This post isn't about bragging. Hell, I'm not even sure I know why I'm writing this. I just know I've been wanting to write this for awhile. This is a serious post. I wanted to write a long rant about my thoughts on sales leadership. 

If you are landing on this page because you are searching for something about sales leadership, and what makes you a good sales leader, let me tell you about my background before going into this post.

I've been playing the startup game for over a decade now.

My hair is starting to gray, the bags under my eyes seem to be a constant, and things I've witnessed and been through are Groundhog Day.  

If you don't get that reference, I'm seeing the same things over and over again. I was part of a startup success story in New Hampshire. One that saw a small company with less than 20 employees launch a B2B business, and grow it to nearly 400+ jobs.

dyn teamAbove was a good chunk of people doing Mad Men day at Dyn. We all dressed up like we were in Mad Men because we all liked Mad Men. 

There are moments in time where great people come together, and as a result, make great teams.

When you cross great people with great teams, the best things happen.

Just in the photo above alone, there are two families that were started between four coworkers, four startups, several future directors and VPs at other companies, one future cancer survivors, and many future job creators in New Hampshire. 

Sure we've all had magic for a little while, but it eventually it fades. I've been on the failing side of businesses as well. I left before Dyn got acquired. I left before the entire company's spirit was ambulated by the corporate machine that the world needs. They laid off almost all of my old colleagues last month. 

Life after Dyn wasn't so sweet for a little while. I got swindled into joining a startup as a CMO with a ton of potential, only to find out that we were selling vaporware. I co-founded another startup and watched it burn slowly over the course of a 2 years. However, the most important thing I've learned is how to pick myself back up. 

leadiq team USA photoThe LeadIQ USA team at the beginning of August. There are moments in time where great people come together, and as a result, make great teams. When you cross great people with great teams, the best things happen. 

So now that you know a little bit about me, and know I've seen both sides of the coin, I want to talk about what makes a good sales leader. This actually applies to all leaders for some these qualities. 

To start with, I think that as pretentious and snooty as I find TED Talks to be, the core thing that drives and inspires people is WHY. You probably know what link that is coming. As much as I would like to make fun of popular things like Simon Sinek, I read his book, Start With Why.

Based on my experience and the examples is his book, Simon Sinek has convinced me that he is right.

The concept that Sinek talks about here is that people don't buy what you do, they buy why you do it. Many sales leaders realize this, and inspire their troops to sell why a company is doing something. I've been aware of this at every place I've worked. I've known about the important of selling why over what for a long time. So why did companies I work for fail, while others have succeeded?  A good sales leader needs to know something else.

Great leaders inspire people with "WHY." The best sales leaders know how to make a great "why." 

If you want to be an effective sales leader, you have to gather the troops and inspire them with a good why. I see so many startups that come talk to me and get advice. They have a why, but how many sales leaders make a why that actually inspires people?

Here's an example. At Dyn, our CRO was a guy name Kyle York. He was a rep who was hired, and quickly worked his way up to be Dyn's Chief Revenue Officer.

York didn't just pick a "why" customers should buy. York helped us as reps understand why we should be working at Dyn. Why this was the right time, and why our work was important. Looking back on it, it worked well for our team. Here it is:

We believed we could be the backbone of the internet. 

Now that "why" may sound kind of like marketing speak and a little selfish. We didn't tell customers this. Let me give you the real internal longer version of this. What actually made it all mean so much more to all of us. This is what it really was saying:

We believe that a kind small company in New Hampshire, a wonderful, underrated, underdog state no one thinks about, can be the centerpiece for all these websites/apps we use in our lives everyday now and into the future. 

dyn dogThat's what I'm talking about. We had a chip on a shoulder. We weren't just cold calling and emailing to help people and collect commission checks. We were doing it to defend our home. Why not us? Why did we have to be in the Bay Area, Boston, Seattle, or Washington DC?

Why couldn't we live in this place we all love to call home? Why couldn't New Hampshire be the centerpiece of the internet, similar to how Hollywood is for the film industry?

There are three different types of WHYs that an effective sales leader needs to answer to get a team behind you. 

  1. Why is the company here for your customers? (Everyone at the company should be able to answer)
  2. Why does your sales team exist at the company? (Your whole sales team should have this narrowed down)
  3. Why are you personally here? (Individual answer)

Effective sales leaders can help uncover all these things. These were my three at Dyn that motivated me. 

  1. We believe Dyn is here to make sure the world can have the best performance and connectivity to your favorite web applications and websites (company purpose). 
  2. We believe Dyn should be the backbone of the internet, and our team is going to ensure that this happens (whole sales team's purpose).
  3. I want to be one of the best marketers in the world. I'm working here to learn business and put myself in a good position to do marketing some day (personal purpose).

The last thing you need for #2 and #3 has to focus on the importance of timing. We believed that New Hampshire had to be the backbone, but the why also had urgency because it felt like gold rush. If we didn't get companies outsourcing DNS to us soon, someone else would take the market. There is an opportunity, and only a limited amount of time to hit that goal. 

So as a sales leader, don't just find a why. Find a good why that has urgency for your team. 

That's not the only thing leaders do. On our next blog post, we'll talk about how leaders get into the trenches sometimes, and do things outside of their job descriptions. 

Posted by Ryan O'Hara
Ryan O'Hara
Ryan O'Hara has been an early employee at several startups helping them with marketing and prospecting tactics, including Dyn who was acquired by Oracle for $600+ million in 2016. He's had prospecting campaigns featured in Fortune, Mashable, and TheNextWeb. Ryan specializes in branding, business development, prospecting, and coaching people on how to make good digital first impressions. He also mentors two accelerators, The Iron Yard and The Alpha Loft, and hosts The Prospecting

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