Commercial Account Executive Arinze Obiora’s path to sales has been anything but linear. Obiora started his career in accounting, but took a detour to pursue a lifelong dream of being a professional basketball player abroad. After two years playing basketball in El Salvador and Finland, Obiora returned to the United States, where he took time to figure out his next career step.
Enter, Datadog. Despite his lack of sales experience, Obiora’s determination, grit and positive life outlook landed him a role at the monitoring and security platform for developers, where he’s been growing his career ever since. Read Obiora’s story below to learn why Datadog values salespeople with diverse backgrounds and skillsets — and how a position in sales can benefit nearly any career path.
What a Commercial Account Executive Does at Datadog
My job and goal every day is to break into commercial-sized accounts.
Everything is outbound so this is an interesting role that requires a lot of deep research before making a call. We do a lot of targeted research to hypothesize what’ll convince customers to work with Datadog. We test the hypothesis to see if it hits home, and if it doesn’t, we go back to the drawing board.
What Does Datadog Do?
Datadog is a unified monitoring and security platform for cloud environments, providing observability across infrastructure, applications, and logs.
Why Arinze Obiora Changed Careers and Moved Into Sales
When I first joined accounting, I saw the different steps it would take to get to partner, and knew it wasn’t the path I wanted. My long-term goal is to be an entrepreneur. Every job I’ve taken takes that into consideration. Even though my long-term goal hasn’t changed, my career path has shifted. All entrepreneurs have to be sellers. I didn’t know while I was applying, but the next step in my career journey was to learn how to sell.
How Arinze Obiora Built a Sales Career at Datadog
I started at KPMG in 2019 as a fresh graduate eager to get into the accounting world. I viewed accounting as the foundation of every business. I was an audit associate for about one year before getting promoted to senior associate, where I led my audit teams to the finish line during each engagement for two years. It was a very fun, task-oriented, always-on role, especially during busy seasons. But it taught me a lot about what hard work looks like and the outcome of that hard work. Working with the team sun up to sun down was always a highlight that made it enjoyable.
Eventually, I had an intern that I was training who was finishing up grad school. I was 23 and teaching him how audits work, and I asked him why he chose to get into accounting now. He said he used to be a teacher, and got the chance to travel the world teaching English in different countries, and now he was ready to start a new career journey.
It lit a fire under me. It was similar to what I wanted to do — travel and play basketball — I realized at that moment that I could always come back to accounting, but my dream to be a professional basketball player had an expiration date. So, I left accounting and pursued my dream.
I never stopped playing basketball, but I knew to get back in top shape I had to turn up the intensity and devote more time. I was burned out from the busy season, so I decided to take a three-month sabbatical. During that time I would get up at 5 a.m everyday, do hot yoga, run on the treadmill, play basketball…all to get back in game shape. One of my friends, an old college teammate, had just signed to a team and said there may be a job opportunity for me in El Salvador because the team was looking for another player.
“They’re looking for another player. Do you want a recommendation?” he asked.
I sent my name in and sent over some film from my college basketball era. When I got the call back, I decided to go for tryouts when my sabbatical ended, as the opportunity was too big to pass up. Three days later, I was in El Salvador meeting the team for tryouts, and one day after that, I had made the roster. I became a professional basketball player! I played with the team for a year before signing a contract to play in Finland for another year.
After coming back from Finland, I had an offer from another team in Ecuador, but I missed out on the opportunity and found myself in a rut. I spent that summer coaching with the Jr. Celtics Academy League, a developmental basketball program for youth, where I advocated for the kids, trained them and acted as their mentor. I enjoyed it immensely and was happy to find a new lane in basketball that involved giving back to the community that served me growing up.
After that experience, I started seeking my next chapter, but I was hitting a wall. Everyone I knew told me I was a perfect fit for sales, so I started applying to different sales jobs but I kept getting rejected. Then I found Datadog. I was able to connect with my recruiter for an unrelated role, who heard that I was interested in sales. He said, “Give me a few weeks and I’ll get back to you.” I didn’t think I would hear from him, but two weeks later he reached out and said he’d gotten me an interview with one of the sales recruiters. He did a great job getting me ready for what the sales role would entail. I brought that into my interview, had a great interview experience, and got my first job in sales with Datadog as a sales development representative.
I was a commercial SDR first, which was a wake-up call for me because I found myself in a completely new field that I didn’t study in college. I was not sure how to cold call or write emails to prospects. My first four to five months were tough. I thought I would be let go, but meeting with my manager, finding mentors and talking to peers helped immensely. Every Tuesday we had pitch practice where we practiced cold calling and demo sessions. I pieced together my talk track, put it in my own words, and that’s how I started to turn my sales career around.
How Does Datadog Support Employees With No Sales Experience?
- Recruiter support
- Manager coaching
- Pitch practice
- Peer mentorship
The SDR role, although very difficult at first, showed me that sales is not for the weak. It shaped my career, gave me a solid foundation in sales and ultimately led to my promotion to commercial account executive in June of 2025, where I am today.
How Arinze Obiora Overcame Rejection
Looking for a job, getting used to rejection and not knowing what’s next is difficult, especially after having just achieved one of my life goals of playing professional basketball. There’s so much unknown, and only so much you can do to control the outcome.
Whether you’re applying for jobs, going through the interview process, or dealing with rejection, you are improving yourself. In times like this, I end up taking everything as a learning lesson, so when the next opportunity comes around, I can be better and secure the job.
I did a lot of proactive learning, training and reaching out to people to see how I could accomplish my goal and look for my next chapter. The only way is up. Eventually, you’ll see the light and it’s that much brighter.
My outlook on life is that you can look at the glass two ways: half-full or half-empty. I’ve never seen any positive outcome from negative thinking. If you can take the negative and turn it into a positive, good will come back to you. Whenever I have dark days, I push through with positivity and determination.
Frequently Asked Questions
How does Datadog train employees with no sales background?
Datadog supports employees with no sales background through recruiter support, manager coaching, pitch practice and peer mentorship. In Arinze Obiora’s case, his recruiter helped prepare him for what the sales role would entail, and once he joined, regular meetings with his manager, mentors and peers helped him improve.
What does a sales development role at Datadog involve?
A sales development role at Datadog is outbound and focused on breaking into commercial-sized accounts. It requires deep company research before reaching out, building hypotheses about what will convince customers to work with Datadog, testing those ideas and refining the approach when needed.
What skills are needed to succeed in sales without experience?
Based on Arinze’s experience, important skills include determination, grit, positivity, openness to learning and the ability to handle rejection. Proactive learning, practice, research and being willing to seek help from managers, mentors and peers also played a key role in his success.
