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Jen Abel: evaluation

23 Aug 2026 Lenny's Podcast How to close $100K+ enterprise deals, step by step | Jen Abel

“It's actually called the pincer model, which is start at the very, very top, find that floor and work in between that, okay? So these are the two layers you want to be targeting in landing that meeting, because if you go any further than that, you risk, they're not going to be able to communicate your storyline.”

— Jen Abel

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Speaker
Jen Abel
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Verified speaker
Claim type
evaluation
Recorded
23 Aug 2026
Publisher
Lenny's Podcast

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…And then a 100k, let's say deal, and to your point, it's the same process whether it's 100k, a million. And I will add a plug for a previous episode, you talk about why you want to be at least 100k something as a deal to be a real enterprise company that will survive because the ROI and just the whole economics of that stuff, but we won't get into that. This episode is brought to you by our seasons presenting sponsor WorkOS. What do OpenAI, Anthropic, Cursor, Replit, Sierra, Clay and hundreds of other winning companies all have in common? They are all powered by WorkOS. If you're building a product for the enterprise, you felt the pain of integrating single sign-on, SCIM, RBAC, audit logs and other features required by large companies. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Literally, every startup that I'm an investor in that starts to expand upmarket ends up working with WorkOS and that's because they are the best. Whether you are a seed-stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise-ready and unblocking growth. It's essentially Stripe for enterprise features. Visit workous.com to get started or just hit up their Slack where they have actual engineers waiting to answer your questions. WorkOS allows you to build faster with delightful APIs, comprehensive docs and a smooth developer experience. Go to workos.com to make your app enterprise ready today. Okay. Step one, where does it start? How do you start selling someone on your product? It's a great question. So I think let's start with how do I even get the first meeting, how do I even engage with these people. There's so much nuance as you target, as we're using the case study of SpaceX today. You have the top of the rung, which is the general counsel, the head of legal, the chief legal officer. They all have slightly different titles, but they all carry the same weight, which is like, "Who's the lead of the team?" And then underneath that, you have a bunch of people that carry a VP title, carry a director title, maybe just say lawyer on their LinkedIn. So you have to do the work to figure out, "What is my entry point?" and there's only two entry points, starting at the very, very tippy top, meaning going direct to the decisionmaker, the chief legal officer, or finding the individual that would be maybe one step removed, okay? Other people would argue with this. I personally would not be targeting anybody else. It is the executive themselves or an N minus one, okay? So let's talk about why. In order for an enterprise deal to move forward, you need to have this extremely compressed storyline that lands immediately to the objective that they want to solve for at the organization. It has to go beyond just an AI mandate. I think every company today has an AI mandate and I know everyone is an AI tool, but what exactly are you solving for them as a problem? That's one, that's level one, but most importantly, the alpha, "What does this executive uncover and unlock by bringing in a net-new tool?" Because bringing in a net-new tool is risky. No one wants it. So if we're targeting the chief legal officer and the N minus one, you get two to three sentences max, okay? That might be through an email LinkedIn, that might be through a phone call, that might be through an event or that might be through some marketing capability. Most C-level executives don't respond to marketing. They might see your brand, they're not going to respond to a marketing campaign, okay? They will respond one on one. And the best individual to one on one to a corporate executive is the founder. Even if you're a series B, series C, right? The founder should be ecstatic to want to get in front of the chief legal officer at SpaceX. I think any founder that is building something really meaningful knows the important role of that. Second is you can get your AE or enterprise sales lead to target the N minus one and you do what you call this ... I call it the pincher model because you're going after two different people and trying to get them together. It's actually called the pincer model, which is start at the very, very top, find that floor and work in between that, okay? So these are the two layers you want to be targeting in landing that meeting, because if you go any further than that, you risk, they're not going to be able to communicate your storyline. It's a game of telephone, right? layers you want to be targeting in landing that meeting, because if you go any further than that, you risk, they're not going to be able to communicate your storyline. It's a game of telephone, right? And now, you're learning from someone that is not near the budget or the executive discussions, which is super risky because now you're learning about user value, not executive value. And a $100,000 deal needs a executive sponsor to sign off on it, to allocate the budget and this is why you need to start at these two layers only.…

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