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Is sales leadership where you really should be?

The beatdown on Sand Hill Road where I found out for myself...

· sales leadership

Not a month goes by where I don’t have one of the following conversations:

  1. A seller who’s interested in a path to leadership and wants advice on how to get there, or,
  2. A leader who’s considering a path back to sales, and worries about the perception and career path damage they may be causing themselves.

As you know, the two jobs are considerably different.

Most of the line leaders I talk to desire a path to ultimately running an entire sales organization some day. But on their path, they realize how much of the control they have over their own destiny is lost along the way.

As a seller, you have the control. You’re independent. The bulk of your results come from your own effort, fortitude and thirst for learning.

As a leader, the reality hits quickly that your success is, for the most part, dependent on others. That can be fun and exhilarating for some. For others, it can drive you mad.

And, as you move up the leadership ladder, the heat rises. Is it for you?

Ten years ago this summer, I was in the middle of my first sales leadership role, running an entire sales organization serving as the Vice President of Worldwide Sales for an initially small tech company headquartered in the Valley. I thought it was my dream to run a sales organization, but I wasn’t sure. And, as a first timer, running a team of reps who were all older than me, I wasn’t even sure I could do it.

July 3rd, 2009, in one holy sh*t moment, my perspective changed. The heat was as high as it could be for a budding tech sales leader. Due to the circumstances, our lead investors tried to break me. In that moment, I realized I could do it, I should do it, but my relationship with my leader (CEO) was the absolute key to everything - my success, our success and our sanity.

Do you want to hear the story of what happened?

  • If you want to hear about the beating on Sand Hill Road, read on... 
  • If not, scroll to the bottom for the four takeaways.
July 2nd, 2009

As mentioned above, I was the VP of Worldwide Sales for a growing Silicon Valley based technology company. We were one of the lucky ones to survive the downturn. I was running the sales organization from my home in Chicago, having just closed out the quarter.

Unfortunately, this time we had achieved just 94% of our forecast. The phone rang. It was my CEO, Michael.

“Todd, we need you to fly out today. (Our lead investor / our chairman “Bob”) needs to meet with us at their office in Menlo Park, California at 8am tomorrow (Friday). It’ll be you and me, plus Bob…and they’re bringing in a forensic sales expert. Be prepared to have every element of your sales organization, philosophy and approach dissected the entire morning.”

He wasn’t kidding.

Let’s flashback for a moment - maybe a little Pulp Fiction style:

A little over three years earlier - January 2006

I was out in Fremont, California. It was sales kickoff, and also my first week with the company. I had just shut down my sales training business, chomping at the bit to get back into the technology space. I was tasked with running sales operations, assisting in the build out of an enterprise-class sales organization. I had no direct reports. I was just working my way back into tech.

Following the day’s event, I happened to ride with Michael (the CEO) from the hotel to dinner.

“So, Todd, what’s your ultimate goal? What do you want to be doing in the next five years?”

I replied, “I ultimately want to build and run a sales organization. I have a framework, and want to help (the current VP of Sales) build this one out. I have a ton to learn, so I can’t wait to do it with (our current VP of Sales) here now.”

October 2007 (21 months later)

I was still running sales operations, and things weren’t going very well for the company. We were in the midst of what was later called the “Great Recession”. I was in Germany for a few days training a partner. My phone wasn’t finding a network, so I was unreachable. I had a terrible case of jet-lag.

It was the third night on the trip, and I had finally fallen asleep. Sure enough, at 1am Munich time (where I was...which was 4pm California time), someone was banging on my hotel room door. I woke up, found my way to the door, peered out the peephole, and saw it was our solution consultant, Mark, who was assisting me with the training. I opened the door.

I exclaimed, “Dude! I finally fell asleep. What’s going on?”

Mark replied, “It’s Michael (our CEO). He needs to talk to you right now.” He then handed me the phone.

Michael: “Todd, the board and I just let (our current head of sales) go. You ready? We think you are!”

After having a short discussion about the details, I replied to his question, “Well, there goes another night of sleep, but of course. Let’s go!”


Over the course of the next eighteen months, we turned everything around. We went from the brink of extinction all the way to 300% year-over-year growth. As a result, we managed to raise a healthy B-Round at a time when those were just starting to pick back up.

Getting a “healthy B-Round” sounds so glamorous. Don’t get me wrong, having runway to make the right investments to fully maximize your organization’s potential is great, but you’re playing with someone else’s money now - in a big way. So, the temperature around you is suddenly more intense.


Back to July 3rd, 2009

After spending hours prepping with my CEO the night before following my arrival at the hotel near Menlo Park, it was 7:45am. Michael and I arrived at the VC’s offices, and were led to a conference room is this beautiful building. Bob (the chairman / primary investor) sat next to the ‘forensic sales expert’ Mike on one side of the table. Michael nor I had ever met Mike - but it was clear he was fully qualified for the role he had that morning.

Bob started in. “Todd, we just raised a substantial investment in (your organization), and promptly missed the first quarter number. That’s a problem. As such, we have allocated the next four hours to look at every aspect of your go-to-market strategy to figure out what happened, and make sure we have the right people in place to maximize this investment.”

Oh, good. This should be fun. And fun it wasn’t.

Mike then proceeded to pummel me. Endlessly. Questioned everything five different ways. It was exhausting, and at times frustrating. We discussed every single rep in detail; their positives, their areas for improvement, the individual management style required to maximize their performance, etc. We discussed every region; the targeted accounts by geo, by vertical, by size, by pre-requisite. My CEO wasn’t allowed to provide much input unless asked directly. This was about vetting me as a sales leader.

At around 11:30am, the sales expert completed his investigation.

He looked at the Chairman, and said words that will forever be stuck in my head.

“This guy is world class.”

The euphoria of that diagnosis lasted less than ten seconds.

Bob, the Chairman, looked at Michael (my CEO). Stared at him, actually. I swear the stare Bob gave Michael will forever stay with me. It was though he was looking through him, into his soul. He then spoke, staring at Michael, but addressing me. “Todd, please leave the room. Have a seat in the lobby.”

I knew what was about to happen, and I was practically in tears about it. My CEO, who listened to me, supported me, always had my back, and gave me my first shot at sales leadership, was about to be identified as the cause of the miss. I knew it.

Twenty minutes later, Michael walked out of the conference room quietly.

“Let’s go.” Michael said.

There were no pleasantries as we walked out of the investor’s offices. Just Michael and I. He was clearly shaken.

Suddenly, one dumb joke by one of us (I don’t remember who), and the glass jar of pressure broke. We laughed like school kids - hysterically - for the next what felt like ten minutes.

That experience changed me. My confidence. My perspective on leadership. No doubt that it changed the rest of my career so far.


We quickly got things back on track. Nailed our next two quarters, and in December of 2009, I received the coveted “Stevie” American Business Award for 2009 Worldwide Vice President of the Year. After four years there, I left in 2010 to try my hand at another start up. Not long after, the business successfully exited to SAP.

The things happened that day that changed my career. Here were my four primary takeaways:

  1. Your perception and success as a leader is dependent on your relationship with your CEO: I hurt for my CEO that day. I wanted to be the best I could be for him, because he seemed to care more about me, my success and my career than even his own. That matters. Assess your relationship with your CEO. If it's not strong, neither will be your growth as a leader.
  2. Confidence and framework matters: I learned in the moment that I was pretty good at this. I was no longer some youngster who was learning on the job. I felt like I was ready for anything. I had a framework for sales leadership that served as a foundation for always being prepared. Have a leadership framework or subscribe to a methodology. It will set you apart in interviews, but make you an infinitely better sales leader.
  3. Make sure those who matter know where you’re going: That little conversation in 2006 with my CEO around my desire to ultimately run a sales organization tipped the scales in my direction when a change was required. You’ve got to build towards it. You’ve got to prove you’re making progress so when the call comes, you’re ready. But if nobody knows where you’re headed, nobody can help you get there.
  4. Taking a round isn’t all cupcakes and lollypops: When you read that a company just took a big round, the first thing I think about is, “that SVP of Sales has gotta be feelin’ it!” It gets hot quick. You better hit that first quarter post-raise!

There’s no shame in being the best individual contributor sales rep out there. You can beat any naysayers with your giant wallet. Life is too short to take a career ladder to the roof where you just want to jump right off. Find the lane you’re passionate about, and swim.

Todd Caponi is the author of the book, The Transparency Sale. He also is a keynote speaker, workshop leader and trainer as Principal and founder of Sales Melon LLC.

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