Three Basic Questions To Ask When You’re Starting To Sell

When I got his text at 11pm on a Sunday night, I knew it was urgent.  It was a founder who had just realized that he needed to fire his director of sales.  To add to the stress, this was not just one person on the sales team, this was the whole sales team... and about 10% of the company to boot.  The thing that feels like the biggest risk when founders are at a crossroads like this one isn’t the typical fears of letting someone go (will they hate me, will they fight me, etc).. but the biggest risk founders ask is “how will I replace this revenue” if a staffing change has to be made.

I have been building great sales teams for 9 years, and coaching founders through sales challenges for the past five.  I can tell you the situation above is quite common.  In fact, according to SaaStr, 70% of first time VPs of Sales get fired.  And I’m willing to bet a conversation like the one above happens every time but could be avoided.

As a mentor and sales coach, I get reminded all the time that many startup founders think of the sales process as something they will never truly understand.  They seem to think that it is vastly different from the process of developing a product. While there are plenty of differences, I like to think of the two as being similar in many ways.  When it is done correctly, sales happens through a series of rigorous experiments.  Like product development, finding a good sales process requires testing things out, seeing results, finding what works and what doesn’t.  

In order to achieve founder-driven sales, you’ll want to make sure that you’re seeking the right information along the way.  Because my wife would really appreciate founders not hitting me up so late on a school night, I’ve outlined a few questions below that you should ask yourself before calling me in the middle of the night for advice.

Who is Going to Buy My Stuff?


Image Credit: Wikimedia

Image Credit: Wikimedia

If you’re the founder of a startup, you probably started thinking about this while (or even before) you were building your product.  In order to sell your product, after all, you have to develop an idea of who needs it.  

In my eyes, it’s important to consider not only the companies that you’re building for, but which roles are you building for.  In other words, who at the company is going to use your product?  Keep in mind, here, that you won’t always be selling directly to the end-user of the product.  You may be selling to someone who buys on behalf of another person.  While you may, in some cases, sell your product to the VP of Sales that will be using it themselves, you might also find yourself selling to a Head of IT who wants their whole team to use it.  Having an idea of who the end-user of your product is will give you an idea of who you want to get in touch with.  

You should also be asking yourself other questions like “Who has the money to buy my product?” and “Where (geographically speaking) do I want to sell this thing?”  As an early startup founder, do yourself a favor and don’t make the entire human population your target market.  Hone in on specific customers and figure out how to reach them.

Example of  prospecting on LinkedIn  by skill. Here, I've searched "e-commerce", but you should use the term that best suits your prospecting needs. 

Example of prospecting on LinkedIn by skill. Here, I've searched "e-commerce", but you should use the term that best suits your prospecting needs. 

But… How Do I Find These People?


A natural next question after you’ve defined your target buyer and user is “where will I find them?”  And a lot of people will tell you that scraping LinkedIn is a good way to start prospecting.  While it is true that there are a ton of people on LinkedIn, you want to be careful as to how you find people on LinkedIn.  For example, you never want to simply find your competitor and go after all of their clients.  Whenever people approach sales with this technique, I think of them like a moose moving through the woods.  For those of you who’ve come across a moose in the wilderness, you’ll know that you can hear it and feel it coming before you see it.  You don’t want your competitors to think of you this way. 

Instead, use LinkedIn to find other enthusiasts that might be able to use your product.  I like to do this by finding people who’ve listed skills relevant to my product on their profile.  Clicking the skill on their profile will bring you to a page which lists the thousands of people on LinkedIn that also have that skill.  As a founder, you want to recognize that this is a page of people who all potentially have problems your product could solve. 

Luckily, LinkedIn makes your job easier by listing your direct connections and secondary connections first.  At this point, you can scan through and make a list of people you either want to cold email or ask for introductions to. 

Now What?  How Do I Connect With These People?

You’re going to have to start doing some cold emailing.  If you’ve ever sent out a cold email (or received one), you already know that it’s a tough gig.  People are busy, after all.  Who has time to be responding (or even reading) cold emails?  

For this reason, you want to make sure that you write your emails in a way that lets the recipient know you’re not wasting their time.  You’ve already done your research by finding them on LinkedIn and considering the problems that they probably face in their work, so it is important to show them that. Tell them how you found them, why you’re reaching out  and what you can do to help. This is your opportunity to show the recipient you’re an expert in the field and help to establish a relationship with that person from the outset.  

While you want to experiment with cold emails and record which ones produce the best results, make sure that you’re always keeping them concise and to the point.  

Closing Tip:  Always Ask Questions

Because you’re just starting to experiment with your sales process, you want to make sure that you find out as much as you can about what you’re doing right and what you’re doing wrong.  If, for example, you are ever introduced to a secondary connect that had been ignoring your cold emails for a while, feel free to ask them why they didn’t respond.  Don’t be aggressive or anything like that, but asking someone what you did wrong and what prevented them from emailing you back will give you an idea of how to move forward with sales in the future.  

Ryan Williams