12 Traits That Make A Hot Sales Job & How To Avoid Joining A Dud

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

You want to join a mafia. 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.

It's the reason everyone wants to work at OpenAI/Anthropic. It's career insurance.

Everybody knows that the next crop of startups will want to recruit from those places. It's like a snowball effect.

If you haven't been in a mafia yet, here's how to proxy it: ask VCs where the smartest people they know are going (see here for how Index saw this with Plaid).

Look at what schools the engineering team attended. Find someone in your network who you think is ridiculously smart. What company are they coming from? The better their former logos, the more options they probably had.

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, and a signal of the company's ability to properly plan GTM capacity. Most of the roles we turn down at vibescaling are because companies want to hire sales too early or overhire, and I won't push that narrative to our network of sellers.

As a seller, you want a tailwind.

I use this analogy often: I’m a miserable Jets fan, and have spent too many hours watching them play the Patriots vs. Tom Brady; we were both in the NFL, but one was clearly a better experience, it was almost like watching a different sport. Don't go join, or be like (or a fan of ) the Jets. Go join a company on easy mode with a shit ton of inbound.

80/20 your decision with #1 and #2. Get these right and you're directionally set up for success.

High growth is getting in at Series A through C.

This is the breakout period: post-product market fit, pre-equity dilution. You ideally want them growing 100% YoY with low-single-digit to ~$20M ARR. You still want upside in deal velocity and pre-IPO equity. The AI natives have somewhat blown up this paradigm, but those ranges are still a good baseline for the bottom end of the sweet spot.

Good lists to proxy off of: Next Play, Prospect, Wing's Enterprise 30, and Exceptional Startups.

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. The way a company structures its margin profile means they'll never pay more than 10-20% for your commissions. So smaller deals, even inbound ones, mean you're still doing all the work (signing paper, back-and-forth, negotiation) for a fraction of the payout vs. the work you did.

$100K deals minimum is what you should be growing into, even if it's not there on day one. It's OK if they're starting in SMB. Just confirm they have a clear plan to move upmarket. Better for earnings and future career growth

Sell in a field that genuinely interests you.

I've learned this the hard way. When I was selling process mining software at Celonis, it was boring AF.

If I didn't care about the problem, it was so much harder to sell. Some people don't care about this and purely optimize for earnings growth, and that's fine. But for me, if the problem doesn't interest me, it's just a grind.

This is a huge reason why everyone is flocking to AI right now too. So interesting to be selling this generational shift.

A lot of people give GTM shit for not being "technical," which pretty much means you never sold to a developer/engineer/CTO. There's almost a "club" that sellers are proud to be in for having sold to devs. We wrote about it more here.

Selling technical products allows you to learn tech deeply and disarms the "not technical enough" objection. If you've only been on the app layer your whole career, you can always flex into the technical sale, but not always the other way around. Companies that sell APIs (think the Stripe sale, the Anthropic sale) will start boxing you out if you don't have those reps.

In 2026, it's still OK to sell on the app layer as long as the product is ripping.

Just get to an AI-native.

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

The benefit of working at a startup is that even if selling doesn't go perfectly, you can accelerate your learnings in ways that compound elsewhere. When I started VibeScaling, part of the reason I was comfortable building a website and testing different marketing channels was because I'd done that at past companies while also selling. That's the startup edge. Fewer resources leads to more projects, which speeds up your learning curve.

It's also just more fun and intellectually stimulating than being the 100th AE at a Series F+ company, selling into 3 zip codes in Michigan.

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

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

A good diligence question: ask them how they got to your quota number. If nobody has a real answer, it's a fugazi number and a red flag.

💬 We just interviewed Jack Gashi at Avoca. Loved how fixated he was on capacity planning and building out the sales org in a modern way. That's the bar you're looking for.

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.

There's a feedback loop that speeds up when you're a team of 10 or 20 and you need to move quick. Sales telling product, product talking to engineering. Doing this in person just speeds up the learning curve, and the faster you are, the better your shot at winning.

Yes, this comes with 9-9-5/6. It's just the cost of doing business right now if you want to be at the best AI-native companies.

A technical founding team that iterates quickly keeps the product relevant and adaptable. Speed is the number one game right now, and every company is fighting for it through hiring and through tools like Cursor to ship more code.

To diligence this: check the changelog vs. competitors. Ask what recent feedback they implemented and how fast. Talk to their customers. If their eyes light up about how fast the team ships, that's your signal. If you get a lukewarm answer, that's a huge bottleneck for you as an AE in deal competes.

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

If they're large enough GTM-wise, see if anyone has recently left and ask them about their experience. Check RepVue - though if they have a robust page, they might already be too big for meaningful upside. Talk to customers directly. Ask: "Is this one of the best products you've ever used?"

One mistake I've made: solely relying on VCs. They’re a good initial signal, but VCs (will explain in #12) are too far removed a lot of times and often don't know how the morale is for GTM specifically.

If they've never been in sales before, what makes a company a great investment does not mean it makes a great job for a seller. Talk to operators, not just investors.

Not every great company has a tier-one VC behind it, but it's a good filter to start with.

Top VCs (Sequoia, Benchmark, Founders Fund, Accel, a16z, Kleiner Perkins, etc.) see every deal. They get pick of the litter. So when they write a check, it's at least a signal that the company cleared a very high bar.

This isn't a perfect proxy. Great companies slip through and mediocre ones get funded by great firms all the time. But when you're evaluating 10 opportunities and trying to triage, backing from a top VC is a reasonable first filter. It's one less thing you have to diligence from scratch.

Start here, then go do the rest of your homework.