For episode 3 of our newly launched podcast, Ground Up, I talked with our CEO, Pete Caputa, about what it takes to generate your first 100 customers.

Pete has been through this a few times. First, for his event marketing startup wherein he was selling event marketing software. Then, as an early employee at HubSpot, Pete remembers the 100th customer party (and the Natural Light and pizza that followed) en route to much bigger things.

Now on his third go ’round of building a customer base, Pete has helped Databox zero in on a beachhead market to gain traction.

I spent some time picking his brain to talk through recurring themes, across three different companies, that surface on the road to 100 customers. Below are just some of my favorite soundbites from the episode.

Hear the full episode on:
1. iTunes
2. Soundcloud

1:1 before 1: Many

In the early 2000s, Pete founded an event planning software company that built a web application aimed at helping people market their events and manage registration.

“I’d go and sell event planners on the idea of using the software, I’d go to venues and event planners and pitch them,” Pete said.

I remember I walked into an ad agency in Worcester and asked for a few minutes. I gave him the 10-minute spiel, and he said ‘come back to me once you’ve proven it out.’ That’s the response you get from people during that stage. They’re thinking, ‘I have an established business, I’m not going to risk using you and be your guinea pig.’”

Pete ended up promoting 200 events (over several years) using the software and eventually hit a critical mass of customers, but it was only after a ton of pitches that went nowhere.

“Eventually I had to learn how to sell because all I was going in with was an idea. I was an entrepreneur. I didn’t have the network. I didn’t really have any proof points. I just went looking for people who’d give me a shot. Nightclubs, small bands, just anything we could do to get traction, and one success led to the next.”

Think small (initially)

Digital marketing has changed the competitive landscape for everyone.

“So many companies are doing digital marketing, and there’s no barrier to it, so the competition is ridiculous. Because of that, older marketing principles have become more important.

I remember pitching my first startup at WPI Venture Forum (at Pete’s alma mater, Worcester Polytechnic Institute) and I remember the marketing person saying, ‘you need to pick a market.’ I’m like I don’t need to pick a market, that’s dumb. Everything works on the web.”

Now you can’t even think about doing that. You have to think about the MVP that will resonate with a relatively smaller niche group of people or companies. That’s how you’re going to get your first 100 customers now. You can’t try to emulate what bigger companies do and go after a big market all at once. You won’t have the resources to compete.”

Know the end user

When Pete first came to Databox, the funnel was so varied that it made it tough to sell, onboard, and service customers in a way that was repeatable. To help.

“One day I talked to the operations person at a fortune 500 company wanting to produce reports for their boss.

The next day I’d talk to a solopreneur or marketing consultant.

Then I’d talk to someone at a tech startup about to launch a mobile app.

The funnel was so varied that it would’ve been really hard to sell and service to all of them. The prospecting approach into all of these areas is going to be different. When you’re small, that’s hard to adapt to.

Because of my background at Hubspot and with marketing agencies,  I had started introducing agencies to Databox before I joined and I saw a kernel of what was there, so that’s what we focused our initial marketing and sales resources on. Helping agencies get a better handle on monitoring all of their clients’ data all in one place so they can stop cutting and pasting into documents.

Pete has also run a mastermind group of professionals from around 20 marketing agencies for over 5 years. He leverages this group to solicit feedback and bounce ideas off of.

“As we built the HubSpot partner team out, I got more and more removed from the front line, so I wanted a direct line to the marketing agencies to understand how HubSpot was helping them and what they were struggling with. I’ve kept up those weekly calls with 20 or so agencies for all these years. When I joined Databox, I introduced the product to them and asked them how it could help and what it could best be used for.”

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