Enterprise sales are different from B2C sales: Sales cycles are longer, you have to talk to many different people, and it’s not done once the sale is complete.
At the end of each year, I review my files, notes, and contacts to keep things organized and clean up digital clutter.
The end of 2025 was no different. This year, I focused on organizing my personal notes, which I keep in Obsidian. I like Obsidian because it visualizes connections between different notes and topics.
My cleanup session revealed how many meetings and calls it takes to close and maintain an enterprise deal. Yes, that’s counterintuitive to all the hypergrowth talk that shaped the fat years that lie behind us.
Let’s look into some details of a few enterprise deals I worked on at Yonder, the B2B SaaS company I co-founded.
1. Sales cycles take longer than you think
No investor likes to hear that sales cycles can take longer than one year. But it’s a fact in many B2B markets. At Yonder, we are active in the aviation and critical infrastructure verticals, with sales cycles taking 1–3 years. That’s because customers usually make decisions only after an RFP process, and because winning an RFP means shaping it long before it is published.
Do you think I’m exaggerating? Do you think I’m trying to find excuses why hypergrowth doesn’t work in B2B? Let’s look at some real-life examples pulled from my personal notes in Obsidian:
Enterprise customer #1:
- Number of meetings and calls: 65
- 1st meeting: April 24, 2019
- Contract signature: August 19, 2020
Enterprise customer #2:
- Number of meetings and calls: 253
- 1st meeting: August 13, 2019
- Contract signature: May 21, 2021
Enterprise customer #3:
- Number of meetings and calls: 384
- 1st meeting: January 23, 2018
- Contract signature: March 31, 2023
To make sure the data is comparable, I have only included data from deals that I led from start to finish, from initial sales talks to RFPs and customer success.
2. Involve multiple people to get a deal done
Let’s dig a little deeper into why sales cycles are so long in the B2B and enterprise markets. Again, my notes database in Obsidian proves useful: I didn’t just link the company name to each meeting but also the names of the people attending each meeting. From this, I can see that many people were involved in the sales discussions.
In contrast to B2C, where each potential user is also a potential buyer, you have to speak to many different people when selling in the B2B domain. Sponsors, main users, procurement, legal, everybody wants a say in the discussion. That’s one of the core reasons why sales cycles are so long, and why you will need to schedule so many meetings and calls before closing an enterprise deal.
To make things worse, large organizations often do internal reorganizations, which means you will get new points of contact, and you will have to start all over again with your sales pitch.
3. After closing the deal, stay in touch regularly
Closing the deal is one thing, but it’s not the whole truth. Once you’re in business with a B2B or enterprise client, you will have to nurture the client constantly. If you don’t do this, you risk losing the client. Here are some reasons why you will have to do this:
- As many people were involved in the sales decisions, you want to make sure your key users like and understand your product.
- Onboarding sounds simple, but it isn’t. You want to keep an eye on the speedy rollout of your product for your customer to get the maximum value out of it.
- Yes, even after contract signature, enterprise customers undergo internal reorganizations. Whenever the point of contact changes at an enterprise customer, you will have to spend extra time to fully onboard the new person to your product. From my personal experience, taking key person changes too lightly is a main driver of customer churn — especially when they happen before onboarding is completed.
Last but not least, even when after landing an enterprise deal, you want to materialize an upsell, don’t you? I’m afraid you won’t be able to do this if you don’t talk to all sorts of people at your customer’s organization.
