179. Sales Mastery & Storytelling at Scaling Startups (Craig Wortmann)

Craig Wortmann of Sales Engine joins Nick to discuss Sales Mastery & Storytelling at Scaling Startups. In this episode, we cover: -Craig's background and how he became involved in the early stage tech community. -You've spent a lot of time looking at how companies make this difficult transition from the scrappy, do-it-all world of "Entrepreneurial Selling" to a "Professional Selling" organization. Talk to us about what you've observed and how companies struggle in this transition. -When is the right time to transition from 'guerilla selling' to a more organized, professional process? -When we had Tae Hee Nahm on the program he talked about three different types of sales leaders at different stages of a startup. At the beginning it was a Davey Crocket- like individual, an independent explorer who will find their own path through the wilderness... then at the growth stage, Braveheart individual- someone with that warrior spirit and finally at the scale stage he looks for the Dwight Eisenhower-- someone with political savvy to align all the sales folks and move in the right direction... do you agree or disagree and how does your philosophy differ? -What do you do when a top performing salesperson won't use the tools, align with the culture or conform to processes. -How do you handle it when the product is broken... it's clear that the offering is lacking and the issue is not with sales. -How about situations where one is selling something that doesn't exist? -Storytelling... I see founders fail at this often and even I often failed in telling my story when raising Fund I. Where do most people go wrong? -What's the story canvas and how should it best be used? -You talk about how folks should think about 'capturing, distilling, and telling' the right story at the right time for the right reasons. What's your advice here? -One of the more popular things you teach at Kellogg is called the 'The Perfect Sales Meeting'. Can you talk to us about how one should think, plan and increase their sales meeting effectiveness? -Between sales meetings or when a prospect is slow to make a decision... how does one create urgency and positive momentum toward a decision?