11 Tips to Ensure Your Next GTM Opp in AI is the Right One

In our first series of in-person events (see video of event 1 and video of event 2) - we had these topics generally around “GTM + AI - selling in the AI era.”

While these were great (many more to come!), one thing we kept getting asked was:

“Can you go deeper on the topic around choosing the right company and what questions to ask/what to look for?”

We took this feedback and threw a recruiting event around this exact topic with one of our hotter portfolio companies, Pylon (shoutout to the recent Enterprise Tech 30 and IA40 lands - well deserved).

See video below for an overview of the event:

This article is a remix/mash-up of a past article earlier in the GTMBA journey, “11 traits that make a sales job desirable.”

The bottom line is that sales is hard, but it’s not a complicated profession.

Yes, be good at your craft. As good as you can be.

But what matters more, WAY more - is joining the right ship.

Bad seller, right ship? Seller crushes quota.

Great seller, bad ship? Seller misses quota.

One matters way more than the other (even though you should be maximizing both).

See below for a list of 11 things you should be checking to ensure that you are joining the right ship (obv all of these are tough to hit, but get your score as high as possible to de-risk):

1. Join A Mafia / Talent Vortex

This is the most crucial factor to consider when evaluating a company you want to join. Hands down.

You want to join a mafia - see here for a deep dive we did a few weeks back with the current / previous ones.

Smart, hard-working colleagues will inspire you when you're working with them (which will make you better) and will also pull you to the next companies they join. People get their next jobs from referrals and former colleagues vouching for them internally, so focusing on this flywheel earlier in your career will pay off dividends later.

Sam Altman agrees with me here, and it's the reason everyone wants to work at OpenAI/Anthropic. Find your talent vortex.

2. There Should Be Clear Signs Of Market Pull

This could be inbound lead flow, or outbound meetings just feeling easier to book because it’s clear the problem statement resonates with your ICP.

A strong inbound flow indicates a strong market pull, more enjoyable work (as you'll be closing rather than sourcing), and a signal of the company's ability to properly plan GTM capacity (more demand for the product than salespeople hired).

Most of the roles we turn down at VibeScaling are because companies want to hire sales too early/overhire for sales, and I won’t push that narrative to our network of sellers.

3. Find The Right Risk-Reward Sweet Spot - IMO, Series A thru D

High growth is getting in at series A --> D (although this depends on the company, I'd still recommend you go to Anthropic even though they're in a later stage). They're ideally growing 100% YoY and already have a few mil ARR-10M in ARR (to show that they already have PMF), and you want to join them in that XM --> 100M ARR journey.

This allows you to hit a period of arbitrage, where you are most likely past product-market fit but have the upside in deal velocity and pre-IPO equity.

Aka, the breakout period:

It's been well documented on this, and see below for some good lists here:

• Why Join A Breakout

• Exceptional Startups List

• Next Play

• Prospect

• Wing’s Enterprise 30 List

4. Make Sure The Product Has A Path To The Enterprise / Large Deals

The product might have a strong PLG motion with inbound, but can it scale to the enterprise?

Selling big deals is how you make a ton of money in GTM and is a highly marketable skill that companies want to hire you for. Ensure that the company shows a signal that they can go up-market in a repeatable fashion.

It’s OK if they don’t have that just yet - a lot of companies start out in SMB. But ask them questions around their plans to move upmarket.

5. The Industry / Problem You Are Solving For Must Interest You

Sell in a field that genuinely interests you.

This might seem obvious, but I've seen the top performers align to products and industries that they are extremely interested in—it makes them better sellers.

This is a huge reason why everyone is flocking to AI right now rather than wanting to sell salon CRMs or another HR tech tool.

6. Sell Complex Products

A lot of people give GTM shit for not being "technical," - which pretty much means you never sold to a developer/engineer/CTO, or they don't think you have the intellectual horsepower to figure it out.

There is almost this "club" that people are proud to be in for having sold to devs before - wrote about this here in detail in a past GTMBA article.

Selling technical products allows you to learn tech deeply and disarms the "not technical enough" objection, which will make any cerebral seller mad.

The smartest and most talented people in GTM sell technical products (think Stripe, OpenAI, etc.).

However, this is changing in the AI-era, as a lot of sellers (who are technical) are going to the app-layer in AI because of the boom we’re seeing with tools like Harvey, Decagon, and others.

Technical products are stickier and usually have a PLG motion, which is generally easier to sell. There is a paradox here, as the smartest people in tech go into situations that allow them to be successful in easier sales environments (aka PLG).

Pretty much, in 2025 it’s ok to sell on the app later as long as the product is ripping - all of these AI products have enough complexity to them to prospects (who have no idea how to buy/use it).

Bottom line - just get to an AI-native, whether technical sale or not.

7. Ability To Do Other Things In GTM (Besides Selling)

Smaller companies allow you to contribute beyond sales, enriching your experience in marketing, strategy, product feedback, or operations. This broadens your skill set and makes you more valuable within (and outside) the organization.

It's also just more fun and intellectually stimulating than being the 100th AE at a Series F company, where you only sell into 3 zip codes in Michigan. Top performers I've spoken to want more than just doing that. They despise big companies because of this

Smaller companies naturally will give you this opportunity despite having fewer resources - just make sure to confirm this (if it’s of interest - this is very much a nice to have a subjective based on the seller profile).

8. The Sales Leadership Must Be AI-Native / Not Dinosaurs

Work for leaders who are cerebral, modern sellers (who adopt and use tools like Clay). They see sales as more of a science (using data) than an art (schmoozing over a steak dinner). They come from banking/consulting/startup/elite academic backgrounds and are thoughtful builders.

Don't work for old-school, crusty sales leaders from Jurassic SaaS companies like Oracle/PTC/Outreach/etc. The ones who offer expiring month-end discounts to create urgency, the ones who ask, "How does this affect you personally?" and the ones who use fear to motivate their sales team rather than create a thriving GTM environment for top performers to be attracted to them.

9. Work At Companies That Have An SF/NYC Presence

The best companies recognize the talent density of NYC and SF, and they foster offices/hubs in these cities. Top performers want to be near other top performers in person, so look for companies that understand this.

And yes, this comes wiht 9-9-5/6 - it’s just the cost of doing business right now if you want opportunity

10. The Engineering/Technical Team Needs To Always Be Shipping

A technical founding team that iterates quickly keeps the product relevant and adaptable. Fast shipping helps the product stay competitive and promptly addresses customer needs, which is crucial in competitive markets or technology with a mediocre moat (which is more common now with software being easier to spin up than ever). To assess this, check the company's changelog vs. its competitors.

11. Backchannel the heck out of everything

They are backchanneling you, you need to be doing the same.

If they are large enough (GTM-wise) - see if anyone has left the company and ask them their experience & if it tracks what the team told you.

For quota attainment, these smaller companies might have a GTM team that is too small to have a RepVue ranking. If they have a robust RepVue review page, they're probably already too big for you to capture meaningful upside.

If no prior reps (you are joining early) - our panelists mentioned that they would ask VCs or just other smart people in their network they deeply trust (who have had wins before).

For those who are new here, my name is Chris Balestras and I run a GTM advisory and recruiting firm called VibeScaling. We help seed thru series C startups place high-slope GTM talent.

Shoot me a note if 1) you are an AI-native looking to hire GTM (AE/BDR/SDR) talent or 2) a candidate on the market and want to be plugged into our selective portfolio of startups for these roles.

Through GTMBA (our content/community arm), which I write with Julian Sheinbaum (top rep @ Windsurf/Cognition) we write about the intersection of GTM + AI + startups, while throwing private events in SF/NYC once a month.

Shoot me a DM or reply to this if you want to be considered for our next one.

See you all next week 🫡,

Chris