Welcome back to another installment of Cresta Crew, where we get to shine a spotlight on Cresta team members from around the organization. In this series, we get a peek into who these individual Crestans are, how they got here, what their day-to-day looks like, and why they’re excited about Cresta’s future.
Today, we’re chatting with Stacy Osorio, Director of Customer Success.
Tell us about yourself – what is your background?
Growing up, I was always drawn to technology. I looked forward to my computer classes and knew early on that I wanted to build a career in the tech industry. I pursued a degree in IT and Business Management, and after graduating, I landed my first role at a Boston-based startup called Localytics, an analytics and marketing platform. That was the beginning of my start-up career.
I began my career as a Sales Engineer. Over time, I gravitated toward roles that allowed me to work more closely with customers, supporting proofs of concept, campaign launches, and guiding them to that “ah-ha” moment. That’s what ultimately led me to post-sales and Customer Success.
Since then, I’ve worked at several high-growth startups like Branch. I started as a Technical Account Manager and eventually led the Enterprise Customer Success team, driving strategy and expansion across the Americas. Most recently, at Pendo, I led an Enterprise Customer Success team and a Customer Growth team focused on scaled success strategies.
My adaptability and love for working with people and solving problems have stayed consistent throughout my career. I’m passionate about helping customers reach their goals while ensuring my teams are supported, growing, and learning alongside them. It’s about creating a meaningful impact for our customers and for the people behind the product.
What inspired you to join Cresta?
I have been following Cresta for a few years now. I was drawn in by the company’s exciting stage and the product itself. It felt like the right time to return to a smaller, fast-paced startup environment. Most of my background has been in MarTech and Analytics, so the opportunity to work in the AI space and contribute to a company leading the industry piqued my interest.
What stood out to me about Cresta was its approach to AI. Unlike many companies where AI is an add-on, here at Cresta, AI is at the core of what we do. It’s not just a feature, it’s foundational. That level of focus and innovation was incredibly compelling, and paired with the impressive list of Cresta customers, it felt like an opportunity I couldn’t pass up.
What is your role at Cresta?
I’m a Director of Customer Success, focusing on enabling and empowering our Customer Success Managers (CSMs) to be strategic advisors to their customers. As a Success team, we aim to guide customers through their transformational journey. Ultimately, we strive to drive retention and growth for our organization while also being a key partner in innovation and progress within the contact center space.
As a leader, I stay connected to my CSMs and their day-to-day customer interactions, identifying both strengths and areas of opportunity to strengthen our customer relationships. While I’m still relatively new to Cresta, I aim to use all of those insights to help shape strategies that better support our team so they can deliver even greater value to their customers.
How did you get into this line of work?
My peers drove my introduction to leadership. I’ve always had a habit of documenting and sharing my learnings (I still do), whether it was a challenge I faced, how I approached solving it, or where I needed support. That transparency helped create awareness across the team that we are all in this together, and over time, I became a go-to resource.
As I continued supporting and mentoring peers, it became clear that I enjoyed coaching just as much as being a CSM. That led to a formal team lead role where I helped onboard new hires, supported peers, and contributed to team development. This then paved my way into leadership.
What does a typical day look like?
As you will likely hear from anyone else in a customer-facing role, every day is different. I start each day by reviewing emails and my to-do list to understand my priorities clearly. This helps me carve out focus time and stay aligned on what I need to accomplish.
My days usually involve a mix of customer-facing meetings, where I stay close to the work my team is doing, and internal leadership meetings focused on strategy and cross-functional alignment to support our customers and each other. I also aim to ensure that if my team needs help, I’m an available resource they can rely on. Whether that means getting in the weeds alongside them or helping push things forward at a higher level. Like many of us in leadership, I strive to balance tactical support and strategic guidance to help our teams and customers succeed.
What about the product gets you excited?
If you’re a former co-worker reading this, brace yourself because it’s not the data or, as we call it here at Cresta, “Insights.”
Instead, it’s our AI Agent. Seeing the demos we’ve created for customers has been incredible. I was blown away the first time I saw one during an all-hands. I already knew the product was impressive, but I hadn’t fully realized the level of innovation happening behind the scenes to deliver such a thoughtful virtual experience. Not to mention, one capable of handling complex issues with patience and empathy!
What do you think is the most important skill for a new Crestan to have?
Natural curiosity is one of the most important qualities any new Crestan can bring. You need to be genuinely interested in understanding the why behind things and then taking it further to build a deeper understanding. This will be fundamental in helping you make an impact on your career.
What are some of your earliest learnings from working with our customers?
Our customers aren’t just looking for a tool; they’re looking for a strategic partner. They want us to be thought leaders who can guide them, offer strategic insights, and bring creative ideas to help their agents succeed and drive business outcomes.
They chose Cresta because they’re looking for someone to tell them what the product can do and how to use it to differentiate themselves and meet their goals. When customers are fully enabled and adopting the platform, they’re excited about the impact and value of the partnerships they’ve established with their account team. It’s been fun to join customer calls and hear our customers sing the praises of their CSMs!
What do you love to do with your time when you’re not at work?
Outside work, I love exploring new restaurants and wineries with my husband and our puppy, Paddington. We live in wine country, so we’re always discovering new places nearby to try out.
When we’re not exploring the local area or hanging with our pets, my husband and I love to travel. One of my favorite places to visit is Peru, but I may be biased because I have family there and always get a home-cooked meal!
