Insights | Sales

Sales Role Playing in VC Pitches

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Michael Brown

June 20, 2016
Bowery Capital

At Bowery we focus a lot on an investment’s ability to generate early sales and customer wins. We are so maniacal about it we singularly focus on helping our portfolio post-investment in this regard. Everything from systems to help entrepreneurs with prospecting, deal pipelines and customer introductions to blueprints for product pitches, customer case studies, pricing models and many other elements is really what we are all about. We literally focus on nothing else. We’ve seen a lot of pitches come through our door and one thing remains certain – the best entrepreneurs in business software have a really strong ability to articulate the value proposition and “why potential customers will care” in pitch meetings.

As a result, we have tried to focus on asking entrepreneurs in real time to role play with using us as a potential customer. Sales role playing is nothing new and any great company with a strong sales team has likely gone through more real time role playing exercises than they care to remember. Being able to answer questions like “I am a CTO of a medium sized company, why am I going to take a meeting with you?” or “I am the CMO of a Fortune 500 company, what do you do that all these other vendors don’t do?” or “I am a developer who has 100 ways to spend my $100 budget per month – why you?” or “X company already does this – I don’t understand how you are different?” is, in many cases, more important to us than walking us through a demo of your product.

Selling is one of the major elements in building any early stage business software company. In our view the outlier entrepreneurs show us clearly how, from the first sale, they are going to win customers. A clear articulation of the value proposition, the latitude to maneuver around competition and a real ability to sell a deal in any form can go a very long way to building a successful company. As a result we are more and more asking to role play to understand this in our first meetings. If you can’t convince me why your product matters in the world of vendor overload then how are you ever going to convince a prospective customer or client to purchase your product?

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