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You have to be specific about what your AI does, or buyers lump you in with a thousand other companies. Enterprises only have budget for AI right now. So everyone is pitching an AI solution, AI company or not. "AI governance" or "operational efficiency through AI" sounds good on paper. It doesn't tell the buyer anything. Name one use case they already feel. Who has the pain, what it is, how you fix it. An AI governance client found companies running one big AI search tool and wrote: "I'm seeing this is a problem in your search tool around permissions. Is this something you're aware of?" No mention of governance. Just a problem they could check that day.

If they will not pay for the pilot, they were not going to buy the product. A small fee is not about the cash. It is the filter. Budget, a date, and someone inside who owns the outcome. Skip that and you get logos with no path to paid. Usage without a decision. A calendar that never forces a yes or a no. Put the price and the end date on the table before the pilot starts. That is when you find out who is real.

Enterprise sales is not a speedboat. It is an ocean liner. You can change the intro call, the demo, or another piece of the process this week. You will not know if that change, or the system around it, is working until many deals run the full cycle. You may know anecdotally earlier. The opener lands. The demo stops wandering. Buyers ask better questions. That is still not the scoreboard. It does not show up in the numbers until deals go all the way through. The rest of the cycle has to finish with that change in place. One closed deal is a hint. A run of finished cycles is the proof. That takes time to come to fruition.

People buy because you understand their problems, not because your product has great features. Most founders start at the demo. That is where they get in trouble. A demo is a tour. The sale starts earlier: the job, the felt pain, what they already tried. The product comes in after that, and only the slice that answers the pain you just heard. If the buyer cannot repeat the pain back before you share a screen, you do not have a deal. You have a tour.

The biggest problem we see with AI startups isn't the tech. It's that the person who'd actually have to use the thing doesn't want it to work. The exec loves your demo. That person kills the deal, and you'll never hear why. Here's why. They heard AI and heard "you're training your replacement." No demo fixes that. What fixes it is making that person the winner. Not "this does your job for you." More like "this takes the worst part of your week off your plate and makes you look good doing it." The exec is deciding whether it works. The person under them is deciding what happens to them. Almost nobody sells to the second one. That's the deal you're losing.

Gong Labs looked at 7 million sales opportunities this year. Quota attainment fell from 52% to 46%. Not because reps are closing worse. Because they're working fewer of them. That's a targeting problem wearing a volume problem's costume. Most founders think they're testing one or two ideal customer profiles. They're actually running a dozen sub-segments through the same message. A low reply rate isn't proof outbound is broken. It's a blended average of a dozen tests, and some were probably fine. Stop cutting your ICP by vertical. Cut it by who owns the problem, or by who's already showing intent. The same job title feeling the same pain generalizes better than an industry label. If your entire market is 40 logos, cold outbound isn't a copy problem. It's the wrong motion. Count your ICPs honestly. You probably have twelve.

Salesforce just gave its AI agent a memory that spans months, not single tasks. The zero-to-one problem didn't move. It solves who runs the motion. It does nothing for what the motion is. A senior sales hire and this agent fail the same way: both scale a motion that already exists. Neither can invent one. Finding your 10 to 12 buyers, the message that lands, the medium that reaches them, is still a founder's job. No headcount line does it for you, human or synthetic. Before you pilot it, ask the question that was always the real one. Do you know what repeatable looks like for your business yet? If not, the agent just helps you fail faster, with better project management attached.

The US sales leader you want will not join an unproven motion. That is why the seat keeps turning over. The person you want is already doing well somewhere else. The first thing a good one asks is what is repeatable here. If the answer is nothing yet, they pass. Or you settle, and they leave in eight months. You cannot hire someone to invent a motion. That is a different job than running one. Prove it first, even crudely. Then hire someone to run a playbook that already works. A new market is a zero to one problem wearing a growth stage costume.

Everyone chases product market fit. Almost nobody checks whether anyone cares about the problem first. Two tests, usually run in the wrong order. Does the problem hurt enough that someone will pay to fix it. Then, does your product fix it better than what they do today. Red teaming against AI personas. Six handwritten notes. Colleagues saying it sounds cool. That is simulation, not validation. Of 249 YC go to market startups since 2023, about 2% still pitch full SDR replacement. Those demoed beautifully too. Stop asking buyers if they have the problem. Ask how they handle it today. The gap between what they say and what they do is the finding.

If every deal you closed came from someone who already knew you, that is not traction. That is a ceiling with a nice view. Warm buyers grade you on trust. They take the meeting because of who asked, which tells you nothing about whether the problem is real. The network runs dry right when the next round depends on growth. And the bar moved. Over half of seed and Series A dollars this year went to rounds of 100 million and up, and Series A now expects revenue where it used to accept a story. Warm pipeline proves people like you. Cold proves the problem is real. Warm gets you to seed. Cold gets you to your A.

Our Co-Founder Jen Abel back at it again with Lenny Rachitsky offering absolute gems for enterprise sales. Highly recommend giving the full episode a listen. The ROI is there!

Nobody booking meetings is a symptom. Not the cause. It could be messaging. It could be infrastructure, deliverability quietly collapsing underneath you. It could be that problem solution fit isn't there for this market right now. Four different problems, four different fixes, and volume solves none of them. The sharpest question I have heard a sales leader ask about his own team: is the playbook not working, or is the playbook not being followed? He could not answer it. That was the actual problem. Watch what happens when the rep cannot answer it either. They miss a number, drop the cadence, chase whatever channel looks hot that week, then crank volume to compensate. Bounce rates climb. Sender reputation goes with them. The harder they push, the deeper it goes. None of that is a rep problem. It is a diagnosis problem. Before you add volume, work out which of the four you actually have. #entrepreneur #startup

my favorite activity in the world is introducing corporate execs to one another via text the S-tier aspect of ent. sales

enterprise maturity arc with AI = Dunning–Kruger Stage 1: building with agent’s internally Stage 2: a lot f*kin’ harder than we thought Stage 3: take our $$$, here’s what we want; let’s go

80%+ of my sales activity (async chatter) is in texts seldom email

if in enterprise sales welcome to the 3-month stretch in the pain cave

i can’t tell you how overcomplicated people make sales proof: non-sales folks often with out-perform traditional sales people

sales folks your entire job is to not look like OR act like sales … it’s to cos-play the founder market should feel energy, passion, and trust through you

my cheat code this year 3 days a week, 1-hr virtual training with Molly Lauridsen a total jolt and unlock to system my focus: core & functional work way more intense than Peloton she’s based in Stowe, VT for in-person OR 1:1 virtual sessions best investment to stay

in enterprise sales the more excitement they show on first call; the more a red flag real, real opportunities play it cool

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

the less time I spend on email; the higher the response/reply rate

it happens slowly and then all at once … markets rapidly adjust

enterprise sales is: 20% -- rizz 80% -- reading in-between the lines, collecting nuanced insider intel, co-authoring, and improv re: storyline/frame the biggest mistake is is when folks hire expecting rizz to be 80% of the craft