Morgan Shelly is a former teacher and boxing instructor turned sales enthusiast. Morgan started her sales career in 2020 as an SDR and was quickly promoted to Senior SDR & Team Lead, then SDR Manager at Flexport before transitioning into her first AE role at Tray.io.
Morgan recently joined Deel as an Account Executive (and is loving it). She also moonlights as an empowering Career Coach to help her clients secure a new job, build their personal brand, transition careers, improve their work/life balance, navigate difficult situations, and more.
You used to be a teacher. How and why did you make the switch to sales? When did you know that it would be your career?
Transitioning from education to a career in sales was terrifying, intimidating, humbling, but ultimately, the best decision I’ve ever made.
After a lot of self-reflection and soul searching, I decided to quit my teaching job, moved to Argentina and traveled through South America. After I returned to the states, I applied for hundreds of sales-related roles all over the country. I was faced with countless rejection emails, so making the career switch required insane persistence.
While I adored my students, I felt like I was treading water in a broken system. I found the profession lacked the professional fulfillment I craved. I chose to pursue a career in sales specifically because I thrive in environments where I can solve problems and collaborate with diverse (adult) perspectives to drive impact. I relish in exceeding expectations on clear short-term goals (aka monthly or quarterly quota). Plus, while working as Lead Sales Consultant at TITLE Boxing Club, I was #1 out of 150 franchise locations in the 2019 Black Friday Sale, which, to me, was the confirmation that “I could do this”.
I struggled with self-doubt and imposter syndrome during my first few months in sales, especially since I was involuntarily laid off from my first sales role after 6 short weeks due to COVID, but I refused to fail. After 3 months into my SDR role at Flexport, I was convinced that I loved sales and had found my true calling.
How did being a teacher and/or boxing instructor help prepare you for a career in sales? Are there any lessons you’ve carried over that help you in your day-to-day?
In July 2022, I wrote a LinkedIn article, HOT TAKE: Teachers make the best sales reps, that highlights 10 transferable skills that contributed to my success in sales. I’m frequently reminded of how the lessons learned from my prior experience as a teacher play a vital role in my day-to-day life now.
I wouldn’t say that my former experience as a boxing instructor necessarily prepared me for a career in sales, but rather, plays an integral part of who I am. My energy, coaching style, and determination during challenging situations are all core components that I enthusiastically bring to a boxing class, a team sync, or a discovery call. In a recent professional development training, the question: “How do you want to make people feel?” resonated with me. Just like when I was instructing on a jab-cross-hook combo in a 5:45 AM boxing class, I hope to make my colleagues and clients in my sales career feel empowered, confident, understood, accepted, valued, and special.
How does selling HR software compare to selling logistics software or task automation software?
I love learning (*insert cliché teacher joke here*) and I believe gaining a deep understanding of diverse buyer personas, business challenges, pain points, and industries has helped me become an agile seller with an expanded “toolbox” of selling skills.
Selling HR-tech/Fintech to assist with onboarding, managing, and paying international workforces is exciting because the solutions that Deel offers affect individuals in a very real way, thus uncovering an inherent “human element” within the sale.
I found selling automation & integration software in the iPaaS space to be a technical and extensive selling process with a 2-week Proof of Value (POV) evaluation.
Working in sales for a freight forwarder differed from my other two roles because the sale involved physically moving goods from point A to point B.
What does a typical work day look like for you? Walk us through it.
Every day looks different in sales, especially when you can work remotely. Whether I’m working at home, at a coffee shop, or at a WeWork, my days consist of prospecting, first demo calls, creating Mutual Action Plans, LinkedIn messages, and since I’m still ramping at Deel, I try to include some continued development. After work, I usually hit up a workout class on Classpass, have a career coaching client call, or meet friends for happy hour.
What's the one thing you’ve found that helps you be successful in sales?
I don’t believe there is one single thing or some magic formula for success in a sales career, because success requires constant agility and adaptability to industry ebbs and flows, product innovation, and the unique needs of each buyer. However, I believe exceptional time management and organization skills can be a determining factor that sets a good rep apart from a great one.
What are your long term career goals? Early retirement or future CRO?
Eventually, I would love to work full-time as a sales consultant. Helping companies improve sales processes, build an outbound team from scratch, or offering speciality coaching across the sales organization for short periods of time excites me. The ability to “get in and get out” seems like the ideal situation for me because it allows me to focus deeply on a project for a few weeks or months, demonstrate significant impact, and continue to expand my network, while also avoiding the inevitable bureaucracy that exists within companies.