Career Pivoting as seen from a Twilio Sales Development Representative

A native of São Paulo, Brazil, Maia Casttro never thought that sales would be a part of her professional career goals. She was as surprised as anyone that a background in performance theater and a love for people would lead her to a promising future in sales and change her career path in many ways. It's a pivot that resulted in a genuinely positive experience as a contributing member of Segment, a leading customer data platform within Twilio.

During Twilio's recent company-wide break, which the company instituted during the pandemic to help employees rest and recharge, Maia and I chatted about her experience and her new outlook as a Sales Development Representative. What started as a unique learning opportunity has become a developing career shift, and although sales is not the easiest discipline to pivot to, Maia's experience has been seamless overall. Among other outcomes, she finds herself working alongside a supportive and encouraging team and is happy to report that Twilio truly invests in its employees and their career growth.

"Management encourages us to explore whether or not sales is for us because it's not for everyone," says Maia. They leave space for folks to speak up and express if they are interested in another team or role. They'd rather lose you to a different team than another company."

Twilio is probably best known as the world's leading cloud communication platform, enabling top brands to engage customers across channels like SMS, voice, video, WhatsApp, email, and more. While classified as a tech company, many roles within the company aren't technical positions, including Maia's role. Often, folks are intimidated by working in the tech industry and might lack the confidence to apply to roles within the space. Maia quickly pointed out that it's essential to understand where your strengths lie and apply any transferable skills to help you thrive in a sales role.

"You must be comfortable meeting new people and talking to strangers, even if you aren't super extroverted. You just have to be open to learning," she said. "Your sales approach may differ from someone else's, and that's okay. As long as you lead with enthusiasm and an open mind about the product, you might be pleasantly surprised by the outcome."

Those interested in exploring a similar position should know that there are no rules as to what the perfect sales pitch should look like or what someone in a sales role must have regarding skills. But there are two core strengths that any salesperson will benefit from: having excellent communication skills and — most importantly — being a good listener.

"Sometimes in sales, people are so worried about selling the product that they overwhelm the person they are speaking with. What I've learned in my current role is that if you allow them to speak and actually listen to them, you can get a lot more out of the call."

In addition to being a positive and productive environment for employees on all levels, Twilio's magic starts with its people. As a company that considers itself a work in progress, leadership has been actively working towards building sustainable practices that will help them identify, hire, and retain underrepresented talent. Twilio strives to foster a culture rooted in diversity, equity, and inclusion. To do this effectively, they leverage anti-racism as a framework to activate leadership, teams, and individuals behind this critical work and strive to ensure that all voices are heard and represented.

Questions & Answers with Maia Casttro:

As we continued to chat, we dug deeper into Maia's day-to-day at Twilio, why she chose to apply for a position there, and what her experience has been like as a Sales Development Representative on the Segment team.

What is your career background, and what was your journey to working at Twilio?

"I worked in finance for a while and HR, managing people. I didn't come from a sales background at all, but I did want to make a pivot and try something new, especially considering the economic position that we are currently in. A friend of mine worked at Twilio and always said such great things about the company. I applied for this role, and they took a chance on me."

What was your experience like in the beginning? What are some of the challenges you encountered?

"It was definitely a challenge because I've never had a "quota" before. It's a different kind of motivation that was new for me and initially a little scary. But Twilio has a very comprehensive training process and I felt very well prepared for what was coming. It's also great that I started with a group of new hires who were also new to sales and were all having the same experiences as you."

For readers who do not come from a tech sales background, what can you share about the product, and how important is it to know the product well?

"Honestly, on the Segment side, I think the product is super easy to talk about. It's not too complicated to explain why people need it, and the product itself is very digestible for people who might be unfamiliar with the concept. Because of this, I've had conversations with prospects who weren't immediately interested in buying but were interested in learning more. You never know when those can turn into leads."

How do you vet prospects for sales pitches?

"I usually go with individuals who are easier to talk to, like engineers and marketing professionals, because they are the ones who will be using our product the most. My goal is always to ensure my pitch isn't a high-pressure "salesy" approach, as that often makes the prospect uncomfortable and unresponsive. Instead, my objective is not to make the final sale but to get them interested in the product. Then, if they decide to move forward down the line, they might remember our conversation and interaction. I really create the initial relationship with prospects."

What is your advice for people who may not have tried sales but are looking to transition?

"There are people in my network who honestly admit that sales is not for them. But I think it's worth a try as it's a great step into the tech industry. Even if a sales position is not your ultimate goal, it's worth the effort because you'll learn other things about yourself and develop skills that can benefit you in so many other roles. And here at Twilio, you're already inside a good company with good values and strong support for internal mobility."

What tactics have worked to your advantage in engaging potential clients?

"Being interested in people is so important. Most of the time, it's just you getting them to talk and not doing all the talking yourself, which is the biggest mistake I made when I started in sales. I wanted to talk so much about the product and how great it was, but the more you get them to talk, the more natural and engaging it is."

Any advice on how to navigate Twilio?

"It's important to be proactive. At the end of the day, it's your job to do the work. Try to go after whatever you're working on before asking for help."

Interested in transforming your career?

If you are an experienced sales professional or interested in making a pivot into sales, this is probably a great start for you. Apply today!