15 Things I Wish I Knew About Selling Before Starting a Company
By Noah Jessop
It was a big pitch meeting. We’d been trying to schedule coming to the company’s offices for more than 4 months — after two cancellations, we were finally here.
We thought they’d be a great customer, and could genuinely get a lot of value out of our product. I pitched my heart out, showing all the features and careful thought we’d put into the product to make it really easy to use and incredibly powerful.
At a lull in the conversation, my new head of sales took over. He looked our customer in the eye, and slowly, almost quietly, said:
“Before we go much further here…are y’all ready to make a buying decision in this quarter or the next one?”
Our would-be customer was nonplussed and quite open: “oh no…unfortunately I don’t have the bandwidth or software budget to roll out an implementation for at least 3–4 quarters.”
I sunk down in my chair. In 3–4 quarters without some big sales, we would likely be out of business.
And this is when I realized that I’d been asking the wrong questions all along.
A sheltered teenage kid, more likely than not, likely knows less about the “real world” than a journeyman nightclub bouncer. Same is often true for new founders and technologists — who haven’t had the reason to have as much exposure to the messy realities of our business world.
Here are my rules — that I wished I had when starting out. They aren’t meant to be conclusive or complete. They are just supposed to help get things done.
Getting Out There: Introductions & Meetings
1) Learn the art of a good intro
Always get “double opt-in” intros — where both parties have agreed to be introduced. If you meet Alice and she offers to connect you to Bob, after the meeting, send Alice an email subject line “Intro to Bob?” with all the context Bob would need to decide if he wants to meet you. That way Alice can quickly forward your note with her context to Bob. If Alice offered to introduce you to multiple people, send her multiple emails to forward.
Once you’ve been connected to Bob, if you asked for the intro you should be the first to reply. Don’t wait for Bob. Move Alice to BCC, she’s already been kind enough to introduce you.
2) Specificity >> Generality
When you reply to Bob, you may think it’s kind to accommodate his schedule. (I can meet anytime in the next two weeks — let me know a day/time that works!) This is actually unkind. It’s harder for Bob to decide what day, what time of day, etc he’s going to sacrifice his open schedule, his before work pilates class, etc.
If you say “can you meet next Tues or Wed at 1, 2p PT?” you are constraining the problem and making it easier. If he has only a few times available, he’ll suggest those times; and if he has an open schedule, it’s easier to just say “yes” to the times you propose. Researchers have found people are far more likely to be available at proposed times than general availability.
3) Speed & consistency are proxies for trust
When first getting to know someone, we all use whatever signals we have available to try to paint a picture of this person. If you quickly and consistently reply to emails, many people will simply use this as a measure of trust. This is not to say to be overeager at all things — merely that slow or spotty responses before meeting someone don’t lead to a feeling of trust.
4) Make the message simple
The minute you try to explain anything over email, stop. Don’t be afraid to be high level. The goal isn’t to explain, convince, sell, and close over the first email. The goal is to get to the right person. Short of the right person, someone who is willing to help you get where you are trying to go. No more.
5) Simple words will do
Really. Same with short sentences. No peer-review here.
Bullet points > Paragraphs.
Try to keep emails <250 words.
Frame questions so the possible answers are “yes,” “no,” or a specific piece of data.
Run The Meeting
5) Set context
Else someone else will. Why are you here? What are you hoping to learn? What’s the best next step you can get from this meeting?
Remember, most enterprise sales (and other processes) aren’t transactional — any process you run will take 5–10 meetings. So how can you advance that process today? What are the hurdles? You have to drive.
Bring whatever materials will help you get to the next step (product samples, pitch deck, etc). Even if you don’t take aids out of your bag, you’ll be ready.
6) Steak without sizzle is stone cold
You have great intellectual property — or have built something very impressive. Just because you have lots of substance (steak) doesn’t mean it looks appetizing. It’s the vision and possibility (sizzle) that excites customers and investors alike. — how can your product change the way they do business? Or fix their most burning problem?
If you are having trouble with sizzle, imaging how someone would try to sell vaporware to your customer base. Or how you’d have to present if you had none of the credentials you likely already have.
7) When you get the next step, leave immediately
Potential customer agrees to bring in a key stakeholder for a future meeting? Leave.
Potential investor agrees to look at financial model and begin diligence? Bring the meeting to an end.Leave.
Once you have gotten what you’ve come for, you can only reverse the progress you’ve made. Gracefully wrap up the meeting, ask if there are any questions, figure out next steps, thank the person for their time, and be on your way.
(If you have trouble signaling this, try packing up your possessions while bringing the conversation to an end.)
8) Follow up on what you said you would
You’d be amazed how few people follow up. Said you’d send along an article? Send it. Deferred a question? Send the answer.
No need for lengthy thank you’s — a simple “great to see you today, thanks for making the time. Please let me know when you’ve determined best next steps there” or similar will do. Attach a copy of your collateral so the person can simply forward your email and make progress to whatever you agreed the next steps might be.
Email is likely the other person’s workstream. Use it to your advantage, while the meeting is fresh.
9) Get the follow up set ASAP
Potential customer agrees to meet in a month to take next step? Pull out your calendar at the end of the call and try to book a date. You’ll save chasing the person by email for weeks (and know if they are really serious). If they seem resistant, ask if it’s ok to put a placeholder — you can say in the meeting invite “To Be Confirmed” so they have the leeway to move it a week or two down the road. But you at least have something on the books to work from.
(This works for other things, too — and has aptly been dubbed the “Collison Installation” after the urgency of the Collison brothers, the founders of Stripe.)
10) Be persistent
No one will ever judge you for being persistent — you are starting a new company, that’s precisely what you should do. It’s ok to follow up when people aren’t replying to your emails. Everyone is busy and trying to their best.
(When I was first starting out, sometimes I’d make up elaborate stories in my head about what someone might be thinking about about me or my company — more often than not, it’s that they were thinking neither me or the company at all!)
Close the Deal
11) Ask for the sale
It may sound overly simple. It’s what the best sellers do. It’s the fastest way to learn if someone is serious. And it’s a great way to get to a conversation about what hurdles remain.
12) Pick up the phone
After spending time with someone in a sales or fundraising process, don’t be afraid to pick up the phone and call. This doesn’t mean to be salesy.
But we’re all humans, and respond to the human element of business. Also it can be way more time effective to get to no than weeks of waiting for emails. And faster to catch your prospect when they are free vs. scheduling weeks into the future.
Not a tactic to abuse, but one to not be afraid of trying. There’s no time like the present.
13) Be (slightly) unreasonable
Having trouble getting a meeting with a potential customer?
Be “in town” and then book the flight once the meeting is confirmed.
Not going to happen this quarter due to not having enough engineering resources?
What if our engineers came onsite and we did the integration?
Booked back to back next week?
What if I come sit in the lobby until you have a gap in your day? Note: This tactic is great if the customer has a waiting room the size of a small suburban home and is used to receiving lots of visitors. Don’t do this to a startup or VC firm that’s got 1,000 square feet total or you’ll come off as a creep.
Having trouble finding a phone number to ring a decision maker?
A friend of mine was fond of FedExing disposable cell phones to people who were hard to get a hold of. Wait until the package is signed, and start dialing away…
(We’ll save more of these tactics for another day, another post.)
Showing you want the business and are willing to outwork the incumbents goes a long, long way.
14) Reward the business
Even a simple hand-written note means a lot. Your customers have likely taken risk by choosing an upstart. Show them that you care and that you are there to build the relationship for the long-haul.
15) Have fun
Getting out there can make us feel vulnerable. It’s easier to avoid rejection or lack of reply from home, or hide away by building product and other internal things. But any process in the world is a hand-to-hand combat sport. Learn to love the process, enjoy the people you get to meet along the way, and refine your skills.
Some of my most vivid memories of operating were on the road, getting coffee in some strange cafe (#1 value: close to customers office), getting ready for a meeting where I had no idea what might happen.
Make memories, make friends, and enjoy the journey.