This is an exciting week! After several weeks of heads-down development and product work, we’re about ready to release our billing functionality. Maybe that doesn’t sound sexy, but to us it’s where the rubber meets the road…will people pay for Dasheroo? Many have said they will be happy to, so let’s see.

But that’s not the startup lessons learned this week; it’s obvious when you are starting a business that you need to charge for your service. But there’s actually several lessons that this billing project has taught me, and I’m going to focus on a key one now, one that I learned at my last start-up and one that is being reinforced in my experience at Dasheroo.

And that lesson is that even with an SMB-focused offering, there’s a huge importance of establishing ‘larger company/enterprise’ sales efforts at the get-go. If that seems contradictory, hear me out. Here are my top 3 reasons we’re pursuing this strategy at Dasheroo:

1) Cash flow: In a business freemium model like we have, it takes a lot of $19 per month transactions to make a dent in the cash burn of our business dashboards company. Sure, it’s vital to build what we call the ‘auto-convert’ side of the business and establish our conversion metrics so we can begin modeling out what the business will look like 3-5+ years down the road. But I was reminded of my experience at my last start-up, VerticalResponse, of the value in generating cash NOW.

Similar to Dasheroo, VerticalResponse catered to the SMB market, providing a self-service email marketing platform. Most users paid less than $15 per month, and we knew we needed to offset our cash burn faster than those smaller sales could support. So we targeted companies with large email lists - e-commerce companies for example, that were happy to pay us thousands of dollars per month for the great email deliverability and VIP support we’d provide.

2) Diversification: Although the global small-midsize business market is well diversified with tens of millions of companies - we already have users in 100 countries from a gay pride foundation in Montenegro to a beauty school in Indianapolis to a dev shop in Guadalajara. But I’m talking more macro-level diversification from a sales perspective. Larger companies behave differently. They tend to buy on an annual vs. monthly basis. They tend to like ‘per user’ pricing and VIP support. All items that provide value to our larger customers that we are then able to charge a premium for.

3) Long term sustainable growth & value: This is an issue that really surfaces after you have achieved a level of success selling to SMBs. The spigot of early adopters tend to dry up a bit over time, and it becomes increasingly difficult to sustain the high sales growth rates of the early days. And ‘increasing at a decreasing rate’ isn’t something anyone wants to hear.

So have we landed a ‘whale’ yet? Nope, but we’re in advanced discussions with a few that we hope to come to agreements with soon. And it’s not just good for cash flow, it’s great for internal morale and to position Dasheroo for a better chance of providing long term value to our investors, and potential acquirers.

One note - take caution that one ‘whale’ doesn’t pull you out to sea with one-off feature demands that aren’t scalable to the majority of your user base! Happy fishing.