Why I Created Skaled - Part One

Part One: Why CEOs need to support their sales leaders the same way they support marketing, product and other groups

I recently re-watched Simon Sinek’s Ted talk where he talked about successful companies having meaningful answers to why they’re doing what they’re doing, and it inspired me to think about my own “why” — why do I do what I do on a daily basis? We’ve all asked ourselves this question and probably have been torn between continuing on a familiar path or forging a new one. My “why” doesn’t revolve around making more money, there are probably simpler ways to get there instead of starting a company. My reasons are what get me out of bed and have me excited to face a new day full of opportunities to help other CEOs and sales leaders thrive. Therefore, I thought it was important for me to share why I started Skaled and hopefully this resonates on a personal and a professional level with those of you going through the struggle now.  

My First “Why?” Part one of two

Reason #1: I love to fix things and the way CEOs and other executives support sales is not working.

I saw the trap that companies kept falling into where they hired and fired Sales VPs and wondered – why does this keep happening?

Why do we outgrow this one role so quickly, and almost endlessly, but we don’t seem to have the need to replace other roles as quickly? Why does this massive mistake continue to set companies back months and years, causing huge turmoil internally through each phase of growth, and even into maturity when they go public?

Early on it is because most executives know very little about what it takes to build a scalable sales organization so they outsource it. They outsource it to an internal hire actually, a VP of Sales, and say “please get this off my plate.” And then, they get upset after a certain period because the ship they left alone for months-on-end doesn’t fit what they thought it should be. This leads to the VP of Sales being fired, or he/she quits. Then the next person comes in and has to be an improvement over the last guy, so he or she make it a little longer until the CEO realizes that the first person wasn’t that bad. Still, something else is needed, and this person ends up in the same boat — fired or resigned. This happens again and again every two to three years.

Fast forward to later stage companies with increased board and external pressures, where sales leadership is held to such high standards that they can’t admit they don’t know everything. Sales leaders are forced to trek through new territories alone with little to no help from the rest of the team, or from outside the company. Most think, “CROs/VPs of Sales are the highest paid people in the company, so they should be able to figure it out on their own, right?” Bullshit. The world of sales is evolving so rapidly that it’s impossible for heads of sales to know everything. Instead of encouraging them to get outside support (marketing, for example, spends millions on marketing agencies at most companies), sales executives are left to trudge through the unknown. If they get lucky then they are heros, and if they turn left instead of right, they are scapegoated.

Why do other groups like marketing, operations teams, IT, engineering and finance get to work with outside firms for specialized support, but sales leadership is only allowed some basic training and shoestring budgets? I strongly believe that it goes back to a subconscious resentment in many company leaders due the the fact that sales execs make so much money.

Who wants to help those guys? Let them fail, that’s why they get paid the big bucks!

I think sales leaders and companies deserve better and that’s why I started Skaled. Most sales leaders and CEOs are competent people and they just need a little help. I started Skaled because I wanted to help these VPs of Sales and CEOs make it through those scaling, challenging times in a company’s lifecycle, with as little disruption as possible.

It’s not the only reason, although a main driver, so happy to catch up with anyone going through these challenges. Next week, I’ll follow up with another post where I talk about the second reason: my love for sales. I’ll discuss why I love sales, closing sweet deals, and how that process has changed overtime. It has never been a more exciting time to be in sales as an executive or frontline person. It’s the next 5-10 years of what that means that excites me the most. 

Jake Dunlap is the CEO & Founder of Skaled, which helps b2b companies generate more meetings and close more deals. As a C-level sales leader and entrepreneur with more than a decade of experience, he has developed and led high-performing sales and operational functions for both global 2000 organizations and start-ups, specializing in building out repeatable, sustainable processes. Since launching Skaled in 2013, Jake has been a highly sought-after industry thought leader, quoted by Forbes, Inc., Huffington Post and Venture Beat.