There are only two jobs at an early stage startup: Making the product, and selling the product. That’s it.

Here’s how to sell the product.

Contrary to popular belief and movies that lionize sales: You can’t sell until somebody is ready to buy. And you don’t know when they’re ready to buy.

Every other human brain is (to you) a random number generator. Once a year it might fire “1” (yes). Your job is to make sure you show up around this time, or are remembered such that they call YOU when it fires a “1”. Most of the time it’s a “0.” Sometimes people only change their mind when enough time has passed, irrespective of data (https://www.arampell.org/2023/09/01/when-to-escalate-vs-wait/).

Bother the person every day and they’ll get a restraining order. Hire an Ivy League kid afraid of rejection who nudges them once every 5 years, and they’ll forget who you are when their brain (or circumstances) finally says “yes.”

We consequently had a rule: everyone should hear from us once a month. You need to mix up the way people hear from you. We had light, medium, and heavy. Light might be a personalized email or forwarded news article. Medium would be an in person visit (often “I happen to be in the area…”). Heavy would be an event or gift.

This rule applied to current customers (account management), prospects (sales), and strategic partners (see my thread on selling your company: https://www.arampell.org/2023/01/04/how-to-sell-your-company/). Everyone must hear from you every month or on some regular cadence.

One year at TrialPay we were sending out very nice, customized gift boxes. It seems kind of cruel to throw away a plant (versus, say, a cheap mug or t-shirt), and nobody can kill a cactus since they can survive in a desert. So we sent everyone a cactus in a blue, dinosaur TrialPay pot. When visiting customers for years to come, I always saw that pot. When their brain said “maybe I should use that alternative payments thing” there was a cactus staring at them with our logo, and likely an email within a few weeks.

If you’re selling to somebody important, you need to remember they are overloaded and you are their last priority, but there’s a secret way in: the Executive Assistant. My dad taught me this trick. Send a nice gift to every EA every year and you’ll be stunned at the results.

The former President of PayPal once took a 6 week sabbatical and when he came back he was stunned that I was the first meeting on his calendar. We had breakfast and his first words: “How the f*** did you become the first meeting on my first day back?” I smiled.

The way to model most big company behavior: anyone can say NO, but nobody can say YES. How do you get to yes?

You need to sell horizontally; everything above applies to probably 5-10 people in the organization you are selling into. You need to prevent the NO from crashing the party.

Next: building awareness. As I’ve mentioned, normally you can’t sell to the CEO since your product is likely not one of their top priorities:

https://www.arampell.org/2018/01/13/dont-just-sell-to-the-ceo/

https://www.arampell.org/2022/12/08/the-goldilocks-zone-of-cost-irrelevance/

We had tons of competition, companies that did the exact same thing as we did, making all sorts of grandiose claims.

So my job, as CEO, was to position us and myself as an expert in the space. How? By ensuring that we became the source of truth for the press, and an “expert” to the CEO’s actual bosses: Wall Street and analysts.

Since I was trying to both make the term “transactional advertising” a thing and get through to PayPal, I reached out to every single analyst who covered eBay. Cold (and once a month until they responded!), but with lots of thoughts around where payments were going.

It was pretty cool when one of them eventually asked the CEO of eBay what his plans with transactional advertising were. “You mean…like…Alex Rampell’s company?” Boom. Inception.

The same applied for the press. I once was told that the Press never wants to be too fawning over any particular subject, such that they’d have to write something bad about Mother Teresa just to be balanced. We got great one-off standalone articles in the NYT and WSJ about us, but what now?

The answer: come up with a metric that YOU OWN. Who could uniquely talk about conversion rate for Facebook games? TrialPay! Or abandoned shopping cart rates. Etc. Thus rather than having a standalone piece, my goal was to have an “According to TrialPay…” in every single article.

And then these press pieces were fed into the “once a month” engine. You need to assume that NOBODY reads these (statistically true!), so your job is to use them as external credibility and sheepishly send them out, include them in marketing collateral, etc.

Because when you have a 5 horse race and you need to win, you need to SHOW that you’re the market leader with external validation, and you can’t get caught up in the lies of marketing collateral where everyone CLAIMS to have features X, Y, and Z or even customers A, B and C.

Lastly, for most products, there’s plenty of selling that needs to happen AFTER you’ve sold. Your existing customers should still hear from you (at least) once a month, and you should set clearly defined goals for your account management team. More on that later.