Startup Lessons Learned: Sales Strategy – Shut Up & Save a Sale

Sales Strategy: Shut up and sellHave you ever been in a situation where you or a colleague keep talking after your prospect or client has already decided to purchase? I know I have been. If you don’t read on you could snatch a “no thanks we’re not interested” out of a sure sale.


What reminded me of this was a recent trip I was on. I had to go through Paris several times over a 2 week period. So on the first trip out of CDG, I met a taxi driver who seemed great – clean, nice car, good driving skills and pleasant. I told him I had several more trips in and out of the airport as well as trips within the city. He eagerly gave me his card and told me to please use him for all the rides. I told him I’d take him up on it. He just got a nice sale!

A few days later, there he was right on schedule to take me to Orly airport. It worked out great, I got to know him a little better and found he was a well educated guy with a nice family. At that point he was batting 2 for 2 and looking to get lots more fares. Then…it happened. On the pick-up when I returned to Paris, he messed up my arrival time and ended up sitting at the airport for 2 hours. His first words for me were “you told me the wrong time!”  Who doesn’t use their phone to confirm flight times these days anyway? I told him to check the email and txt threads, where I had clearly communicated the exact arrival time & gate info. He argued a bit then wisely let it go. Thank God.

I was ready for a calm ride after that and would have let it all slide and continued to use him. I understand that time lost is money lost. But nope, he had to do it, yep,  bring up politics, and went so far as to say “how could you ever vote for a woman to run your country?” Needless to say I told him not to go there, but he wouldn’t give up. He kept pushing the issue to places where I just got fed up. I mean, at the end of the day I don’t need a debate on my taxi ride, I’d really rather catch up on business emails. When he dropped me off, I let him know I wouldn’t be needing his services any more. He lost a a big sale & good amount of certain income. F for his sales strategy.


The flip side, years ago I was at a well funded start-up and we were interviewing PR firms. I was meeting with the last company, and was so impressed hired them on the spot. After telling him to shoot over a contract and other docs, I’d never seen a guy wrap up a meeting so fast! He immediately stood up, said thanks, rounded up his team and bolted out the door. I talked to him later about it, and he said “what good would it do, at any time someone could have said something to screw the deal?!”  Great point. He knew when to shut up. Great sales strategy.


Recently I was reminded of this very important lesson that should be ingrained in all of us. I was speaking with a client who was having some issues with our app – it just wasn’t fitting her needs which were very specific. We’d had a very productive call, she was happy with the fixes and the timelines. Done deal! But for some reason I got excited and and started to mention a couple of ‘stretch’ features we’d been contemplating. All it did was highlight some weaknesses in our current offering, which made her think about other features we might not have yet. Needless to say I caught myself early on, did a bit of a dance and reeled it back in. But whew! Not knowing when to shut up can cost you! When the deal is done, wrap it up.
Have you ever muffed this sales strategy and talked yourself out of a sale? Let me know your experience!

Startup Stories: Lessons Learned This Week

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.

Dasheroo's diversified sales strategy.

At Dasheroo we’re planning on diversifying our sales to different targeted audiences…are you?

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.