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Written by 11:16 am entrepreneurism

Thinking Like a Cupcake Kingpin

As you know, my company ChallengeWave is a tool for healthy challenges at work. at ChallengeWave, we’ve got a number of very large prospects (VLPs) in our sales pipeline. These prospects represent many millions of dollars of revenue. Each sale is complicated and requires approval at numerous levels. Each sale also requires a significant budgetary appropriation. These factors increase the sales cycle, or the length of time it take to close the deal and start receiving funds.

Dealing with complex sales is a work of art. It requires skills in information gathering, positioning and patience. Many months pass before we get to an implementation. This is not only frustrating, but it causes delay in verifying our newest capability with users. We’ve been looking at ways to increase our feedback loop with our customers. We’ve chosen to do this by finding customers with smaller sales cycles.

Now, the good things about smaller markets is the shorter line to decision makers and budget wranglers. We can get feedback on our business much quicker. We can validate our results without going through a 9-18 month sales cycle.

This presents us with an interesting problem. As we compete with companies many times our size, our nimbleness and ability to deliver customized solutions is a large asset for us. This asset isn’t of great interest for smaller markets who may not even have a wellness strategy at all. Much less, have complicated systems to integrate with. We need to carve out a compelling, simplified offering to help small business.

Cupcake Kingpin

Getting to an understanding of this problem and defining a strategy has taken many months. When running a daily business one gets mired in details and it can be tough to see the forest for the proverbial trees. One trick I use to help me step back from details and focus on the big picture is to imagine I’m a cupcake kingpin in the cupcake business. (My years of making cupcakes for my nieces makes me an expert 🙂 ) So I ask myself, if I ran a cupcake business, how might I handle this problem?

The first thing we must do is rephrase the issues in cupcake-ese. This helps us to over-simply the details and look at the bug picture from an outsiders perspective.

My Problem in Cupcake-ese

In cupcake-ese, the problem is we have a new, unproven recipe and we need to see if people like it enough to buy it.

How would you approach this if it was your cupcake business?

  • Would you hire an army of SEO consultants to build link backs and press releases?
  • Would you hire a market research firm to ascertain which part of the Gartner Magic Quadrant you fit into?
  • Would you just discontinue your current offerings and just offer your new product to the public at large? ( Ha Ha, you may laugh at the absurdity of this, but that is what happened with New Coke in the ’80s)

My Solution In Cupcake-ese

The way to solve this problem for the cupcake business is to just make up a few batches and hand them out on the street. If people vomit in the nearest garbage can after ingesting your newest cupcake treat, your mix needs adjusting. However, if the test subjects come back with their friends, you have a winner.

So, we at ChallengeWave have a new cupcake recipe and we are looking for suckers a trial group. Group members will get 2 months of ChallengeWave for their use. Employees will be able to track their activities, challenge other employees, compete on teams and compete against other companies.

In exchange for the free service, ChallengeWave wants unvarnished feedback and help with case studies or press releases as appropriate. If you think your company might be interested in giving ChallengeWave a shot and your company is:

  • 10-50 employees
  • flexible
  • somewhat motivated (especially to change their lifestyle)
  • somewhat competitive
  • computer literate
  • team oriented

If your organization is interested in applying for a trial of ChallengeWave for your organization, let us know.


Have you considered the cupcake kingpin approach to problem solving? Have you solved problems with the cupcake (or similar) method?
Tell me about it in the comments….

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