How to close $100K+ enterprise deals, step by step | Jen Abel artwork

How to close $100K+ enterprise deals, step by step | Jen Abel

Lenny's Podcast: Product | Career | Growth

August 23, 2026

Jen Abel is the co-founder of JJellyfish and GM of enterprise sales at State Affairs. She is widely regarded as one of the sharpest practitioners in enterprise sales, and for that reason, this is her third visit to the podcast.
Speakers: Lenny Rachitsky, Jen Abel

Topics: Technology, Business, Entrepreneurship

**Lenny Rachitsky** (0:00)
So we're gonna do something really unique with this conversation. Basically go through the enterprise sales lifecycle, step by step. Let's set this up.

**Jen Abel** (0:08)
Let's start with how do I even get the first meeting? We're in this flood the zone moment of everyone trying to break into the enterprise. But like, what exactly are you solving for them as a problem that's level one, but most importantly, the alpha? And it needs to be different.

**Lenny Rachitsky** (0:22)
Step two is basically running the intro call.

**Jen Abel** (0:24)
This is the most important call out of all of them. This is what I like to do. Super informal, don't show them a demo, don't show them slides, focus on them, have a one-on-one dialogue for 30 minutes. The whole game is to slow down to go fast. And by the way, do not bring a recorder to this call.

**Lenny Rachitsky** (0:45)
What are the benchmarks for how often you get through each of these stages?

**Jen Abel** (0:48)
The win rate for enterprise is usually around 30 to 35%. If your win rate is higher than that, your price is too low.

**Lenny Rachitsky** (0:55)
What are some signs that your salesperson is not doing a great job?

**Jen Abel** (0:59)
Most successful salespeople are not trained salespeople. The fastest way to commoditize yourself is to go into some sales script. Budget, authority, need, timing, that should be in the back of your brain. You never actually ask those questions.

**Lenny Rachitsky** (1:09)
What percentage do you think are just doing it wrong?

**Jen Abel** (1:13)
90%.

**Lenny Rachitsky** (1:14)
Wow.

**Jen Abel** (1:14)
Like, it's literally so fun. People read these salesbooks, go to these sales trainings, they try and take someone else's game and run with it, and it never works that way.

**Lenny Rachitsky** (1:23)
Most people think the sales process is five steps, and we're already in step 10, we're not even done.

**Jen Abel** (1:28)
The worst thing you can do in the sales process is...

**Lenny Rachitsky** (1:34)
Today, my guest is Jen Abel. This is her third time on the podcast. For those that don't know Jen, she's co-founder of Jellyfish, GM of Enterprise Sales at State Affairs, and most importantly is the person that I've learned the most from about the art and science of enterprise sales. In our first conversation, we went deep on founder led sales. In our second conversation, we focused on the $1 million to $10 million enterprise sales playbook. And in this conversation, we do something I've never seen anyone do on another podcast. We go step by step through the full enterprise sales cycle. Most people think this is a five step process. It turns out it's closer to 15 steps. Most people ignore a bunch of these steps that you'll hear about. We go through everything that you need to know at each step to significantly increase the odds that you close your deals. This episode is incredibly tactical and specific. You will learn a ton. I did for sure. Like I say in the episode, I always get so energized and just excited to sell something after talking to Jen, you will feel the same way after this conversation. I'm so thankful to Jen for sharing so much alpha with us. Before we get into it, don't forget to check out lennysproductpass.com for a free year of the hottest and most beautifully crafted AI products in the world, available exclusively to Lenny's newsletter subscribers. With that, I bring you Jen Abel.
Jen, thank you so much for being here. Welcome back to the podcast, a very rare third visit to the podcast. How does it feel?

**Jen Abel** (3:01)
Round three, super excited to be here, Lenny.

**Lenny Rachitsky** (3:04)
I'm even more excited. We're going to do something really unique with this conversation. I've never done anything like this before. We're going to basically go through the enterprise sales lifecycle, step-by-step. You'll talk about this, but many people think it's like five steps. You talk about how there's actually something like 15 steps. A lot of people ignore a lot of these steps.
The idea is I want to create a very concrete and tactical playbook for how to do enterprise sales.

**Jen Abel** (3:33)
Okay. We've had conversations. Making way by secrets.

**Lenny Rachitsky** (3:36)
That's the goal. Just suck them all out, make everybody amazing at sales, it'll be great.
And this touches on why I think the podcast is really helpful to people and just the valley vibe, even though you don't live in the valley. Just like there's so much win-win-win in helping people learn these things. It may feel like, why is she giving away all these things? But maybe actually, let me ask you that, just like why do you share these things?

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