Enterprise Sales

"I think it does really play well in this enterprise sales context because also we have a group buyer there. So it's not just one person who's doing some research. This whole group has to have a uniting story."

"typically we have between five and seven people are involved in what we call making the decision for what gets bought. ... So by far the most important persona that matters is that one. We call this the champion in the account because this person, their job is to get consensus and champion the deal across everybody, including their boss, who's the actual economic buyer, the person that writes the check."

"In B2B, typical purchase process, we have five to seven people involved in making the deal happen... it is on you to arm that champion to handle all the objections potentially of all the other groups."

"Microsoft was like, "Wait a minute. We need to organize this. We need security. We need account management. We need procurement involved."... they wanted us to have this enterprise product, because they had these requirements and they wanted to have a better control over it, because it was just popping up within the organization without their control."

"Product-led sales converts the usage that you've generated via self-serve into a sales opportunity and it attaches a salesperson to close a much larger contract, which can be 15, 20, a hundred thousand dollars in order to bring an enterprise-level solution to a company that has already been using it in a self-serve manner."

"90% of product-led sales is converting the usage into an opportunity by finding a buyer outside, by finding the decision-maker outside. This is where marketing and sales are so crucial in the process. Connecting that decision-maker to the usage and then driving an opportunity through sales funnel all the way to closed one deal."

"One of the most important things is to create network effects within the company... any new sign-up that happens from the company that already has an account in my system should be presented with an option to join that account, not just create a brand new account."

"When you get to procurement, you're going to have to do all the work. Make their job easy. ... Give me the forms that you need to fill out. I'll fill them out for you, and you can do it yourself."

"Know who the signature is, because if they don't know what they're looking at, they're going to kick it out and you're going to lose your queue spot."

"I say the mid-market doesn't exist because what is a mid-market hire? It's either low end enterprise or upper end SMB, and if you bleed those two games you're going to lose. They're so distinctly different."

"Early adopters are those logos because they have to continue to stay at the number one spot. So they'll take tons of swings to continue to stay in the ... Staying in the number one spot is the hardest part. So those number one logos are like if you can give me just a slight bit of alpha, just a tiny bit, that's where I get promoted, that's where I get the pat on the back because we are the world's leader in our industry and we cannot be disrupted there."

"It's more of an art. It's all about deal crafting. It is a relationship you're building with someone. If they know they can call on you, people will turn over rocks for you."

"If they have a very immature way of understanding the problem or they've never purchased technology to solve it to some extent... selling them as service, even though the technology is powering it on the backend is the fastest way to get your foot in the door."

"The POC should be framed as the entire goal of the POC is to create a business case, period, full stop. It is not to demonstrate product functionality fit within your customer environment's ability to integrate. All of that stuff is a consequence of the business case."

"The right way to think about an ROI model is to actually co-create it with your customers from day one, which means agree and validate on the assumptions and the inputs... If you have done that process and the customer agrees on all the inputs, they're very unlikely to push back on the output of an ROI model."

"Outlook users are also used to certain safeguards, like if you've used Outlook in an enterprise, warnings when a recipient is external to your domain or what Outlook users might know as sensitivity labels... it truly is a multi-threaded sale with multiple stakeholders."

"Forward-deployed engineering, which on some level is kind of a rebrand of professional services but kind of not. And a big part of that is, hey, how do I actually get into your environment, ride alongside you better understand what you're trying to do and then help you actually bring the technology to life and learn a lot along the way."

"What we started to do at Stripe was that first session was a whiteboarding session, and we would actually get together and have you draw your architecture for payments and all the other things that were under the hood to enable you to take money and drive customer outcomes. And through that we would learn a ton about what was in your stack... But the customer also learned a lot themselves because in many cases they'd never drawn their architecture diagram."

"our analysis showed that anywhere between 40 and 60% of the average salesperson's qualified pipelines... will be ultimately marked as closed loss, no decision."

"The omission bias is, if you get down to it, is the fact that people don't want to be blamed for making decisions that lead to a loss... people are okay with missing out. They are not okay with messing up and being blamed"

"The first thing is we've got to judge their level of indecision... The second thing is we've got to offer a recommendation. The third thing is we've got to get them to start trusting us and we call it limit the exploration, and the T is we've got to de-risk the deal."

"We found a technique... called pings and echoes that high performers use... a salesperson will try to articulate but in a non, not to out the customer, but to get confirmation or refutation, if you will, that what they've articulated is actually a concern for their buyer."

"you've got to shift your posture from asking the customer what they want and just diagnosing their needs, to actually recommending to them what they should do."

"The first one is you've got to establish some trust... they are brutally transparent with customers about like, 'Hey, I know you were interested in this capability. I got to be honest, we get mixed reviews on that.'"

"What great salespeople do though is they know that while they'll stand by those claims... they try to kind of under-promise and over-deliver... 'What I'd rather we do is build your business case around a 5X improvement... Then, let's set up to over-deliver against that'"