A Startup Sales Manifesto

The following is a letter we share with new members of the Lessonly Sales Team. Why share it? Well, I hope it sums a collection of experiences to answer a question that many grapple with: Why are we in sales?

Dear Teammate,

Sales is hard.

The job itself is genuinely tough (most startups claim it as the #1 challenge), but so is the perception.
Walk down the street and ask a stranger the first word that comes to mind when they think of “sales” and you can pretty much fill in the blank with_______________ (persuasion, fast talkers, deception, commission).

I was scared of these things when started I started “selling”, but what I’ve learned is this: sales doesn’t have to be that way. In fact, it really can’t be that way if you want to be successful.

You might have the same fears that I did, but I can tell you fervently that overcoming this fear is crucial for you entering this arena. It’s even important to confront for the masses who pretend “they’re not that kind of person” because as Dan Pink has reminded us:

“Like it or not, we’re all in sales now.”

So welcome. Joining our team, we think a few things are important to know.

The times you’ll feel most alive at Lessonly are when you put the team before any one individual. We’ll agree on a clear mountain to climb, and we’ll start manically focusing on how to reach the summit. Small teams are more fun than large ones, because every single step we take towards a new client directly impacts the trajectory of what we will become.

This is what gets me excited, and I’m excited for you to join us on this journey. Our goal here is to build a very human Lessonly Sales Engine.

I’ve asked myself why this is the case a number of times. After all, each of us could be doing a lot of things, being talented and ambitious people. Why are we on this path?

The people are wonderful

You may not know everyone yet, but I can tell you we have, at the core, a team that is unlike any other you will work with. The company we build and the success we have will help us give more people the opportunity to join an environment they will love; not everyone can say that because what we have here is special.

There is a thrill in competition

I’m not talking about competition with each other; I’m talking about competition with ourselves and with our competitors. The former is more about quieting our lizard brain, our doubts, our imposter syndrome. The latter means that it feels like the last leg of a 400m relay all the time. We are at the back of the pack, about to take the baton, with just one lap to catch the front-runners.

As a sales team, the baton is squarely in our hands, and it’s up to us to make it happen.

We have an unbelievable amount to learn

If we had a perfect blueprint, if we knew what the landscape would look like in six months, if all we had to do was show up, I’d hope you join me in walking out the door, because our work here would be done. We live in the opposite of this environment; if you grab the opportunity that’s here, you will sharpen a skill-set that will be invaluable and rewarding.

You’ve joined the underdog for a reason

Imagine for a second that we were the most well-funded in the space, had 3,000 customers, or were featured in Gartner’s magic quadrant — you wouldn’t be here. Joining the underdog is thrilling because you beat odds. You battle skepticism. You master the art of humble confidence because there will be limited belief outside of this pack.

So, I remind myself of these four things when I get rejected 10 times in a week, when we lose a deal to a competitor, and, on the flip side, when we schedule a meeting or close a new client. I hope you will do the same.

The best part of this journey is that you are the fuel that drives this ship forward. And when we’re collectively getting the job done, we will make enough money, we will become better humans, and we will have enough time and autonomy to pursue the joys get us up in the morning.

In the end, this will be damn hard. But I’m thankful we can make this Lessonly Sales Engine happen together.

— Conner

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