In this #BehindTheBuilder post, Stefany shares how her Segment-to-Twilio journey has been fueled by bold leadership and a people-first approach. As a Sales leader, she’s built a culture of trust and collaboration while bringing purpose and positive energy to her team.

Behind the Builder:  Stefany Millstein, Director of Sales, Commercial

Let’s rewind to the beginning — how did your Twilio story begin, Stefany? 🎬 

I’m currently a Director of Commercial Sales focused on Twilio Segment’s Customer Data Platform (CDP). I’ve been with the company over seven years, starting at Segment in 2018 and transitioning to Twilio through their acquisition of Segment in 2020.

What first drew me to Segment was the incredible team, the powerful technology, and the meaningful problems they were tackling. Everyone I met was smart, driven, and humble — and they shared a real passion for tackling complex customer challenges.  There was also an undeniable energy around the product. Customers loved it, and that made it such an exciting place to be. 

When Twilio acquired Segment, the transition felt like a natural fit. The alignment in values, mission, and our obsession with customer success made it an easy and inspiring next chapter.

Twilio is built by builders for builders — what’s something you’ve built that makes you proud? 🔧

While I’ve had the chance to work on many exciting projects with customers I really admired during my time as an Account Executive, the thing I’m most proud of is the team I’ve helped build.

Hiring and mentoring incredible people — and then watching them sharpen their sales skills, move into more strategic roles, or step into leadership themselves has been more fulfilling than any single deal win. Helping others grow and succeed has truly been the most meaningful part of my time here.

What do you value most about the way your team works together? ​​🤝 💡

Our team has a really unique energy and a collaborative spirit that’s stayed consistent, even through a lot of change. We’re fiercely competitive and goal-oriented, but we’re just as quick to support each other and celebrate every win, big or small.

At the heart of it, our culture is built on respect, generosity, curiosity, authenticity, and a shared love of learning from one another.

How has working for a remote-first company changed how you build relationships at Twilio? 🌍 💻

Remote-first work definitely has its challenges, but I’ve found it incredibly rewarding. It’s opened the door to more personal, human connections with both teammates and customers — whether that’s meeting someone’s kids or pets on Zoom, or getting a quick glimpse into their home life.

It’s those little moments that remind us we’re all people first, and I really appreciate how much that humanizes our work. And I’ll be honest — I don’t miss the mad dash for an open conference room one bit!

What’s a Twilio event or tradition that brings your team together and recharges your energy? 🎉 ⚡

While I really value the flexibility of remote work, I especially appreciate the in-person moments Twilio creates for us to connect. Whether it’s a Sales Kickoff, SIGNAL — our customer and developer conference, regional customer events, or just casual team meetups, these gatherings give us a chance to deepen relationships, align face-to-face, and recharge our collective energy.

Tell us about a challenge at Twilio that helped you grow in unexpected ways. 🌱

Stepping back into a leadership role during the pandemic, and doing it remotely, really pushed me to be both creative and adaptable. We were navigating major shifts in the business model, and working through all of that in such a dynamic environment required a new level of agility.

What’s most rewarding is that many of the systems and processes we built during that time are not only still in place, but they’re central to how we operate and why we continue to succeed today.

Which Twilio Magic value do you carry with you every day — like your favorite hoodie or a go-to playlist?  🎧

"We Are Positrons" is the Twilio Magic value that resonates most with me. It speaks to the power of positive, authentic leadership — something I really try to bring into my work every day.

When leaders show up with honesty, vulnerability, and a genuine desire to lift others up, it builds trust and creates a sense of psychological safety. That kind of environment gives people the freedom to take risks, grow, and bring their best selves to everything we do — for our customers, our team, and ourselves.