Content Library

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

Most companies we work with think they have one ICP. They have six. Six sub-segments hiding under one label. Different triggers, different buying processes, different reasons to care. Then one message goes out to all six. Reply rate comes back low, and the conclusion is always the same. Outbound doesn't work, or the copy is weak. Neither. You ran six tests simultaneously and blended them into one number that means nothing. Maybe one segment replied at 8% and the other five at zero. You would never know. The fix isn't better copy. It's smaller segments, one message each, enough volume per segment to actually read the result. Segmenting feels slower. It's the only version where the data tells you anything. How many ICPs do you actually have? #entreprenuer #startup

One list accepted at nearly 30% last month. Another, same sender, same product, same week, came in under 10%. The difference was where the list came from. The low one was built the way most lists get built. Title filter, company filter, headcount filter, enrich with Clay, find highest fit, etc.... Everyone qualified on paper. Nobody had any reason to know who we were. The high one came off a public conference roster. Same titles. Same company profiles. The only thing that changed is that these people had already put their hand up in public about the thing we do. We benchmark acceptance at 15 to 20%. Filtered cold lists usually land in that space. But lists built from real signal crush that number. Your filters tell you who could care. The signals tell you who already does.

The free pilot feels like the safe move. But it's usually where the deal quietly dies. The pitch makes logical sense. Lower the risk, let the product prove itself, convert later. But free tells the buyer this isn't urgent. No decision date. No budget attached. No one inside who has to stand up and defend the spend. So it drifts to the bottom of the list and stays there. I've seen pilots run for months with no path to paid. Nobody said no. Nobody said yes. The founder kept calling it pipeline. It wasn't. A pilot costs something and it ends on a date. Anything else is just a polite way for them to stall.

To any founder that's selling at prices between $10K and $20K.... Here's the challenge: you're too expensive to put on a card without a conversation. but too cheap to justify paying a sales rep to have the call. So you're stuck. The deal needs real selling, and the price won't fund the person who does the selling. Every deal loses money on the way in and you call it traction. Go lower and make it self-serve. Or go higher and sell it like it's worth what you're charging. The middle is a trap dressed up as a strategy.

I see a lot of demos - and I mean A LOT. Couple key things that I wish more founders understood.... Most demos die in the first five minutes. No shame as a founder in being proud of what you have built, but do NOT 'feature dump' on your prospects. No one is there just to see your fancy UI or your 200 features. You have to do Discovery, you have to identify if there is a problem, you have to quantify the pain, and then you show them how to solve it - simply. Features are 'how'. Nobody buys the 'how' until they want the 'what'.

I'm seeing A LOT of notes in cold invites lately. Here's the thing you have to realize, your LinkedIn profile sells harder than any invite you send. And the headline is the most important line on it. Most founders never touch it. So here's what happens: you send a good invite, they click your profile to decide if you're worth knowing, and your headline reads "CEO @ Company | Helping teams scale | Revenue obsessed." They smell the pitch. They don't accept. You need to be Goldilocks - get the profile 'just right' so you're not coming on too hot (people are good at sniffing out a sales pitch), or too cold (no relevant reason to connect). You gotta show that you're a human who clearly works on their problem. Fix the profile first, then send the invite.

A 9% LinkedIn acceptance rate is not a messaging problem... on a good invite there's no message at all. The best connection requests go out with no note. blank. so when acceptance craters, there's nothing left to blame but WHO you sent it to and your HEADLINE. A low accept rate means you're landing in front of people who glance at your profile and feel nothing. wrong title, wrong company, no reason to care who you are. A blank request is just a person who wants to connect. A noted one is a pitch in disguise, and people are very good at smelling a pitch. Skip the note. Earn the conversation after they accept, not before.

Your outbound isn't getting ignored just because the writing is bad. it's getting ignored because you're selling the same problem ten other people put in their inbox this week. the problem is commoditized. everyone solves "your data is a mess." the gap isn't. the gap is the thing their current tool promised them and quietly never delivered. sell that 𝗴𝗮𝗽 before you worry about anything else.

Here's something you can do right now.... Go read the last 10 cold emails you got. I'll wait. They probably all say the same thing. "Are you struggling with X?" "Is Y a challenge?" Every vendor does this. It's not differentiating you. It's making you sound like literally everyone else. Here's what we changed for a client last month. Same list. Same sender. Same cadence. Rewrote the frame. Instead of leading with the problem, led with value. Give them something that actually helps them improve and identify a gap. "Want me to send you a list of 10 leads that'll be a good fit for you? Want a free video ad I made for you? Want me to send you the audit I ran to show you the gaps in your website?".... etc... Reply rate went from 3% to 11%. Problems are commoditized (especially now with AI). Everyone claims to solve the same one. Do something for them - show them you want to help them, don't just ask "can I get 30 minutes on your calendar", no one wants to meet with you unless they see you can help them.

Jen said something on Lenny's that I love. "I've never in eight years met a founder whose vision was precisely aligned with market reality on day one." We've seen 400+ companies at this point. She's right. It's almost never your day-one target. Had a client go after IT firms for six weeks. Fine meetings. Nobody was rushing to buy. Then a nursing school director jumped on a call and said "this is the biggest problem we have." Completely different vertical. Way more urgent. Budget already there. Three schools in pipeline within two weeks. Founder had never even thought about education. This happens constantly. The real ICP is almost always adjacent to where you started. Different role, different vertical, different use case. Close but not what you drew up on the whiteboard. The ones who find it fast aren't smarter. They just stop forcing it.

enterprise sales is nothing like sales … it’s 1:1 consulting to land and expand $MM deals

founder involvement in enterprise sales is the friggin' magic ... nuance: make sure it's paired in loop with their exec sponsor

90min of enteprise sales talk, you’ve been warned always a blast with you @lennysan 🔥

it’s a corporate liability to not be leveraging this … information/timing edge in policy markets

enterprise sales is game of who can collect the most inside intel surprisingly most don’t OR don't know how to play this game

in enterprise sales: while there might be 5 ‘sales stages’, there’s at least 15 critical steps skip a step and ☠️ yes, corpo is thst sensative to sales process doing a deep dive on this with @lennysan this week

this is enterprise sales /// ‘storytelling is the ultimate compression algorithm for human attention. everything else, data, logic, tech feeds into it, but if you can’t wrap it in a compelling narrative, nobody will give a shit. people think they make decisions based on

if in sales, august is the month to go absolutely crack'd ham

going back for round f’kin’ 3 with the great @lennysan we’ll be digging deeper on enterprise sales … ie winning hearts and minds of Fortune1000 let’s do something really different from other two what is something you want to take away from this session that isn’t well

folks way, way overcomplicate sales they default to this unauthentic mode over trying to cosplay a salesperson over small talk, over question, over write, over pitch, etc. it’s literally the opposite this is why founders are so naturally good at sales, passion is what leads

if you/or company engages in federal or state policy this is absolutely cracked re: information edge identify exactly where to invest, influence and ignore in real-time @StateAffairsUS

in the enterprise, tier-1 logos are the early adopters