How did you get your foot in the door to tech and how did you make that first transition from Tech Sales (SDR) to Ops/Enablement?

I went to Boston college. I was very wide eyed and applied to all the major tech companies thinking I would just land a job. I very quickly found out that's not how it works. 

I knew I loved California and wanted to live there. I grew up in Florida and went to school in Boston at the time and I just couldn’t do the cold weather anymore. One of my best friends was from Cupertino. So that's why I just packed the car and drove out. 

So I moved to the Bay Area after college. But when I moved to the Bay Area I had literally zero plan in terms of what my career was going to look like. 

I was working a retail job and driving for Uber for a year looking for that real opportunity. Then I stumbled upon a tech boot camp and I'll be honest I wasn't really that optimistic. I’ve heard about coding bootcamps and I thought they could be kind of slimy. 

But FlockJ, which no longer exists anymore as it used to, was a bootcamp that really focused on helping people from underserved communities get their foot into the door to tech as an SDR. And I would say relative to the other people in my cohort, I was definitely more privileged because I had a college degree. But nonetheless, I was in the group.

I did everything I could to interview and I got my foot in the door with Gong. I actually didn't realize how great of a company it was until I reflected back on it. They threw me into the enterprise space, which candidly I wasn't ready for. I don't think any bootcamp truly prepares you. You're gonna have to do all the work and really just lean in and fail fast and fail often. Less so when I was at Gong, but certainly when I moved on to my next role. On paper, it says I was a learning and development specialist, but I was really just an SDR. We were selling into the HR space, so we changed our title to give us more connects.

That said, versus Gong, my second company in tech was in a much earlier growth stage and I was one of the first SDRs to help expand their North America business. Because of that, a lot of processes didn't exist, and there was no one to truly enable us on how to use tools like SalesNav, Outreach, etc. And so I just started doing that on my own, both for myself as well as proactively sharing it out with others.

I still at that point was not thinking about going into enablement until there was a role that opened up back at Gong. I interviewed through five rounds, apparently did really well, but then they cut the budget and they told me the role doesn't exist anymore. And then that's when I serendipitously got a message from our current president of sales, Lynn Doherty, who I prospected when I was back at Gong.

And I love telling this story because it really speaks to how you never know when good first impressions are going to come back to you. So almost three years after I prospected to her, she reached out to me saying, “hey, I know you just started at this new company, but I'm moving over to Sumo Logic and I really remember how you prospected me. Would you be open to teaching our SDRs how to do the same?”

And so essentially they created the role for me. So that's why on my profile, I have operations and enablement in my title. And I think that the way that I approach enablement might be a little different than what you typically hear from other enablement folks who live in LMSs all day long and are primarily focused on building out onboarding programs.

I do that but I'm also involved with all the operation side of things. So I'm the admin for all of our tools, helping troubleshoot and optimize our tech stack as well. 

So I think that brings you up to speed with how I got my foot in the door and how I ended up in the role I'm in now.

Did you explore other career paths after SDR other than enablement & ops? 

Yes, I was looking at customer success. 

As an SDR I quickly found that I love the hustle, but I don't know if I could do that for the next 20 years as an AE. 

I innately love helping other people, So customer success was the immediate place that I looked because you can have authentic conversations within an established relationship versus having to fight to have a conversation as an SDR or even as an AE. 

The reason why I didn't end up pursuing Customer Success is because this other opportunity fell in my lap. I'd almost doubled the salary, and I was like, all right, never mind. 

What resources were really pivotal to help you in your career? 

I think what’s really been impactful has just been my own self growth outside of work altogether. 

I was a lazy college student – I didn't approach college the right way, and I really wanted to turn things around.

I had a “woe is me” moment for a good year, I would say. But I knew that ultimately that's on me to do the work, and I can't get hung up on feeling like I'm behind all the peers I went to college with. 

My main motivations at first were probably just all negative, to be honest. 

It was mainly financial. It was like, just being in debt and realizing, “all right, I got rent coming up, but I only have enough to cover two thirds of it.” 

And there was a bit of ego involved as well. Because I grew up, I was always very smart, I excelled at every sport, I was pretty good at music. And I naively thought that just means I'm going to make this work and be a musician. So it was a slap in the face. And so I think that's maybe it wasn't a singular moment, but that's what turned it around for me.

Finally, my motivations probably had something to do with my upbringing as well. My dad is a marathon runner and his mantra was “no excuses,” which wasn't necessarily helpful all the time. But I have retained that in the sense of: you always have the power to do something. Even if it's my  marginal, do something to make some progress here.

And so I'm really big on self help books. I have probably every one that exists. I don't think you're always ready for the self help book. I've had some of these books for five years and they resonate a lot more with me now than they ever did then, but even just the inspiration to buy the book probably did help just with my overall motivation and kind of belief in myself that I'm going to make this thing work one way or another.

Similarly, podcasts. So there's this one podcast called the Ritual podcast. That is my favorite podcast of all time. The host is almost 60 years old and they hold hour long discussions with pretty much anyone who is exceptional in their field and you will quickly notice there's always a common thread of just hard work ethic, open mindedness, empathy for others, and living a life of service. And all of those have helped add stability even during the times of uncertainty with my career, I still had a sense of confidence that I was on the right path growing as a person, even if I wasn't growing on paper in terms of my career. 

I had a lot of people help me but Davidson Hang is the closest that I've had to a true mentor. He mentored me out of the kindness of his heart and we've remained friends ever since. He was giving me advice especially when I just started as an SDR or even while I was interviewing for subsequent roles.