Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 6)

Sramana Mitra: You have $10 million in the bank. You started hiring sales people and started putting a process together.

Now, let me reask the question. What was the repeatable sales process?Was it that you started putting in a process to take all the leads? Are the free users categorized by companies, company size, and so forth and started having people call those companies?

Ryan Chan: I’ll tell you our story. I think every story is different. So we have always been 100% inbound. We’ve got a freemium product, basically meaning that people can sign up for the app, download it, and use it for free forever.

That enabled us to create this massive pool of people that just constantly use the free product. We hope that we’ll hit them at some point in their buying cycle when they’re in the right mindset to actually purchase. We’ve got this freemium product and we’ve got a massive database of people that have either once used it or are still using our product.

So the repeatable process was taking to core intent data. The first one is product usage. Then the second one is former demographics about this user. So the first piece was, we looked at how much are they using UpKeep. Are they super engaged with the product or are they not engaged at all?

That was one way we segmented our customers. The ones that are heavily using Upkeep, we knew that they had a higher chance to convert. Then the second former demographics was, we ran everything through Clearbit.

We still run everything through Clearbit. Clearbit would tell us what industry they’re from, how big that company is, who they are, and where they’re located. That will basically tie into, what we call, expected value of a lead.

We use these two different types of qualification criteria to judge who we’re going to go after, how we’re going to send emails to this person, and who we’re ultimately going to try to convert into a paying customer.

We obviously target the ones that have the highest chance of buying  and the highest chance to convert. That’s going to be based off of the title, company size, and then also how engaged they are with the product. 

Sramana Mitra: Were you asking the users to introduce you to the economic buyer or were you going to the economic buyer directly and then telling them that your organization is using this product?

Ryan Chan: We only target the economic buyer. It goes back to what I was talking about in the beginning where if we see a technician who signs up for the application, our goal isn’t really to try to sell him or his boss or make the introduction.

What we want is for him to just constantly use the application. But then we’ve set up triggers. The moment that person adds their boss or their manager to his or her UpKeep account, we get notified. That triggers this buying moment or potential buying moment for us.

So our process for technicians is to get them to engage with the product so much that they start inviting other people into his or her group. The moment that they do, that gives us the signal that this is the opportunity for us to go after that economic buyer. That’s the marketing side.

Then on the sales side, we can figure out the potential value. So we score every single lead that comes into the top of our funnel. Then we prioritize it. We go down the list. We send targeted emails. We’re hyper-focused on generating value to them.

I think there’re a lot of companies that just do these cold outbound calls that are super targeted towards the company. But we really try to flip that around and try to create a ton of value to the people that we are calling. For us, it’s not so much as, “Let me qualify you to see if you’re a good fit for UpKeep.” We want to go a step further to help them think about their entire operations and how we can help them as more of a consultant versus, “Let me sell you UpKeep.” I think that’s what has helped us reframe the sales cycle and the buying process. 

This segment is part 6 in the series : Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep
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