I've been in tech sales for nearly a decade. I navigated everything from the traditional nine-month sales cycle, all the way to high-velocity one-call closes.

There are two deals that really stand out in my career. While at the time I was skeptical of the value of these deals, I was proved wrong. Both deals originally came from freemium users and taught me the value of consultative selling—helping existing users get more value from our product.

"Try before you buy" got us executive buy-in at a healthcare company

The first deal was with a large healthcare company. The director of analytics saw our Instagram ad, and he downloaded the tool. He played around and created two or three widgets. Then he shared that with his COO.

That's already pretty exciting, right? I mean, these were executives at a large organization, and they had begun taking core actions in the product.

But the director wasn't done researching us! He then went onto our website and read about our security. Even before our first call, I already knew they were existing users who wanted to talk about security.

I decided to reach out to him saying, 'Hey, it looks like you have a pretty decent understanding of the product base.' I sent him some graphs of his usage. He threw some time on my calendar without responding (shocking how many people do this) and then added a bunch of executives to the invite. Not a bad first disco call, eh?

The day before the call, I sent him a confirmation email and asked if there was anything in particular he'd like added to the agenda. I had a feeling they wanted to know about security based on their website signals but wanted to let him guide the conversation.

Then he was like, 'Yeah, we used your product and loved it. We have some questions about SOC2 Type II and HIPAA compliance.'

And with that, I was no longer walking into a security call blind. We got our security engineer to join and were prepared.

The cool thing was as activated users, they were already sold on the product. All I had to do was unblock their concerns, which in this case happened to be the friction that lays outside of the product.

Word-of-mouth helped us win over an insurance company

The next story also involved a highly regulated industry—insurance.

This woman discovered us through word-of-mouth. One of her interns had shown her the product. At the time, they were already undergoing a big internal initiative to solve exactly what we offered. So she told me, 'If you can impress our security person, I will buy. I don't care what the cost is.'

They were already convinced of the product's value. In fact, they were product champions! I just had to navigate them through the security and procurement process.

These are the conversations that we salespeople love, because that's buying intent. Remember, people don't care about security unless they're ready to buy. Compared to traditional sales processes, it was astounding how quickly they were already at the bottom funnel.

What if they never happened?

What if these two customers weren't able to sign up for free? Or what if I hadn't been aware of their activity? I may have never closed these deals.

Freemium users are the newest channel (also known as a 'route to market') for sales teams. Many are already product advocates. We no longer have to convince them about the product's value. Instead, it's just negotiation of the package, security, etc. This changes the sales role from hard selling to helping—specifically, helping users sell internally and navigate the procurement process.

Because product-led sales is in its early days, I don't take it for granted. These are great leads and opportunities that we could have missed. Imagine the huge opportunity cost involved!

In retrospect, it would've really helped to have product qualified lead scoring and rep alerts instead of manually looking at website visitors, comparing those domains to our signups, then looking at another dashboard to see who was activating on our platform. That's really the best way to not lose out on existing revenue in your user base.

Which makes me wonder—how much revenue are you missing without a product-led sales motion?