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Seven Simple Rules for Selling to Senior Executives


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Written by: James Beriker 

With every new venture-backed software-as-a-service, ad-tech or media startup that springs up in Silicon Valley or New York, there is eventually a new crop of sales people, all with fresh marketing material, lead lists, and quotas. Their job: to help the company grow into its last valuation or secure the next round of financing. Competition for business-to-business (B2B) budgets is at an all-time high and my inbox, voicemail, InMail and social media accounts are overflowing with messages from salespeople who want “just 15 minutes” of my time.

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As critical as sales is to the success of any company, particularly in the B2B segment where outcomes are determined by sales and revenue momentum, the quality of the sales function seems to be at an all-time low. 

So, in the spirit of decreasing my own pain, and the pain of others who are in the line-of-fire, the following are seven very simple best practices for selling to senior executives like me.

1- Earn the opportunity to engage with me. You probably get some credit for effort: number of emails sent; number of calls made; voicemails left; time on phone, etc. Like many executives, I receive 25+ weekly requests for my time or for a referral to someone else on our team. No matter how persistent or creative you are, you will not rise above the noise unless you establish credibility. There are only two ways to do this: (1) send me valuable data or information that is easy to consume, directly relevant to my business, and reflects your value proposition; or, (2) get an introduction from someone I know who believes my company would benefit from your product or service–even better if that person is already your customer. Do this, and you are likely to get a meeting. 

2- Prepare me for the meeting.  If you get a call or meeting, it is on you to make sure that it is productive. At least two days before, send me an agenda and an email summarizing the value proposition of your product or service for my company, how it’s differentiated and better than other offerings, and a general idea of what it would cost. If you can get a head start on helping me understand those things, we can have a real conversation. Your email should be short, customized for my business, and should include a copy of your presentation. 

3- Get to the point–and focus on the value proposition of your product or service on my business. If we’re meeting in person, arrive early to set up your presentation. If we’re meeting on the phone, make sure you are on the bridge before me and have your presentation ready to go. Please don’t bother with small talk– no need to “connect” with me on something you learned about me on LinkedIn. Briefly introduce yourself and your company, and then clearly explain to me why my company can’t live without your product or service. This is a very high bar. Any new relationship, especially if there are integration requirements, requires resources and creates overhead inside an organization. Before I agree to divert resources to you, I must believe that we can’t live without what you’re selling, i.e., that your product or service can help my company generate materially more revenue, save significant costs, or muchmore effectively compete in my market. As a senior executive, those three things–plus how I use my time and how the company deploys its resources– are the things I care about most. 

4- Do your research. You will instantly lose any credibility you earned to land the meeting if you demonstrate that you have not done your research. If the answer to your “qualifying question” is available through a little simple research, you’re done. If you’re selling me a recruiting tool and you don’t know how many jobs I have open on my public career site, you’re done. Show me you care about more than just taking me through your process– and have invested the time to understand my business and think about how your product or service meets my needs.

5- Know your product or service. The only thing worse than not doing your research about my business is not understanding your product or service inside-out. You should be able to answer any question that I ask, whether technical or related to your business, competition or market. If you don’t know your stuff–and defer to sales engineers and account managers–what value are you adding to the conversation?

6- Less talking, more listening. It is very easy to “swing into gear” once our meeting starts–fire up your PowerPoint and “take me through” your canned presentation. Getting into this comfort zone might help you get through the meeting, but you won’t get any closer to a sale. Don’t build the meeting around your presentation and sales script. Build it around what you know about my business and your thesis for why you can help–and listen for clues. Every question I ask is a reveal, an invitation to steer the discussion towards me. Shame on you if you miss it.

7- Please, don’t be a salesman.  Your biggest challenge is to convince me that you are not a salesman. In other words, even though you are an advocate, or even better, an evangelist, for your product or service, you understand that salesmanship is about conveying value, not just taking it. Educate me by providing data and insights about my business. Show me how your product or service can materially help me. But please don’t sell to me; instead, help meunderstand the value and make the decision to buy from you.

Each of the above simple rules of engagement are derived from one very basic tenet: sales is about understanding the needs of the prospect, presenting a solution that meets those needs and overcomes the risk of saying “yes.” Getting the meeting is often the hardest part–particularly in this hyper-competitive environment. If you get the meeting, don’t blow it by missing the basics. 

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