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Are you a startup founder who can build a product but lacks the confidence to go out & sell it?
Are you afraid to "bother" potential customers & fail when you do get a chance to talk to them?
Or you simply don't know where to start with B2B sales?
I have your solution...
👇
I can tell you with full confidence, many SF founders will only hire from certain colleges
Nah. Top AEs who have bdr support are still making cold calls to break into accounts and target the higher value prospects.
Even good AEs and most sales leadership who don’t have to make calls tend to be above average at cold calling.
How come a company hasn't been able to disrupt Fanatics? Do they have a moat with long term licensing deals?
Short term, great. Long term, not great.
Very bad for entry level workers.
Looking for remote work when you’re not a great candidate, which is most people, is also a major negative.
You gotta pay a lot more
You can’t build “elite teams” and “in the most competitive space” with the promise of equity and below market pay.
If you’ve interviewed dozens, you can’t find what you want yet so the best lever to pull is comp.
Elite talent gets offered equity and good comp.
Setting that range to 60k a year at the low end will push away most legit people too. Anyone with a little startup experience is always skeptical of the promise of equity over salary. And if you’re elite you can get both.
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Agree. We’ve had clients who want ai literacy. It’s very hard to find.
Everyone lies or exaggerates.
Easy test is to ask what they’ve built. They’ll almost always pivot to describing how they use ChatGPT or Claude to help write emails or prepare for a sales call. You can tell they’re not serious. It’s not the best and final way to test for literacy but you need to be hands on.
"What problem is a priority for you to solve right now?" is how you get the insight needed
The key here being priority.
And then you can ask, what have you tried? Why didn't it work?
really good post
One of the most important things to understand about startups is that because they grow intensely fast, they tend to induce a lot of anxiety in their founders due to perceived lack of control, and this anxiety manifests itself in various ways.
A classic one is in projects that amount to ways to achieve greater legibility - hiring people to build dashboards, 'processes' to 'get their systems in order'. Almost always this is not actually addressing the real problem, which is inevitably a people problem.
A perennial one is problems with sales discipline. Most salespeople are by nature crafty, ambitious, lazy, and somewhat bad with tech. They want to be on calls yapping all day and will do the bare minimum of admin that's tolerated by the business.
As a result, most businesses have CRMs with terrible data quality. This results in the hiring of RevOps people, data engineers, more recently 'GTM engineers', etc. But it's fundamentally not a data problem. The problem is that the sales reps lack discipline and accountability.
The founders or execs will convince themselves that if they can just get the perfect system in place with the right dashboards and fields, if they just figure out how to dedupe the data just right and build the right context layer, they'll be fine.
But it's bullshit. They're avoiding the real solution, which is that they need to fire their underperforming reps and tell the rest of them that if they don't have their hygiene on point by the end of the month, they'll be fired too.
In the past this was a hard ask to make because CRMs were legitimately terrible and updating them took a long time. But this is no longer the case. If you give every rep a Grok Bot, keeping the CRM updated is trivially easy.
This is what actually effective AI transformation in GTM looks like, btw. Anyone who is leading with the tech is selling you a bullshit snake oil solution that will be tech debt in a few months. The real opportunity is in raising standards, driving massive amounts of urgency, and then using the new tech to find resourceful solutions to these new demands. Otherwise you'll just spin your wheels and build some pointless science projects
Exact pattern matching is why hiring managers spend too much time interviewing and more importantly, why you’re missing out on good talent.
You don’t need moats to make money.
Moats are a legacy concept from VCs to find a reason to not invest in your startup.
One counter to this is seeing all the ai slop graphics being publicly created by businesses.
If that’s what they’re sharing publicly to try to get customers, imagine how bad the software they’re creating is.
I have no doubt software is in a tough spot but most businesses can’t even do the basics correctly.
You move to NYC or SF if you want to get into tech sales. You can afford both cities as an SDR/BDR.
You get roommates, you focus on jobs 5 days a week in office, and then you have remote options in two or three years. Then you can live anywhere and optimize for cost of living and taxes.
Most likely you won’t leave either city.
One of the hardest hires to make, imo.
They usually start their own company.
The people who are this good are usually earlier in their career, typically non traditional backgrounds and have already made money online.
Just not a common profile. Former founders with marketing background can sometimes be a good starting point.
Tech people don't understand the appeal of the "treasure hunt" for a lot of shoppers
So many candidates try to pitch their previous company rebrands as them now having ai experience. Dishonest and misleading all around.
Overlooked sales tip:
Be gracious when you don’t win your prospect’s business. Always reply when they say they’re going in a different direction. Wish them well and thank them for their time.
I’ve had two new prospects who went in a diffrent direction 60 and 300+ days ago, come back and sign.
(You also need to provide a good sales experience so they remember you)
This is why meeting in person is critical. You’ll get all sorts of side chats. Sometimes the convo you have walking to the elevator will be the most important one. Getting lunch or drinks can be huge too.
one of the best enterprise sales lessons we learned after YC was working the room between meetings
early on I’d run a discovery call, bring a bigger group to the demo, then ask about next steps and hear something like “we’ll discuss internally”
that’s one of the worst answers you can get because there’s nothing to do but wait
the thing we eventually learned was that deals don’t close on the group call, they close between them
once we started building separate relationships with each stakeholder in the deal (not just the champion) a lot of the guesswork disappeared
between meetings I’d reach out individually and ask something like “how’s the team feeling about everything?”
I had no idea this would work. people started telling me all the objections in the deal, who was raising them, and what we’d need to do to move the deal forward
then we’d walk into the next call and spend time recapping everything we’d already addressed in our 1:1s
once we began doing this, we started hearing a lot less "we'll get back to you" and a lot more "let's loop in legal to start contract review"
it sounds super obvious, but you can eliminate uncertainty in any deal by just asking the other person on the other side of the table what they need you to do, and then doing it
I’ve always thought companies should offer weekend interviews, but I’m sure a lot of candidates will complain that companies want them to use their weekends to interview.
We have conducted interviews on the weekends but the no show rate is very high.



















