Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper (Part 5)

Sramana Mitra: When you and I started working together and we were looking for the positioning, that was very much our conclusion. It’s okay to cater to people who are coming as inbound leads and are a fit for the technology and product. But from an outbound marketing point of view, you have to pick a vertical and you have to remain focused and committed to get the full leverage of the methodology of getting a laser-sharp positioning in place. Talk about pricing. My recollection is that there were some discussions and debates around freemium and free trial on that front as well. Talk to us about what those decision points were.

Dan Stewart: We were, and remain, willing to experiment with pricing and with trials. On our very first site, there was nothing free. There was no trial. It was $19 a month. As we started to get a little bit of traction in the real estate space, we thought, “Wouldn’t it be smart to increase this?” We created an account that was 50 contacts free forever.

Today, six years later, we still have a bunch of clients who are maintaining their accounts at less than 50 contacts so that they can be free forever. One thing we tried, which was very effective, was eliminating the free trial and just offering the 100% money-back guarantee. Right from the start, we offered our service without contracts because we were just validating it. We didn’t know that we would be around a year later to renew a contract. It didn’t make a lot of sense to have one.

By eliminating that barrier, it has become something that we’ve become a leader for in the industry. In the real estate space, there are now several other companies that followed suit. We’re really proud of our results. We’re really proud that we can say, with certainty, that what we do really works and provides real value.

Sramana Mitra: Talk a bit about how it works contrasting do-it-yourself versus do-it-for-me.

Dan Stewart: From a very high level, it’s super easy to send emails today. There are dozens of companies that help people send emails. Most of our clients have those other solutions in place when they decide to use us. They don’t really hire us because they need to send emails. They hire us because they need to send emails that people want to read and would actually engage with. We offer our service in three flavors today. We have the brand new HG Touch where we provide content that’s written and refreshed on a regular basis.

That service is $59 per month. So far, most clients are just paying for it at an annual rate to get a slight discount. We’re charging $599 a year for that currently. A step up from there, we have HG Pro which is where we assign one of our copywriters to each client. We interview them and really get to understand their competitive advantages and their goals. Where is it that they fit in the market? Why is it that we would actually want to work with them if we were in the market for their services? We’d create custom content for that individual client.

On the technical side, we’re connecting to their lead sources so that as an opportunity is generated, whether it’s on their website or on realtor.com, our system is able to capture that lead and then trigger a campaign. We send those campaigns in three series of messages. The first is an acknowledgement message. It’s designed to get a quick reply from people who are near-term opportunities. We send a positioning phase which is designed to help the reader understand why they should actually want to work with this particular agent.

Then we send a long-term nurturing phase which helps the reader understand that this agent is really connected to the areas that they serve. It’s highly effective. We’ve won countless accolades and thousands of clients based on the strengths of those offerings.

This segment is part 5 in the series : Bootstrapping to Inflection: Dan Stewart, CEO of Happy Grasshopper
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