What's the hardest thing about selling for startups?

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. 

The surprising thing about empathy

The surprising thing about empathy

Empathy is not a new skill, and its value still cannot be overstated.

Dale Carnegie published How to Win Friends and Influence People in 1936, so people have tried to "Become Genuinely Interested in Other People" (Chapter 2) for at least 81 years. But in The 7 Habits of Highly Successful People, Stephen Covey observed: “most people don't listen with the intent to understand – they listen with the intent to respond." And my 10 years of experience tells me that sounds about right. In tech sales, our last few years have been devoted to managing Challengers, playbooks, metrics - and measuring empathy is hard. But seeking to understand before being understood - applying empathy - recently became trendy again.

Atticus Finch taught us to understand other people. "You never really understand a person until you consider things from [her] point of view... until you climb into [her] skin and walk around in it." When we practice empathy, we seek to understand the emotions of others. Done well, we mirror someone else's feelings by connecting to their limbic system. We recognize what drives their behavior. You can't do that with language. It's not an analytical skill. Biologically speaking, it's arational. It's an observational practice. In simple terms, empathy is noticing, understanding and responding to the details that matter to other people.

Here's a story about applying empathy - by seeking to understand, first - in order to influence another. I hope you find it useful.

Her name is Bit Posey Smith - we call her Bit (you know, like the smallest thing). Bit is about 7 months old. She weighs about 5 pounds. She's a Jack Russell Terrier and Yorkshire terrier mix with some kind of tiny dog thrown in. Bit loves our 8-year-old boxer, Fenway. My wife and I rescued her from PAWS Chicago last year. She just got back from 2 weeks at a sleepaway training camp for puppies. Now Bit sits to say please. She walks away from something when she hears "leave it." And she barks when she dislikes something. Camp taught Bit at least one bad habit plus some good ones.

Here's our little Bit (she's the scruffy one on the left

Bits life has been snowfall in winter. From her point of view, outside is the pits: The cold air makes her shiver. The salt on the ground burns her feet. Bigger, more dominant dogs make her cringe. One of them kicked her yesterday. For Bit, outside means she's on her belly, cold, and her feet burn - in other words, she's miserable. From her point of view, outside is #1 uncomfortable and #2 intimidating. How would that make you feel?

So potty training Bit has been... a challenge. All the trainers say crate training and having your pup go outside is the only way to effectively potty train. But Bit won't go outside. Like, at all. Not for my wife and I anyway. Not in winter. In the wild, Bit's mother would immediately remove any waste or waste smell from the den. That's how puppies learn dens are not bathrooms. The crate teaches puppies not to go indoors by making them live in it if they go to the bathroom in the crate. No scent control - no puppy mom - needed. But that first night Bit informs us she does not like being stuck her crate. And my wife cannot sleep through it.

Jerry Weissman among others taught us the truth about communication - that communication with others takes place when they understand what we want them to understand and not before. When there's no Aha! moment, we are not communicating. Doesn't matter how many words, pictures, videos or calculators we use. People understand things in terms of their own experience, which means we must get inside their experience. When we go outside someone's experience not only do we not communicate - we cause confusion.

Let me show you what I mean. Bit started to bark. Very rarely but she started barking indoors. We told her "no" when she did that. Then she barked more often. Turns out a short word like "no" just sounds like noise to a dog. Brevity in puppy-speak is not a virtue. Unless there's conscious effort behind your sound (unless the noise in the "no" continues for some time) then there's no meaning in it. She makes a little noise, we make a little noise. A dog interprets that exchange as exciting. We took our little pup outside her experience, and she got confused.

The misunderstandings continued. We asked Bit to sleep in a crate. She spent the night crated for 32 days straight, and all the noise told us clearly she was not asleep while she did it. We asked Bit to "go outside" in the winter. She went outside, and then spent all her time huddled next to the space heater or peering intently at the door she came in - waiting to go back inside. And she punished us for it by leaving little "presents" for us all over the house. If we wanted to communicate effectively, we had to give her an experience.

So we're back to our potty training problem. We can't use the crate to communicate with our puppy. And we can't take our puppy outside because she isn't built to live in the environment outside. She understands scent control. She understands who is dominant and who is not. She's a dog. So we act like a dog's mom instead of a dog trainer.

How do we channel our inner puppy mom? Thanks to spending time at home, our house is already marked with our scent. We make it very clear where waste scent is allowed using puppy pads (think more like a litter box than a diaper). We remove waste scent immediately from anywhere it is forbidden. And we persist. In 1 week, our little Bit had 2 accidents. In 1 month, she's become more fastidious about our house rules than our other dog. Now she goes indoors in her assigned spot.

This is what it means to first understand, and then seek to be understood. We observed to understand what mattered to her. We communicated our expectations from inside her experience. She heard us. And we all benefit. I mean, how cute is this little scene from our living room:

Bit is potty trained now. #InterspeciesCommunication #proud

The Fundamental Playbook

The Fundamental Playbook

We seek to become better sales professionals. We love our customers. We want to deliver required outcomes and appropriate experiences to make them successful. And the only constant is change. So everyday we focus on two words to achieve this goal: No surprises. 
“I wasn't real quick, and I wasn't real strong... so I beat them with my mind and my fundamentals.” ― Larry Bird
Never sell alone
Let me start by issuing you a challenge: become better than you are now. Set a goal that seems unattainable and when you reach it, set another one higher. The secret to achieving this goal is always the team. Winning as a team is impressive. Winning as a team is memorable.
Sales is the transfer of enthusiasm from one person to another. Be assumptive. Smile. Breathe. Know your power. Let them hear it. Act as if we’re a big deal. Share excitement for a larger vision. 
Get close to believers

Find our believers: the innovators, the early adopters, the committed ones. The ones who depend on us. Learn their excitement. Learn their stories. Make friends. Be fierce champions of our believers.
Get prepared
Winning starts with unspectacular preparation for our next sales call. Always prepare an agenda. Always prepare your next steps. Always know your buyers. Know where they are in their buying process. Always know the next steps you want them to take.
"The key is not the will to win. Everybody has that. It's the will to prepare to win that is important."
― Bobby Knight, Indiana Hoosiers Basketball Coach 
Get curious
Hope is not a strategy. Our strategy is curiosity. So learn more things. Reach more people. Ask more questions. Be genuine. Be mature. Be candid. Be direct. Always get curious.
Get humble
We are understanding. We are flexible. We adapt to the situation. We are open to the ideas of others. We embrace the suck. There is always something new to learn. We learn by getting humble and keeping it. Nobody stands taller than those willing to stand corrected. 
Legs feed the wolf
A million dollar dream deserves a million dollar work ethic. Our job is to be on the phone with our customers. When we’re on the phone, we give ourselves options. We build relationships. We discover things. And video calls are better! More than 3 hours of call time, every day.  
"The legs feed the wolf, gentlemen." ― Herb Brooks, U.S. Olympic Hockey Coach  
Fill the gaps
Every customer is an opportunity. Either we have a plan to win each opportunity, or we're losing deals. The gaps in our opportunity plans teach us the vital questions. Ordinary sellers can't find them. Good ones avoid them. We run towards the gaps, and we fill them. This is our superpower.
No small deals, only small minds
Big deals require trust. Doing deals creates trust. Every deal builds credibility. So earn the right. Do more deals, and we’ll keep more customers. Do more deals, and we'll get to know our customers. Do more deals and we'll get to do bigger ones. No such thing as a small deal. 
"It's the little details that are vital. Little things make big things happen." - John Wooden, Basketball Coach 
Players make plays
We do things others won't. We do things others can’t. We set unreasonable goals. We do not quit. We outdo ourselves. We know we will win. We do the deals that change the game.  
Climb the Mountain