June 13, 2017

Things That Frustrate CEOs About Sales (and Marketing)

Many entrepreneurial CEOs are frustrated by sales (or the lack thereof). And, once they hire a sales resource are often frustrated even more by sales, or lack thereof. Often, these entrepreneurial CEOs come from the product side and do not have sales or sales management experience. This makes it even more challenging and more frustrating.

When hiring a (first) sales person, many entrepreneurial CEOs think that their sales problems will be solved. This is, more often than not, not at all the case. If the CEOs don’t pay close attention to sales, then sales are unlikely to improve and may, in fact, get worse.

Here are some common sales frustrations of entrepreneurial CEOs. Some of these relate to CEOs trying to sell and some relate to CEOs hiring and managing sales people. Some of these relate to sales and some relate to marketing.

  1. Not used to “not being in control” – As a person comfortable with product development, you may be used to being in Either you could build product yourself or the people working on the product worked directly for you. This means that you had some level of control on results. Sales requires cooperation from people (prospects) who are not under your control and they often do not behave the way you would like them to. This can be frustrating to people who are not used to this.
  2. Sales skills/people/leadership isn’t strong enough – If you have hired a sales person, it is likely that after the initial honeymoon period, you are not sure that these people are strong enough based on their performance. You may be disappointed in this performance.
  3. Untrained sales people/poor execution – When you watch your sales team (or person) conduct a sales call or demo, you are not satisfied that they know enough or are not doing a quality They don’t seem to get the message or believe in the product. They are easily put off by prospects who have objections that you believe can be easily countered, but they are not doing it.
  4. Subjective sales data and poor sales forecasting – You can be frustrated by, what you perceive as a lack of quality sales This manifests itself in terms of constantly missed sales forecasts. You are told that deals are going to close in a given month and they do not. Yet these deals were forecasted at 90% to 95% probability.
  5. Not enough quality opportunities – You may be frustrated by the lack of quality sales You are certain that your product is great yet the sales, and or marketing organization is simply not generating sufficient quality sales leads for your product. Most entrepreneurs are shocked at how difficult it is to generate interest in their products.
  6. Sales and Marketing don’t work together – If you are fortunate enough to have both a sales and marketing organization (or people), you can be frustrated that not only are they not on the same page with respect to messaging and generating opportunities, that these organizations blame each other for poor sales Sales claims that the messaging is not working and there are insufficient quality leads to follow up on and marketing claims that sales is not delivering the right messaging and pushing prospects through the sales funnel.

Let’s drill down a little further on these frustration categories:

  • Sales people don’t stay on message
  • Sales people chase bad deals
  • Sales people always blame lack of product functionality for lost deals
  • Sales people do not focus on ideal customers
  • Sales people don’t control the buying agenda and let buyers control the process
  • Sales people do not properly qualify opportunities
  • Sales people are unprepared for known objections
  • Sales people don’t know customer stories and case studies
  • Sales people don’t focus on buyer problems (features)
  • Sales people over-promise
  • Sales people don’t ask hard questions
  • Sales people don’t have sufficient product knowledge
  • Sales people over-estimate (or under-estimate) competition
  • Sales people don’t couple benefits with features
  • Sales people don’t prepare for risk and change objection
  • Sales people over-forecast win rate and time frame
  • Sales people bullshit away poor performance or lost deals
  • Sales people rely on discounts
  • Sales people offer prospects “free” pilots or agree to them when prospect demands them
  • Marketing does not get messaging The messaging is all over the place and distorted by marketing speak
  • Marketing focuses too much on SEO and not enough on outbound programs
  • Marketing wastes too much time and money on non-lead generation stuff
  • Marketing does not conduct proper competitive analysis
  • The website lacks clarity, consistency of messaging, appropriate calls-to-action, content to help prospects make a purchase decision

But there are solutions to “sales” challenges that crossover between the sales function and the marketing function.

To Do – Sales

  • Hire for company stage, company culture and, if possible, domain
  • Set precise performance criteria for sales people with timeframes at time of hire. Monitor regularly (monthly if not weekly). Contact Arbor Dakota for a complete checklist of potential performance metrics for sales people and sales leadership.
  • Train sales people on customer pains and customer stories, value proposition, defensible differentiation. Do not leave sales people to train themselves. It does not work. This goes way beyond product or demo training.
  • Certify sales people in key areas like messaging, customer case studies, demonstration, sales presentation, objection handling, differentiation…). This requires discipline that most organizations do not have.
  • Use a formalized sales process and track where opportunities might get stalled or lost.
  • Conduct sales forecasting by forecasted close month but then sort based on Use historical actual rates for probability of close and time to close. Track whether sales opportunities are closing in the given forecasted month and try to determine why the sales did not happen as forecasted. Beware of sales people forecasting unqualified deals and beware of natural sales attrition. These are the two leading causes of missing sales forecasts. Adjust your probabilities accordingly for future sales forecasting.
  • Compensate sales people on the right things that drive value (MRR as opposed to services, new customers, new markets….).
  • Build and use a justification toolkit to help buyers justify your solution internally to decision makers.
  • Establish a sales operation function to on-board, train and support the sales function.


To-Do – Marketing

  1. Make sure that your website has the right market messaging and the key resources that prospects will need as they go through the buying process. Remember that these needs change over time.
  2. Document ideal customer, message points, positioning and defensible differentiation.
  3. Build and use strong case Case studies are normally used to help buyers mitigate risk. They can be used as interest development content but must be properly promoted. Buyers are unlikely to simply look at case studies on your website. So, having case studies is one thing, promoting them is another.
  4. Force outbound marketing (email, webinars, eBooks, blogs…). Don’t simply rely on inbound marketing for leads.
  5. Have a thought leadership program that sells message points, not products.

Sales will always be frustrating for most organizations. But frustrations can be mitigated if proper steps are taken in advance.

For more information on how to lower your frustration with sales and how to be a better CEO, contact Arbor Dakota below. I am committed to helping CEO’s grow their great ideas into great companies.