"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel
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You need to vision cast. You need to sell to a gap. Don't sell to a problem. When you're selling to a leader, you need to be selling an opportunity. The market doesn't want to be sold to, they want to buy.
Most founders would rather get 10, 10k deals than lose nine and get one 100k deal.
In the very early days, people will discount till the cows come home because they think that's the way to get a deal done. The best clients are not going to do that to you. If they're sitting there nickel and diming you, they're not fully bought in on what you're selling them.
It might be giving you a false sense.
Of success and product market fit. As soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. It's all about differentiation. Here's what you will be able to do tomorrow because of how we're gonna serve you today. Something else that you talk about is that enterprise sales is very creative. It's more of an art. It's all about deal crafting. It is a relationship you're building with someone. If they know they can call on you, people will turn over rocks for you. I have a client at a Fortune 10 company where I was like, it's so important we get the deal done this year. Is that possible? And she's like, it's a tall order, but like if it's gonna help you, let's do it.
These are how enterprise deals gets done. It's relationships.
What's kinda like the state of the art on go-to-market outbound tooling?
I don't use a tool. The thing about AI tools is they're all pulling from the same databases. I wanna email someone not in the database that's getting hit by a million folks. I wanna take a back door in, not the front door where everyone else is. Trick-or-treaty.
Today, my guest is Jen Abel, co-founder of Jellyfish, where she and her team help early stage founders learn how to sell, and now GM of Enterprise at State Affairs. If you want to become better at selling your product, this episode is going to blow your mind and make you so much better in every way. This is the second time Jen's been on the podcast. Our first conversation was focused around getting from 0 to 1 million ARR, essentially founder-led sales. This conversation is part two, going from around 1 million in AR to around 10 million. This is the most tactical and in the weeds discussion you will find anywhere for free on how to actually become more effective at selling to enterprises. I am so excited for you to listen to this conversation.
If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual Subscriber of my newsletter, you get 17 incredible products for free for an entire year, including Devin, Lovable, Rep Lit, Bolt, NADON, Linear, Superhuman, D Script, Whisperflow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, Chappie RD, and Mobbin. Head on over to Lenny's Newsletter.com and click Product Pass. With that, I bring you Jen Abel after a short word from our sponsors. Here's a puzzle for you. What do OpenAI, Cursor, Perplexity, Vercell, Platt, and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS.
If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, skim, RBAC, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs. With a modern developer platform built specifically for B2B SaaS. Whether you're 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 unlocking growth. They're essentially Stripe for Enterprise features. Visit WorkOS.com to get started, or just hit up their Slack support where they have real engineers in there who answer your questions super fast. WorkOS allows you you to build like the best, with delightful APIs, comprehensive docs, and a smooth developer experience.
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