On July 11, 2017, Fusemachines hosted “Coaching the Startup Sales Rep” as part of the monthly SalesTech event at Work-Bench.  Noah Goldman, advisor at, Stensul, and, moderated the panel. The event featured speakers Steve Richards, founder CRO of ExecVision and Kris Wiig, VP of Sales at StellaService to share their experiences and views on the topic.

About the Speakers

Steve and Kris have both spent many years working in sales and sales coaching. Steve specializes in coaching sales representatives to achieve their ultimate potential. He owns a sales technology company that aims to help executives understand their business in new ways through their original concept termed ‘Conversation Intelligence’.

Kris’ expertise lies in assisting B2B organizations to develop and execute a Go-To-Market Strategy. She helps to build, market, sell and evangelize innovative products and services tailored to a new or emerging marketing segment.

Speakers’ Take on the Current Startup Scenario

Kris spoke about the changes in sales in the startup context during the last two decades and what that means for today’s sales reps. She said “The most difficult thing about being in startup sales is that anybody can figure it out if you have enough time. However, if you don’t figure it out in time, not only do you lose your job, your time loses its job, and your company goes out of business.”

She also mentions the shift to a reality in which people are joining startups in order to experience a sense of accomplishment that is unique to that environment. Steve, talked about the science that is involved in coaching.In businesses with over 100 employees, you can implement sales enabling and essentially hire sales coaches, which he highly recommends in the light core sales being people.

Coaching Advice by Steve

Steve stated that he believes that the essence of coaching is getting people who are being coached to conclude something for themselves that they can put into action. This is a simple definition of training vs. coaching. “To be successful the sales reps have to be excited about what they are selling. In fact, a person needs to be true to themselves and then they can be taught the subject matter and expertise.” He further added.

He went on to quote Howard Diamond stating that the best sales interview question is: “What questions do you have for me?” (Given the context that they have gone through other interviews to ensure proper credentials). Additionally, he sees value in having them shadow someone else doing the job in order to observe them in their natural state.

Coaching Advice by Kris

Kris stated that as a coach you’re supposed to critique, but you need to be careful and not critique too much, which can be counterproductive. She suggested for one negative, a coach needs to provide five positives. The easiest way to do that is to continuously positively publicly praise reps in public.

She continually emphasized trust saying “The first starting point is building trust with your team.” To which Steve added that defined service level agreements (SLA), a comp plan, a clear career path, conflict avoidance, and core values are very important to building the foundation for trust. Kris added “It is not my job to figure out your career path. It is my job to help you know what you want to do in regards to sale.”

Many inexperienced young people are attracted to sales, but only some of them are happy with it. Once someone does decide they want to be in sales, it then becomes the manager’s job to help them thrive. Additionally, Kris shared an interview question that she sometimes asks “Who were the last two strangers you talked to?” The reason being that if they want to be in sales they have to be comfortable interacting and can’t be too much in their head.

Coaching Advice on Self Learning

Steve suggested to absorb everything (attend events like this, listen to podcasts, read books) He urged to take ownership of their own career development. He added “Seek out a mentor on your own. Someone who’s where you want to be in five years and find out how they got there. Don’t wait for your manager to hand it to you.”

Kris mentioned that it’s a trainable skill as there’s so many sales material out there. “Have the self-discipline to implement what you read/learn. Furthermore, have multiple mentors even if some of them are your peer or junior to you. They may know how to do something better. Just have curiosity and ask questions.” she says.

 Some Books That Are Helpful for Emerging Sales Reps

  • It’s Your Ship: Management Techniques from the Best Damn Ship in the Navy by Michael Abrashoff
  • Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers by Geoffrey Moore
  • Sales Acceleration Formula by Mark Roberge
  • Smart Calling by Art Sobczak
  • Insight Dialogue: The Interpersonal Path to Freedom by Gregory Kramer
  • The Machine by Justin Roff Marsh
  • The Joshua Principle by Tony J. Hughes


  • Be excited for what you are selling
  • Be curious and don’t be shy to ask questions
  • Learn and continue to be humble enough to say you don’t have all the answers
  • The learning of buying and selling is a never ending process
  • Do your homework and be ready for every challenge
  • Prepare yourself to have an ability to bring a real process
  • You have to build enough to support the other people that are going to come on later
  • Have the self-discipline to implement what you read/learn