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Jen Abel: recommendation

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

“They will not be vulnerable. They might assume it's being recorded because I think everyone operates under that assumption right now, but for the benefit of yourself, do not have a recorder present.”

— Jen Abel

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

Transcript context

…And they also aren't sitting there now listening to a pitch. Yeah, exactly. Now they're talking. Now they're conversing. Now it's like, "Okay, now it's fun. Now this person's not pitching me. I'm in a conversation and a dialogue." Okay, so now you're talking to them and they usually do a very brief open. They're like, "Hey," we didn't get a chance to look up the chief legal officers at SpaceX. Obviously, this is just a case, but whoever that person's name is, "I oversee the legal team and blah, blah, blah." "Okay, okay, great." They usually don't give you much. So they say, "Okay, interesting. How are you thinking about ... Do you guys have an AI mandate going on at the organization? How are you thinking about the existing way you guys are doing work? What are you looking for going into 2027? Does anything need to change?" Ask, "Does anything need to change?" Because again, what they're going to usually default to is what conversations have happened above them and have been transcended down. So the change is usually dictated from the top, which is great, "So what needs to change going into 2027 that you did in 2026 or maybe not at all?" And that's when they start to open up. And again, you don't want to be too pointed of anchoring them towards your product, because again, the more they speak, you can start to pull on the strings that matter. So they could say something along the lines of, I'm making this up at this point, but, "We are really looking to figure out how to bring more of this work in-house and rely far less on external law firms because now we have more tools and capabilities." "Okay, is there a measurement to that right now? What does that look like internally in terms of if you've done that successfully in 2027?" And then they'll say ... You're trying to understand how mature is this thought, right? Okay, so now they're going in and they say they can't really answer that fully. "Okay, why is that important now? Why not wait another year? You guys have so much going on. You just had this massive IPO. What's causing the team to want to reshape this or rework the way that they're managing internally?" And that's usually the moment of where they start to really guide you in terms of how they want to structure their team. So now you're getting all of this information about where they want to go, right? Now when you talk about what you do, now you're the vehicle to get them there, right? And so I try and spend maybe 10 minutes, the back 10 minutes explaining what we do and just keep asking them questions. Be like, "Oh, that's so interesting. What an exciting role to be in." Be like, okay, full disclosure ... And by the way, I take a step back to that. Do not bring a recorder to this call. Do not record the call. They will not be open. They will not be vulnerable. They might assume it's being recorded because I think everyone operates under that assumption right now, but for the benefit of yourself, do not have a recorder present. . They will not be vulnerable. They might assume it's being recorded because I think everyone operates under that assumption right now, but for the benefit of yourself, do not have a recorder present. Just be, "Off the record between the two of us talking right now of what you just shared, what really matters or what do you want to own or what's the chronological ..." Keep digging, digging deep, because the more you dig, the deeper you go, the more information they give, okay? Now you can't sit there and just pepper them with questions. This is that art piece of, "How open is this person?" Some people are poker faces, some people are not. You will be able to go much deeper with some and not deeper than others. You just have to improv, okay? But after you now have that intel and you can now understand, "Okay, here's the frame I'm going to take," now you can give them the pitch, okay? I will confirm every single conversation I have, the storyline that I tell looks slightly different. I do not have a scripted pitch or frame for any call because it feels artificial. They feel it. It feels like you're putting them into a square box. The best thing you can do is listen actively and then feel confident enough to craft the pitch around what they just shared for you.…

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