The Art of Skip-Level Selling

By David Frankel, Managing Partner

Imagine you are seated next to the CEO of your dream customer for dinner. Over the course of the evening, you’ll likely have 20 minutes to chat with this person about your startup. How do you make the most of this scenario (Or its socially-distanced simulation?)

A perk of raising from VCs is that investors often host dinners, office hours, and convene groups of high-level decision-makers. You’ll likely have opportunities to meet C-level execs in your industry earlier than the state of your business might dictate.

These are the closest thing you’ll find to cheat codes in the business world. An email from the CEO to a VP or director in her organization, endorsing your startup, however slightly, is a powerful door-opener.

Some thoughts on how to make the most of these opportunities:

🌟 Project confidence

The person you are pitching likely doesn’t know who you are, what you do, or why your product is great. They assume that because you’re in the room, you must have something going on. Lean into the perception. Part of the job is creating a sense of FOMO.

🧞 Explain new tech

If you’re deeply knowledgeable about crypto, TikTok, or some emerging form of tech, you can likely score points by educating this (likely more senior) person. The goal is to make the person think you’ve got magical insights about the future.

NB: Let your conversation partner lead you in this direction. You might be surprised at how savvy executives are about technology. There are few things worse than appearing to condescend to the person who holds some of your fate in their hands.

🌇 Pitch at a high-level

Entrepreneurs may be more used to pitching VCs who share a broad vocabulary and set of norms around startups. You can’t rely on this kind of shorthand in this setting. Start by setting the stage at the highest level.

📯 Drop names

One of your jobs in this “pitch” is to build credibility. Since you’re likely an unknown quantity, points of 3rd party validation are helpful. As much as possible, reference clients/partnerships that the person will recognize/trust.

🛡 ️Don’t get defensive

Your interlocutor is working at one or more levels of abstraction away from you and may ask some simple questions or challenge your assumptions. Try not to get into a debate, and instead attempt to find areas of mutual agreement.

I want to emphasize this: winning a debate likely means losing a deal. Not that you should be obsequious, but time is short, and the goal is to get the person nodding along with you, not believing you’re stubbornly naive.

📨 Know your ask

The goal of this pitch isn’t to close the sale. It’s to get this person to send an email to one of their reports endorsing your offering and instructing the recipient to take a closer look. That’s it. Work with that goal in mind.

🏟️ Prep a demo

Having a cool demo that you can walk your new friend through is a great tool to have at your disposal. However, be sure to be well-practiced — a buggy demo in this scenario is a killer.

These opportunities are rare but powerful, and they require a different kind of pitch. Each conversation will be different, but these basic principles should help you get a step closer.