Isaiah Crossman

@natolisnuggets lol

P Club winning AE negotiating their comp

@LindySalesGuy @pipelineclub100 Maybe

@IsaiahCrossman @pipelineclub100 It would be wallet-stimulating, lol

FYI to my followers. Anthropic has a load of AE roles open. If you don’t mind in-office in NY or SF, should at least try. Generational wealth opportunity on that team.

@pipelineclub100 lol fair enough

@IsaiahCrossman I wouldn’t complain. I’ve got plenty of other intellectually stimulating projections to balance with the cash

Founders, if a world class salesperson costs X in NYC or SF, they also cost X to hire remote. There's no discount for hiring remote at the top end of the talent curve. There are enough sick remote roles that they can live wherever they want and make a ton. If you want them, you have to pay.

@RooktoRep If your customer is picking up on any sort of verbal pattern like this, it's a mistake. This is one of those things that's actually easy to have Claude coach you on just by asking it to review a few transcripts.

I was on a disco call the other day with an AE… Every other line was: “It sounds like…” “So if I’m hearing you correctly…” aka label + mirror on repeat. Here’s my take: Chris Voss made it popular, but now it’s too popular. Even buyers know the playbook. Suggestion: labels & mirrors are great, just reword it and make it your own

If you're trying to hire good salespeople and the first step of your interview process is having them talk to an AI interviewer, you're basically guaranteeing that anyone you hire is not in the top 25% of talented candidates.

I haven't actually tried what I'm about to suggest so grain of salt lol , but: there are claude skills you can copy called "humanizers" that remove all of the AI tells from your writing. Was reading something for a client the other day that was SUPER AI coded and suggested this. Worked really well for him.

When a prospect opens an email in 2026, they quickly scan it to answer one question - is this AI slop... or was this written for me? It's much harder to tell with short emails and less characters if it was manual vs. automated. For automated emails, you want to keep them as short as possible. I created a new concept I tested out in 2025 to great success: "𝗣𝗲𝗿𝘀𝗼𝗻𝗮-𝗹𝗶𝘇𝗲𝗱" 𝗲𝗺𝗮𝗶𝗹𝘀. These are email templates you create that require zero manual updates before sending and will be automated. However, they seem like they are personalized, written by a human, and not sent via automation because they are very relevant to a specific persona. Here are the different types of "Persona-lized emails" I create: -Social Proof -Short Video -Images -Memes It will take you 2-3 hours to invest the time to build out strong touch points for all 4 personas, across these options. Remember: It's worth the time investment for you. Because other sellers aren't willing to do it.

This kind of thing actually works. And there's a great broad sales mindset lesson here. If your product is actually valuable to the customer and they express interest in it, it's actually BAD to be unnecessarily hard to buy from... For example, calling the person right away (as long as you nail the tone, which I'll describe below) is genuinely helpful. Why add layers of back-and-forth emails when you can leap forward 5 steps with a 4 minute call? Now the customer is WAY closer to solving their problem (truly good for them). Now as for tone, you gotta be very careful. If you call up with a salesy vibe/commission breath, you're prob doing more harm than good. You want to be super neutral. Almost like monotone, as if this is the most run of the mill thing you've done today. And have a helpful vibe. "Heyy Bill -- saw your note and figured I'd just give you a quick call. I'm kind of a phone person. Do you have 2 minutes quickly now and then we can figure out next steps?" Neuuuuutral tone.

I once got a signature on a $1,000,000 ARR deal the last day of Q2... The next business day, right after July 4th holiday, the company fired half the c-suite. Deal would have been totally f'd if it hadn't been signed 1 "day" earlier... So I agree 100% (for enterprise sales), BUT I don't think it's realllllly because of perception... By the time you get to the signature process in enterprise, the decision about whether you're reputable or not has already been made... Nobody in the signature process is going to kill the deal because they don't like your choice of saas tool (though I guess it's possible for some truly obscure open source thing like you're saying, but pandadoc or whatever is fine, even if a little cringe lol). The issue is lack of familiarity... If the procurement person doesn't know how to easily forward it... If the signer can't find it in their inbox by searching "Docusign"... You run the very real risk of adding days to the timeline... And as they say... "time kills all deals"

@boardyai Attainment

Pitch me your company in 1 word.

@dave_christison lol, but actually

your Enterprise AE who hasn’t missed in 6.5 years dialing into forecast call camera off “nothing from my side”

There’s actually a very valuable lesson here if you’re hiring salespeople… The best reps at random companies are ALWAYS stars. People who sold Zoom in ‘21 though…

@natolisnuggets We’d both hope it goes without saying lololol but reality is mannnnnny reps just read the questions verbatim and then just get rolled over by the customer. Handle w care.

@IsaiahCrossman Yeah def can’t come off as or be a rude or a douche But that goes without saying here

Sales reps: you can't be afraid of friction in your deals and you can't be a 'yes' man or woman with prospects. You need to be able to challenge them & stand your ground. Here are a few softening statements to accomplish this: 1. Is it okay if I challenge you on that? 2. Can I ask a potentially uncomfortable question? 3. Mind if I pushback on that? 4. Mind if I share a different perspective? 5. I guess I am a little confused, you mentioned X but what I am hearing is Y.. Can you help me understand how... 6. You probably already thought about this, but… 7. How would your CEO react if.. 8. Keep me honest but... 9. Doesn't seem like this is a fit -- maybe I am wrong? You're not being rude at all. You are preparing them for a tough question or challenge statement in order to understand the true 'why' It does both of you no good to just nod and agree.. No friction no deal.

My first sales manager told me to get really good at asking questions so I went and listened to tons of podcast interviews, specifically focused on what (and almost more importantly… HOW) the interviewers asked. I was just reminded as I was doing the dishes and listening to a Tim Ferriss interview… perfect example. He’s just so curious. And so clearly seeking real understanding. Digs in when he doesn’t get what he’s looking for. Moves to something new and interesting when he’s exhausted the topic. And he keeps the interviewee (think: your customer) super engaged. Try.

@jjen_abel A silly "qualification framework" that for salespeople who have no business acumen.

@IsaiahCrossman what’s BANT?

only three things matter in enterprise sales … 1. is there internal pressure/incentive 2. do you have their cell number 3. have they shared insider intel/gossip

@Chris_Orlob This is THE key to selling anything expensive in b2b. Doesn't matter if it's what you lead with in the sale OR if it's "JUST" justification to help the champion get approval to solve a thorny problem. It's required if you want to sell anything expensive.

"I am not a salesperson. I am a business person who happens to sell." Most reps can explain their product. The top 1% can explain how it affects revenue, margin, and payback period. Buyers don't buy products. They buy business outcomes. Learn to speak that language.

Yeah, there's a lot of talk that "generic cold email is dead" thanks to AI. And I guess to some extent it's possible that's true? But I still see example after example after example of effective well written *relevant* cold messages that happen to land in the prospect's inbox at the right time (when they are actively interested in solving the problem you solve).

there are many games you can play to make money but if you're not making money yet or losing sleep over where your next customer will come from there's only one game you should play: the numbers game I hate cold email and yet am oddly inspired by it because it's a good reminder: whatever it is you're doing, there is always a volume at which it is statistically impossible to not make money