.

It's not where they are, it's the direction and speed of movement.

Someone who was doing nothing with AI six months ago and has since built a stack of workflows has a steeper slope than the person with a polished resume who's been flat for three years.

The Moneyball parallel shows up in a real way here.

The Oakland A's didn't have the budget to compete on obvious talent. So they found an edge in attributes nobody else was measuring.

[Chris Balestras @gtmba_]

Most note-taking tools solve the problem by putting a bot in the meeting.

Which works, until you're in a sensitive internal conversation, a candidate interview, or a call with someone who visibly clocks the bot and changes how they talk.

Granola does it differently. No bot joins. It runs quietly in the background, picks up the audio on your end, and by the time the call ends, you have a clean, structured set of notes waiting for you.

We use it for everything at VibeScaling. Internal syncs, candidate calls, client conversations. The quality of the notes is genuinely better than what most people produce manually, and you're actually present in the conversation instead of half-listening while you type.

The use case that sold us completely: calls with people who talk fast and think faster. You stop worrying about capturing everything in real time and just follow the conversation. Granola handles the rest.

Then the workflow is simple. Granola into Claude. Notes become follow-ups, action items, summaries, whatever you need, in about 60 seconds.

It's one of the few tools we'd give up last.

#Granola #AIProductivity #FutureOfWork #MeetingNotes #FounderTools

[Chris Balestras @gtmba_]

Why CROs at hot startups get fired in 12 months:
it's not the CRO. it's the forecast.

founder reverse-engineers the plan from the round they want to raise. bottoms-up math says it doesn't work. plan stays anyway. CRO walks into a number that was never realistic.

accountability needs to land upstream.

#cro #gtm #salesleadership #startups

[Chris Balestras @gtmba_]

Think about the ten best reps you've ever worked with.

How many of them were primarily motivated by money?

If your company is anything like @zapier, then the answer is probably none of them.

That doesn't mean comp doesn't matter.

If you're not making enough money to survive, leaving is a rational decision.

But the input that drives the output for the best of the best isn't the check.

It’s the craft. The long game. Earning the career arc you actually want.

That kind of rep survives bad quarters in stride. A coin-operated mercenary doesn't.

When the numbers dip, the coin-operated person starts shopping immediately.

The purpose-driven person starts diagnosing what broke.

Transactional energy shows up in pipeline reviews, in how people collaborate, in how the team holds together when things get hard.

At the startup stage especially, hiring for values alignment is a non-negotiable.

[Chris Balestras @gtmba_]

The paradox of senior sales hiring:
founders say they want the underdog who won with an inferior product. then they reject every resume from a company they haven't heard of.
Today's "order taker" at cursor or anthropic is tomorrow's most chased candidate. the brand becomes the filter.

#SalesLeadership #SalesHiring #B2BSales #StartupSales

[Chris Balestras @gtmba_]

Everyone wants to join the next Cursor or OpenAI.

But the top-tier investor logos on a deck aren't the full picture.

Roy Mathew breaks down how he actually evaluates early-stage companies (and what most people forget to check):

1. Does this product actually have product-market fit, or just hype?
2. Is there a pathway to durability? Can you see this becoming a company that builds your brand, goes public, and creates a real outcome?
3. Does spend all day with the people excite you? Can you learn from the leaders? Will you be pushed? Do you actually want to be in the room with them?

None of this is rocket science. But people get excited about a company and forget to do the assessment themselves.

[Chris Balestras @gtmba_]

The feedback loop at an early-stage company is the whole point.

Sales tells the product that something isn't landing. Product walks over to engineering. A fix ships next week. That speed is a genuine competitive advantage, and it only happens when everyone is in the same room.

When you're remote, you're on the outside of that loop. You're getting the Slack summary of the conversation that already happened. The context, the energy, the real-time calibration, that's gone.

In sales specifically, it's even more pronounced. The 10 minutes after a call when the team is still in the room is where the best coaching happens. Not the scheduled 1:1.

Not the Zoom debrief. The unstructured, unrepeatable moment when someone who just heard your call tells you exactly what you missed.
Remote kills that entirely.

The best AI-native companies understand this. That's why the ones worth joining have real offices or hubs in SF and NYC.
Not because they're old-fashioned about remote work. Because they know talent density is a compounding asset, and you can't compound it on Zoom.

Yes, this usually comes with longer hours. That's the honest trade-off.
But if you're early in a sales career and trying to grow as fast as possible, being in a room with 10 elite people every day is worth more than the flexibility of working from your apartment.

#Startups #B2BSales #CareerGrowth #ArtificialIntelligence

[Chris Balestras @gtmba_]

The best enterprise rep on your team might be someone who's never sold SaaS before.

One of the reps on @trifamenz's large enterprise sales team is a former startup founder.

He closed about $2M over several years for his own company.

On paper? He’s not a sales background fit.

In practice? Selling from 0 to 1, with no brand, no inbound, no playbook, is one of the hardest things you can do in business.

That skill carries a massive premium that most hiring managers completely miss.

Consultants who've never carried a quota still navigate proposals, build business cases, and win over skeptical buyers.

Hardware salespeople who've sold at depth and show high curiosity aren't far from closing enterprise software deals.

The trap is screening for deal sizes and SaaS tenure when what you actually need is someone who can figure it out.

The Moneyball arbitrage opportunity in sales hiring right now is real.

If you're hiring enterprise reps and your filter starts with "5+ years SaaS experience," you might be screening out the person who would've been your best closer.

[Chris Balestras @gtmba_]

Hiring senior sellers is dating.
Every founder thinks they're the supermodel. Most haven't done the work to attract one.

No pipeline, weak product, off-market comp → you're not getting the rep you think you're getting.
The value of a good recruiter is telling you that early, not after the placement falls apart.

#salesrecruiting #gtm #foundertips #enterprisesales

[Chris Balestras @gtmba_]

@njshoreinvest My nightmare