Breaking into Tech & Rev Ops: Getting to Somewhere I Didn’t Know I Was Going

Where am I and how the hell did I get here?? I'm starting a new role running RevOps for a super exciting fintech company tomorrow and I couldn't help but reminisce as I take this next step forward in my career.

Truthfully, I never expected to be in Revenue Operations.? I never expected to be in tech.? I never expected to leave the sports industry.? A lot of people from my previous industry ask me how to break into Tech.? Here’s my story and some guidance and tricks I used to make the jump.

The Backstory

I went into college expecting to be a baseball broadcaster. I had been writing for the Boston Red Sox for several years, I had a phenomenal portfolio of interviews with Red Sox players, celebrities, and stories of the 2000s Red Sox on-field success.? After one communications class at Elon University, I realized “this ain’t it.” I didn’t want to be calling single-A baseball in Greeneville, South Carolina making $25k.? I pivoted to business intent on coming out and working for the Red Sox - in what manner or function I had no idea.? After college, I spent one summer writing the public address scripts for the Red Sox home games - a position that made me feel very cool but wasn’t exactly a career path.? After that season, I took a chance.? And the Red Sox took a chance on me.? I applied for a position on the newly created Inside Sales team for which I was highly recommended by my manager at the time. I absolutely botched the roleplay.? I think the feedback was “that wasn’t good but why don’t you read up more on sales and we’ll try again.”? I was given a second chance, did some reading on sales fundamentals, and squeaked by with a passing grade on the next interview and they hired me.? Once I was trained up - I was pretty good.? I could walk that ballpark blindfolded and was able to sell the hell out of every seat in that ballpark.? Okay - the ones down the first baseline that face centerfield were a tough sell.? “You’re close to the action - a lot of foul balls! (even if you walk away from every game with a crick in your neck).

I spent 2 years with the Red Sox Inside Sales team and then was approached by Madison Square Garden to join their Group Sales team.? This was a step up and more of a relationship sale - so not a pound-the-phones kind of selling.? At least it started that way.? The new EVP was an old-school military boiler room my way or the highway kind of guy who wanted high volume.? It wasn’t what I wanted.? A year later, my mom unexpectedly passed away.? It was the hardest thing I’ve ever had to deal with.? I went back to work a week later seeking normalcy and a distraction.? I found I just couldn’t hit the phones and put on this rosy voice and positive attitude.? I was miserable.? I went to my VP and told her I was close to my breaking point and explained the situation.? She needed someone to do “Sales Operations” work and fought for a role to be created.? I took a biggggg pay cut.? I felt lost - I had left sales, didn’t know the operations world, barely knew Excel and now was building this position.? In truth, my role was more of an Operations Coordinator than a true Sales Operations role.

I took Excel courses to level up and eventually started doing some light reporting and data analysis.? The data wasn’t great but it provided info for my VP that she had no insight into before.? I built strong relationships with my VP and one of the Directors on the team.? I started to look for roles in tech as a Data Analyst - not knowing that there’s more to that role than vlookups and sumifs.? The job search was off to a rough start.? I looked at roles in Sales Operations and found some similarities that I could speak to and around which I could shape my resume but there were definite gaps in my resume based on the JDs in which I was interested in. This was apparent from the JD and from the few interviews I got through the spray-and-pray approach.??

Fill the Gaps

Okay, I knew how to do some Excel functions through the Excel course I took when I started in “Sales Operations” at MSG.? But there were some serious gaps that I knew would prevent me from making the jump into tech and into Sales Operations.? The gaps were a lack of any real understanding of data analysis and a lack of BI experience. I couldn’t get any of that info or experience within my current department.? I took my savings and enrolled in an in-person “Data Analysis boot camp.”? This course provided a true understanding of how to use Excel, Tableau, and SQL as a data analyst.? I learned the tools, but more importantly, I learned how to approach data like an analyst.? This didn’t just give me the skillset I would need to make the jump.? It gave me a really impressive talking point to speak to in interviews.??

I started applying the Excel work to my data analysis at MSG and really built out a reporting structure to find trends and gauge rep performance and activity.? I had leveled up.

The Direct Outreach

I was applying like crazy to Sales Operations roles and was getting zero bites.? My roommate at the time gave me a piece of advice that changed my perspective and my career.? “Check your ego at the door and reach out to the hiring manager.? If 100 people apply, maybe 10% will reach out to the hiring manager directly. That will put you in the top 10%” The last 3 jobs I took, I got through direct reach out.? In fact, this worked so well for me that I’ve often found myself in multiple late-stage convos where I’ve been able to pick and choose.? I’ll go on LinkedIn, search for the higher title in the function using a LinkedIn Sales Navigator license, and send some form of the following note:

Dear Judy,?

I hope this message finds you well. I recently applied online for the Sales Operations Manager position and wanted to reach out to further express my interest in the position. Over the past five years, I have been a foundational member of Sales/RevOps at rapidly scaling B2B SaaS start-ups. In these roles, I have spearheaded the analysis of key GTM metrics to ensure informed decision-making, managed the full GTM tech stack, and led the continuous optimization of revenue processes, maximizing effectiveness and efficiency. I am confident that this experience and skill set make me a strong fit for the role.?

Could you forward my resume to whoever is managing this search? Any direction would be greatly appreciated. I've attached my resume for your convenience.

Best,

The Resume Cheatsheet

I had no idea how helpful my sales experience would be professionally after leaving the function.? My Director at MSG helped me sell the shit out of myself in my resume and made a comparison I had never considered.? Every interview is a sales call.? The recruiter and the hiring manager are likely talking to a hefty pool of applicants.? How can I make myself stand out with minimal Sales Operations experience?

Before the days of ChatGPT and the like, I had no idea about resume optimization.? I just knew I had to have a strong resume that drew parallels from my current role to a true Sales Operations role.? With the help of my Director, Kemyell, we built a strong resume and sold the shit out of me.? I am indebted to her for her help on this and for helping shape the way I think about my resume bullet points. ? Get you a Kemyell.

With the LinkedIn direct outreach approach, I was getting interviews.? I wasn’t always able to draw simple parallels to the job I was interviewing for and I faced a ton of rejection which was really demoralizing.? One thing would change this.? I started to print out the JD, print out my resume, and write the comparison of something I was doing currently that was on the JD (even if it was sometimes a loose comparison) directly on my resume.? But writing down those notes got me through to second rounds more often than not.??

Building Your Narrative

Once I put in enough time speaking to the points on my resume and drawing parallels, I understand my narrative.? I understood how my current experience compared to the jobs I was applying for and how to further speak to each bullet point as if the roles were almost the same.? Understanding your narrative means understanding the story of who you are professionally, what you’ve been doing professionally, and how that compares to the job to which you’re applying and interviewing. With enough at-bats, it becomes easier and easier to speak to.

The Interview Sales Call

Every interview is a sales call.? Whether you’re applying to be a cashier at CVS or the CFO of CVS.? The odds are someone will almost always be a better fit than you.? You need to make yourself a better fit for them. Why should they hire you?? Because of my sales experience, I present well.? I started treating my interviews like I had treated my sales calls in the past.? I drew out feedback at the end of every interview with the question “Is there anything on my resume or that we’ve chatted through that gives you hesitation about my qualifications for the role that I can address? These people weren’t giving me interview feedback. I was getting sales objections.? The ones I was hearing were lack of experience in tech, lack of experience with BI tools and hardcore data analysis.? Having found those gaps, as mentioned above, I was now able to overcome those objections with “I’m actually about to complete my data analytics boot camp and while I haven’t done BI in a professional setting, I’m very confident I can use my experience and hit the ground running” and “while MSG certainly isn’t a true B2B Enterprise sale, I’m often working directly with businesses who similarly to the tech world, are solving a problem - how to entertain their clients/prospects and keep their employees happy.? Tough sell but when it worked, it could be an enterprise-level sale monetarily.

If you don’t have sales experience, I highly recommend doing some light research to hone some sales skills as it will be a game changer for you both in interviews and overall professionally.

Getting One Person to Take the Chance

All you need is one person.? One hiring manager to like you.? Maybe they like your resume, maybe they like how you carry yourself, maybe they like your initiative.? Looking back, I know how I was able to make the jump into tech based on this person’s feedback. I got one person to like me.? My experience was fine - I’m confident it was no better than most applicants.? I took initiative - I had sent him the note listed above which he appreciated, I was hungry and willing to do what it takes to get the job done, as evidenced by me self-financing a data analytics boot camp.? I sent him a thank you note after the interview. I was blown away to learn that 1 - not all people do this for jobs they want, and 2 - that it really makes a difference.? This guy and I were going to be a team of 2.? He wanted someone who could roll up their sleeves and get shit done. He wanted someone who could learn, but I think most importantly, he wanted someone who would be a good teammate. On a team of 2, I didn’t realize how important that was at the time.??

Until recently, my experience rarely got me interviews. ? My initiative in reaching out to the hiring manager, my initiative in professional development, and my roll-up-my-sleeves attitude got me interviews.? And then a working process to draw parallels to the job I was interviewing for and treating those interviews like a sales call allowed me to have more good interviews than bad ones. Truthfully, it’s often a numbers game.? But with the right steps, you increase your odds and make your own luck.?

Onward and Upward

This isn’t just Revenue Operations advice.? This is advice for anyone trying to move the ball forward for themselves professionally.? This applies to almost anything in tech, or in corporate in general.? This is how you play the game and win.? In sales, we often said “proven process, predictable results.” Give it a shot, build out your version of this process.? The more at-bats the better you’ll get.? I’d say I get interviews for 40-50% of the jobs I apply to with this method. In baseball, if you get a hit 30% of the time you’re batting .300 and a surefire all-star.? Use this process and I bet you’ll bat .350 and feel like the MVP.