We spam “talk to a human” during customer service calls… Why would customer facing agents be any different in B2B?

this was pretty fun

Best thing a hiring manager can do in an interview is tell the rep what's hard about the job. Hardly anyone does. Instead they spend the hour making the rep prove they can sell, which their numbers already told you. Talk about where the team's actually stuck instead. For example: "We close fine once we're in front of the CTO, we just can't get that first meeting booked." Now he knows the real problem you're hiring him to solve. A rep worth hiring wants to know what you’re facing before he takes the job or else he leaves in a matter of months when the going gets tough. That’s why I always tell the managers I work with to say the hard part out loud before they ask the candidate to.

A sales leader stopped me mid-call earlier this year. If the candidate's only edge was sales experience, they didn't want the intro. This was a physical AI company hiring for their next AE. And I've heard the same from other AI-native founders since. What they’re after is a pedigree, work-ethic, and level of intelligence that has likely already been proven and screened for in the fields of consulting and IB. Not to mention their day to day involves a lot of the skill sets and problem solving instincts GTM leaders find desirable. Their thinking is that product knowledge is easy to hand someone. They'd rather take someone sharp and teach them what you sell than take a rep who's only ever sold in one lane. So the ten years in the vertical is not the safe bet that it used to be. These founders are betting the opposite way.

I have such a hard time taking anyone seriously who uses the words moat, wedge, flywheel….. please stop. No one used these words pre-AI.

The best way to pace the frontier is to hold the labs fully liable for the behavior of their models.

A rep will come in wanting way above OTE, and before anyone gets excited I want to know what that number's actually sitting on.  Plenty of them earn it. But a big year and a big year for the right reasons aren't the same thing.  Sometimes the candidate had a loaded territory at a company everyone already knew, and that reads the same on paper as the rep who built it from nothing.  It's really not the same thing once they're somewhere with an empty calendar and no name opening doors for them.  So I ask very early on how they actually hit it. Where the deals came from, or what they'd do if they were starting cold.  Paying up for a real closer is some of the best money you'll spend. But paying that same premium for one lucky year is how you end up with the wrong person.

Besides the score in the top left, this is peak Sunday activity

AI's not going to replace what actually closes deals.  It feels like every conversation eventually gets to AI now. Which tools people are using, which workflows they're building, what's saving them time.  Earlier in my career, I'd just come off a fast-moving startup where we were finding new ways to get in front of people, and I landed at a company where guys had been running the same playbook for ten or twenty years.  I figured I'd walk in and show them a better way.  Didn't take long to realize I was the one who had it wrong.  Turns out the stuff that worked twenty years ago is still true today, because this is a relationship game.

Heading to @unboundevent next week. If you're going or you're in Boston let's link up!

Your worst hire is probably one you made in a bad quarter.  Number's down, the board's on you about it, and that search you had some room on a month ago, now you don't. So you start bending.  You take the candidate who's around instead of the one who's right. Or you swing hard the other way from your last miss and hire the opposite type, and that becomes its own headache.  I see this happen way too often to ignore. Whoever you scramble to hire in Q3 is usually who you're letting go by Q1.  Keep your bar where it was when things were calm.  Hard to do when you're the one getting asked why the number's light. But that panic hire was never going to save the quarter anyway.

The stuff that teaches you how to sell doesn't happen over slack. Remote work, by nature, comes with a filter. The feedback and peer to peer communication will be a bit more buttoned up or polished. In-person always everyone to be a bit looser, more direct, raw. So when I'm digging into a candidate, part of what I'm picking up on is whether they came up around good sellers. They'll talk through a deal differently, they've got instincts you only really get from being around people better than you. I'm not saying remote's bad but if two people have about the same numbers, that feel for a deal going sideways matters to me. And it's not going to be on the resume.

Something I keep running into is a candidate who's clearly great in the interview, and I have to remind the hiring manager that's kind of all it tells you.  They're a rep. Being good in a room is the job, so of course they're polished. They've got a struggle story rehearsed and ready, and they know how to read you and say the thing you want to hear.  Although none of that is fake exactly, it just isn't proof of much either.  You don't find out if someone can sell until they're in the seat and it's month three and nothing's coming easy. That part no interview will show you.  So I've kind of stopped getting too excited about the ones who nail the interview.  Doesn't mean they're not good. I just don't know yet, and neither do they.

Take (not sure if it’s hot or cold): cold call scripts or anything rehearsed for that matter only works on an uneducated or unsophisticated buyer (which is diminishing rapidly). just be a normal human with genuine curiosity, if it’s not there follow up in a few months. some of these viral videos cold calling videos are garbage

Everybody's using AI for their outreach now, so most of it sounds exactly the same.  Which means if you can still write like a person, you actually stand out.  The people who are actually good at this take real pride in how they communicate. And that matters way more than people give it credit for, because it's how a buyer ends up reading your product and reading you.  The second you hand all that off to a tool, there goes the thing that made you different.  Use the tools for a lot of it, sure. I just think the part that sounds like you is worth holding onto. There's less and less of it around.

Biggest thing I picked up running my own company: it really matters what you're selling. Same thing was true back when I was in enterprise sales.  I'd done pharma, software, a few different industries before this, and I never really got good until I was selling my own service in a space I actually cared about.  Everything just got easier after that. There was more behind the conversations, and honestly you end up seeing it in your commission too.  So that's a big thing for me now when I talk to a candidate.  Did they actually look into the company and talk to the founder if they could? Or are they just chasing a title?  You can usually tell because the ones who have done the work want to talk about the product before they ever bring up comp.  And if a sales leader tells me somebody interviewed great but seemed kind of flat on the product itself, I can’t brush that off.  Because when you don't believe in the thing, the hard deals are the first ones you let go.

getting to a point where you’re turning down bad business is such a weird paradox. maturity, awareness, self-respect all come to mind. but at the same time i’m very competitive, and i want to grow this thing as much as possible.

The hiring bar for GTM has shifted, and most haven't caught up. It used to be simple: Quota attainment? Have you sold this deal size to this persona before? Check the boxes, get the interview. But right now, everything/one looks and sounds the same. Same resumes, same bullet points, same career arcs. Hiring managers have noticed, and anyone who looks like everybody else is getting passed over. I'm seeing founders and CEOs calling out the unique backgrounds their people have. A national chess champion. Someone who used to build video games. An Olympic rower. A professional athlete who competed at the highest level before ever stepping into sales. Someone who was exceptional in one area of life tends to bring that same intensity to the next thing they do. What was once "have you done this exact job before" is now "does your experience lead me to believe you can learn quick/offer a new perspective/excel here" We're hyper aware of what AI can do now. Polished doesn't mean unique. The people who stand out as undeniably human, with depth and real stories.. those are the ones getting pulled into conversations. If your resume reads like every other SaaS AE out there, it's time to rethink what you're leading with.

Cold called a CRO this morning and took an L. So I used @perplexity_ai to coach me by sending it the transcript. The feedback was actually spot on: linkedin.com/posts/jake-walb…