Beyond the Number

​How I went from Completely Average SDR to Champion Sales Operations Manager

Kiyoshi Kidd, Head of Sales Ops, Ex-SDR, Big Boy Model's Avatar

Kiyoshi Kidd, Head of Sales Ops, Ex-SDR, Big Boy Model

It was the middle of winter in Buffalo when my dream company shut their local office. I had only worked there a few weeks, and they literally left me out in the cold. (Buffalo winters are no joke.) That’s how I found work as a Sales Development Representative. Luckily, it turned out the work itself was very inspiring. It inspired me to look for another job almost immediately.


Cold calling businesses is one of the hardest roles in sales. Take it from someone who worked selling cars in the winter in Buffalo. No one gives you the time of day, and you need constant drive to make adjustments on the phone. It requires a certain type of workflow, planning, and personality to really succeed. I didn’t have that personality. My performance (and paycheck) suffered, and I started browsing around for something new.

In the meantime, I kept my sanity by exploring our company’s tech stack, without even knowing much about it. The comforting part about testing content properly is that your stats are right there in your face--you can’t argue with the data. So when something is failing, even though you had a really strong feeling that it would work, you can shut it off without too much emotional scarring. (Unlike sales, which always feels personal.)

My project had a bare bones user-instance with not much operational supervision; it was basically a free-for-all. So I had full reign to play with it as much as I wanted, and if there was one thing I was good at, it was breaking things and improving them. And word spread. Soon, I became the go-to IT guy. I was like the guy everyone wanted on their new hit track, but instead of making beats and dropping sick bars, I’m on the sales floor.  

“We The Best”
 -Kiyoshi, aka DJ Khaled 

Moving from SDR to Sales Ops with no Prior Experience

So, when an opening came up on our IT team, me—the guy with no prior sales operations or IT experience, the person who thought that CRM could only stand for Club Ricky Martin—got the job.  And now, I’m officially our in-house Outreach.io Project Manager. I manage our multiple Outreach instances, our Salesforce environment and our tech stack, and I also provide consultative and operational services with Salesforce and Outreach for the clients that have their own instance but might need a little direction.

How I Did It: The Three Step Journey

Now, you’re probably wondering how this could benefit you. I mean ... “WIIFM”, right? Don’t worry--I got you. My career transition can be summarized in three clear steps:

  1. Poke it with a stick.  Get your hands dirty. Explore the deep caverns in your work that no one else looks at. Sure, you might have some workflow rules set up, triggers made, a/b testing going on, but do you know who made it and what their motivation behind the process was? Understanding motivation behind processes helps you to think of potential improvements based on their outcomes. Once you figure out why, play in the sandbox, and don’t be afraid to break some toys. We all learn better under pressure.
  2. Make your intentions known. Whenever you see opportunity (like in my case, a call for help on the IT and Ops side of the house) put yourself in the ring. You can’t get the title if you don’t step in the ring to box for it. Get out there! Show your face, take the opportunities, MAKE IT HAPPEN. No one is going to see what you are capable of if you don’t prove yourself or show it. I made sure my supervisors knew what my plans were and what I wanted to achieve.  Getting your name out there and helping with what you can is a great way to stay on top of people’s minds.
  3.  Find your Yoda. If there is one thing that I’ve learned out of this experience is that it’s important to have a leadership team and a mentor or two that care about your growth and development. They will see  something in you that you can’t. The best way to find a mentor is to be discovered, and the only way to get discovered is to follow steps one and two. If you got it, flaunt it, shake what your momma gave you, etc.

This is how I found success! What's worked for you? Hit me up in the comments! 

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