What's the hardest thing about selling for startups?

This is a bigger question than maybe it looks from the outside. And my answer is only good if you want to learn more about the challenges that come with working in sales at a tech startup. 

But I've sold stuff, SaaS and native advertising successfully, so I have the tech startup sales world pretty well covered these days. 

The most challenging aspect of working in sales at a startup depends on your own personality. Different people resonate with different obstacles. 

I think about them like songs. Like all good tunes, some people will always prefer one over another. That's okay. There is a lot of great music in the world, and we all play favorites.

Pick your favorite tune:

Working Without A Net 
Waylon Jennings
Most salespeople do the work - they show up and execute the sales process the company has already developed for successfully generating revenue. In this specific way, most salespeople are a little like jazz musicians. They are social improvisers. But they need that structure to get started.

Most startup salespeople work without a net in the sense that they have to generate revenue without a proven process for doing so. Every startup starts out without answers to any of the tactical sales questions critical to the survival and success of a real business. Selling while creating the sales process is challenging in part because you have to use both sides of your brain at once. Your day-to-day selling tactics literally create your sales strategy. We learn how to sell. Or we die.

C.R.E.A.M (Cash Rules Everything Around Me)
The Wu-Tang Clan
The cash you bring in typically will be the fastest way you prove your worth. Most of the internet businesses that scale well are actually "monthly recurring revenue" (MRR) businesses. When you are selling for a startup, your first priority is to generate cash. In an MRR business, you will run into a cash crisis. Or three. For a couple reasons, it's just a structural inevitability. Impatient/inexperienced founders won't help. (When it comes to revenue, they're all impatient.) This is bad when you like to sleep at night.

Sales plans that don't depend solely on MRR to generate early cash flow will definitely help. Examples? Here are two: Banner advertising and Salesforce.com-style upfront payments on annual SaaS contracts. Both involve large cash payments with ongoing liabilities for services rendered. Both make it easier to justify salespeople to impatient investors and executives - and to pay them. Measure MRR, pay for ARR. You have to learn how to manage that risk, and you have to learn fast or die. Selling for startups is not for sissies. 

Walking On Sunshine
Katrina and the Waves
Selling is simple. You have to generate your own certainty, enthusiasm and confidence. And you have to transfer that enthusiasm from one person (you) to another (your customer). You have to understand your prospects. You need to know how to sell in your market. You need to master an effective sales process. You have to know your competition. Simple enough. 

Selling for startups is hard. When you sell a new product for a new company in a new market, you will doubt your product, be ignorant of your competition, and misunderstand your prospects. You may even have to create an entirely new market. Your sales chops matter a lot less than your learning skills in the startup environment. You will be expected to grow through pain and still transfer enthusiasm from one person to another. In other words, you'll walk on sunshine. Or die.

Walking on Broken Glass
Annie Lennox
Expectations are very difficult to manage when you're selling for a startup. You're constantly walking the razor's edge. On the one hand, we're free to become the next hero who kept the lights on while driving adoption of the next truly important innovation in human history. We too can be Omid Kordestani (Google's first seller). On the other hand, we're free to become one of those salespeople who did expense the damn golf outing. Who killed the company.

We have to learn how to manage expectations with our founders, our bosses, our peers, our customers, our investors, our sales teams and ourselves. And still, sell. Or die.   

Won't Let You Down
Startup sales guys face a constant succession of nasty challenges and high expectations. Change is the only constant. Pressure is the only certainty. Complexity becomes your best friend. We have no time. We have no power. We have no resources. We have no proven process. We will slay dragons. We will keep the lights on. We will sell. We will hit the number. And we won't let anyone down. 

So like I said - the hardest thing about selling for startups depends on you.