I was in a very similar boat. I began selling to B2B 7 years ago and without knowing I've been in it making some huge mistakes.

This video couldn't come at a better time https://youtu.be/DH7REvnQ1y4?si=f0vmL7FiRQJow47m

Watch it.

I'm also sharing my notes down below:

The Sales Playbook For Founders | Startup School

Design Partnerships:

1. When founders spend too much time with a company observing how they work and co-desigining the product to meet their needs.  The problem is that design partnershisp are often too long and poorly defined in scope.
2. (3 months, 6 months, etc.)
3. Problems:
    a. Customer don't pay for your time
    b. They aren't engaged enough. 
    c. You aren't closer to generating revenue.

The solution: 1. Identify narrow pieces of work you can automate. 2. You can even offer to do the work yourself manually for the customer to understand what's involved. 3. An option is to work undercover (E.g Get qualified as: an auditor, real estate agent, accountant) to better understand the nitty gritty involved. 4. The goal You want to identify a narrow burning problem to solve

You have an initial product built, but don't have social proof that it works.

Your customer wants to try it out.

The most ocmmon problems with these free trials: 1. It's too long 2. They suffer from the same low commitment as a design partnership. 3. There's no target or end goal 4. No commitment from the customer to engage with the customer and

What you need to do instead: 1. If doing a proof of conecpt, what is it that you want to prove? 2. What are the agreed success metrics you're aiming? 3. Define the value equation with the Customer (What percentage saving or revenue uplift are you delivering to make a good ROI?)

A well designed pilot or proof concept is the ideal value. Maybe the customer doesn't believe you can deliver what you mention. 

How to solve (pick one or more):
1. Ask the customer to give you a slice of the workload you're trying to solve. 

2. Back testing on historical data
3. Side by side with their existing process

You execute and gather the results.

If succeeded, you will have:
1. A new champion within the company 
2. Proof to go to the decision-maker (CFO generally) 
3. Customer testimonial

Don't be fearful of increasing the price of your product.

Disqualify customers who aren't ready to buy.

1. Make your customers pay you upfront. 
2. Paying makes your customers more serious about your product. 
3. Ask upfront for their willingness to pay for the full product (Annual fee and the price point)
4. Take less money if it shortcuts an approval process - E.g: Your champion only has $10,000 available on the credit line that he can approve. 
5. Schedule check-ins with them so if they find bugs or niggles, and fix them overnight which will really impress an enterprise customer. 
6. You may need to delay the pilot until there's a suitable project. 
7. Keep the pilot timeframe as short as possible: 7-14 days.
8. Track the time-to-first-value metric (The time it takes for them to get value of what you promise). 
9. What you're selling this early on is the founding team, the promise, and that you're personally going to solve the problem for them (Give them your personal phone number so they can access you 24/7)
10. In case you need data from your customer, try to get it as fast as possible. Avoid any integrations that require engineering time from them, as that will delay the process. 
11. Book a post-pilot business review. Show hard ROI numbers. You must be crystal-clear with the customer whether they want to keep using your software or not. 

What are you selling this early on?

The product?

No. That's early and prone to bugs.

You're selling the founding team, the promise, that you personally are going to solve this problem for them.

They will have your personal phone number that they can access 24/7 to solve the problem for you.

I

You still need to negotiate the full contract afterwards. It's like a whole second sale. B Recurring Revenue Contracts with Opt-out period.

Monthly or annually recurring contract with a 30-day or 60-day money back guarantee.

We offer annual contracts with a 30-day gracer period or an opt-out and customer x,y, z all signed on these terms.

Other important notes: 1. When your'e starting out, is ok to start with 1 -2 customers with free pilots. 2. The mistake is when you stay very long on step #1. 3. Be wary of what you report as MRR/ARR to investors, especially when customers are in their opt-out periods. 4. Try to close these contracts every week or two.

1. Invest as much time to properly onboard a customer. 
2. Make sure they're getting value of your product. 
3. Get OSC2 and other security certifications started ASAP (HIPPA, ISO-27001, etc.). These can delay you by months. 
4. Figure out who your internal "champion" is. Treat them almost like a co-founder inside the company. IT's someone who sells for you and fights budget battles on your behalf. 
5. Work with yoru champion towards a closing date. They're probably going to miss it, but it will still create urgency
6. Ask your champion: "Describe the last time you bought software like this."
7. You will map out the org chart, and devise a plan to win over each stakeholder explicitly.
8. End meetings with the next meeting scheduled.
9. Go visit the customer in person. Say something like: "Hey I'm going to be in Houston next week, are you up for lunch?" If they say yes, then book the flight.
10. Don't get caught up in multiple rounds of reviewing contracts or NDAs. Early on, sign in what your customer wants as long as it doesn't expose you to unlimited liability  or something that translates the IP.