Lesson #2 – Sales Reps – The Changing of the Guard

My thoughts on Sales Staffing has less to do with anything in the book and more to do with my experience.  Interested in your comments, thoughts, experiences as it relates to Sales staff.

Like many functional areas in your business as your market matures and as you are crossing the chasm the skillsets of your employees will need to change.  Sales is a bigger challenge than most due to the Rock star culture and image that good sales folks earn and carry with them.

In the early days as you are trying to sell your product, service, solution one of the biggest jobs your sales rep has is to convince your customers that they need something that they don’t even realize that they need.  This is NOT easy and takes a patient yet persistent sales rep that is prepared to invest the time and build a really trusted relationship over a frustratingly prolonged period of time.  After they have done this they still need to be a more traditional sales rep and manage a process and close.  This is more of a patient farmer personality than a pure Type A aggressive sale type personality.

Now the problem.

The person who is successful at doing this and who closes absolutely critical sales for your business in its early critical days is more than likely NOT the right person to be selling as and  after you cross into a more mature selling environment.

As the market for your solution matures people start to understand that they do in fact need what you are selling.  They are probably building RFP’s to address those needs and you probably have more competitors than you have ever had since inception.  The main task for the Sales Rep now is not to convince prospects that they need what you sell but rather it is to be a trusted advisor of the prospects and to aggressively, competitively outsell the competition.

It is hard to change the horses that brought you!  As Jim Collins has taught us though it is critical that we have the right people on the bus and as difficult a change as this can be it is imperative that you make it.  Given the breadth of experience, history and knowledge that the original sales rep has it is often advisable to try to find a position within the company for them BUT I am NOT a fan of making up positions for people.  If the original Sales Rep wants to sell it may be best for you and for them if they can go find another company that is in a market still in its infancy and repeat their success their.

As you recruit for your new sales rep profile there are some considerations and this is where I am really interested in other experiences because there are a couple trains of thoughts but the main crux of the argument is…what is more important domain knowledge or pure sales skills.  If you sell a solution around physical asset performance do you NEED to have someone with specific knowledge and contacts and background in that space OR are you better off going and finding the best pure sales person around regardless of what they sold???

There are definite arguments for both but I tend to prioritize the must haves in this order:

  1. Industry/vertical experience – given you need to be on the front end of RFP’s and you need to have trusted relationships to successfully close deals I think having existing relationships in your target vertical or geography are critical because you may not have time to build them in a mature market.
  2. Pure sales skills – demonstrable experience that you have sold over quota consistently in your past and you can walk through and articulate, debate with me and convince me that you are a rock star.
  3. Functional/domain expertise – I rated this last because there are numerous other areas in the company where this type of support can come from if the candidate has #1 and #2 above

Love to hear your thoughts and experiences and what has worked for you??

Crossing The Chasm – Lesson#1 – Marketing In The Early Days

Where Do We Start??

Initial Assumptions:

  1. I’m going to assume you have a business concept, a strategy, some funding (bootstrapped or otherwise) and a product in some stage of development.  You may have some customers or you may be looking for your first but you are fairly early on in your company’s life but perhaps beyond pure start-up.

  2. I am writing from a B2B perspective but most of this is applicable to all businesses.

  3. While Crossing The Chasm ("CTC") focuses mostly on marketing and selling I will touch on product planning and development as well.

  4. Lastly, I will assume you have read the book and are familiar with the concepts without reviewing and reiterating the great teachings in the book.

Given you can see as clear as day how you are able to solve some of businesses biggest problems and help them save or generate huge amounts of dollars it is only fair to assume that someone closer to that business (the customer) will see your solution as the answer to all their prayers, right?  WRONG. 

Education is one of the single biggest portions of  a sales cycle in the early days.  In most cases you are trying to sell them something that they don’t even recognize that they need yet.  I know in my situation we spent countless hours and dollars trying to educate prospects on the basic NEED for what we do.  We also spent untold amounts trying to build awareness and lead generation marketing campaigns through the years.  In hindsight I would have ENTIRELY cut out these programs.  Money is tight and intuitively you think getting your message out to the masses will build brand awareness and will mass educate the market on your fantastic approach to solving their problems.


If I had to do it again (and by that I mean, the next time I do this) I would spend all those efforts on tracking and speaking to established bleeding edge early adopters within the target verticals/customers that have the most strategic value to me as a reference.  Finding bleeding edge early adopters should be the single focus of marketing efforts.   I want to be clear that when I say target early adopters I am talking about PEOPLE NOT COMPANIESPeople lead the early adoption of new technology.  Yes Corporate culture and willingness to take on these types of projects is important but in my experience, even in a let’s say less than progressive industry or company, you can and MUST find people who are visionaries and those are the people you need to market and sell to.  Seems pretty logical but tactically how do you execute against this?  Here’s my lesson’s learned for your consideration:

  1. Regardless of the type of solution you are offering and the functional area of the organization your solution is applicable to it is usually easier to find someone in the IT group than on the business side simply because of their background.  This person will be your sponsor, your advocate and it is important that in the early days you really view them as a Partner more than a Client.  Many of these people can be found using bleeding edge technologies as that is their disposition, so social media tools, SXSW type events is where they will be hanging out to try to get info about the newest and shiniest things happening in their world.
  2. Look for companies that have already crossed the chasm selling into the general space you are in and reach out to them.  They will have lessons learned that will be as and more valuable than what I am telling you here.  The most important thing they will have is the name of PEOPLE that they dealt with at the companies they sold into.  Early adopters typically don’t change, even when unsuccessful.  Finding a person inside a target company that sponsored/led/bought another visionary offering was critical to our success.  This is the person you need to contact, court, and convince that you can help them.  They will understand more than anyone else the problem you are solving and the evolutionary way in which you are going about solving it.
  3. As you look into your target industry for ideal strategic candidates, in my experience the ones who are most likely to be open to your message as Company’s are the ones who are in the Top 20% of the industry and the ones who are in the bottom 20% of the industry.  The top 20% are there for a reason and have a couple things that are very important to you as you look to sell/partner with someone.  First, they probably have access to cash more readily than weaker companies in the space and second they also have an interest in staying ahead of everyone in their space and are willing to invest in new technologies that will continue to push their performance and create further distance between them and the middle class in the industry.  Bleeding edge people are attracted to these types of companies and are given more flexibility to thrive in this type of an environment.  Companies in the bottom 20% come at it from the opposite end but are viable for a different reason.  Finding a bleeding edge person is harder (but not impossible) in these companies but the culture of the company is more open to leading edge change because in many cases they have fallen so far behind the industry leaders they know that they need some game changers to get back in the game and in a lot of cases they have tried all the “non-evolutionary” solutions available to them with little or no effect.  Both of these are good customers for different reasons which I will get into in another post when I talk about “Sales In The Early Days”.  The middle performing companies are much harder to get into when Crossing because the risk of them investing in something new and having it fail from a personal perspective is very high.  The company is performing OK and often the culture of (the risk of) failure in a mediocre company does not support individuals stepping out and taking risks where in successful companies this risk taking and failure potential is accepted and frankly expected!



Agree, Disagree, please share your experiences.

Crossing the Chasm – The "Lessons Learned" Series

For starters, if you have not yet read “Crossing the Chasm” by Geoffrey Moore please beg, borrow, steal or buy (link attached) a copy and read through it. This book is one (of the two) most influential books that I have read in my time in small technologies companies.
Crossing the Chasm is a book about the journey, the trials and the tribulations in taking your product and company from one where every sale is a missionary sale to a place where there is a broader market acceptance of what you do and the business need to solve the problem that your product solves. The transition from one side to the other requires different approaches to almost everything you do as a business. In this series of posts I will walk through each of the functional areas in a business and the external influences on each and from my experience what worked and what did not work. For most businesses despite the brilliant guidance provided by Geoffrey Moore, this trip is one riddled with trial and error. Like anything not everything will work for everyone but in this series of posts I’d like to provide what I learned and where I failed in and effort to assist others in completing a journey that many (some may say most) companies never actually complete.
Follow along as I hope I am able to provide you with insight and the ability to avoid the 1 misstep that prevents you from Crossing. If you agree, disagree, have additional stories, thoughts please add in the comments so others who read can learn from all of us as much as possible.
Let the journey begin…if there are specific areas, topics you want me to cover please let me know. Hope you enjoy.