Anna Rodriguez on redefining customer experience with AI-powered heyLibby

MVL's Jimmy Bales sat down with Anna Rodriguez, co-founder of heyLibby, to discuss her journey into tech, the inspiration behind building an AI-powered receptionist, and how heyLibby is transforming customer interactions.

Jimmy:  Your journey into tech sounds fascinating—what brought you here, and what inspired you to co-found heyLibby?

‍Anna: After graduating, I fell into tech unexpectedly, starting in a role that combined financial analysis with system administration, which gave me a strong foundation in problem-solving across disciplines. Moving to Seattle was a turning point, where I expanded into CRM, marketing automation, and product engineering, and my time at Zillow gave me invaluable insights into scaling businesses and building products with customer feedback at the core. 

Over the years, I've had countless ideas about what to build and how to solve inefficiencies, so when I got the call to co-found a company, I was all in. With Spencer and Tony in the mix, it felt like a dream team—I couldn't say no. 

‍Jimmy: With such a wide range of experiences, were there specific moments or challenges in your career that made you think, 'I need to start my own company'?

Anna: I've always thrived in roles that require juggling multiple priorities, which prepared me for the fast-paced nature of running a startup. Before founding heyLibby, I worked at Avalara as Director of Enterprise Architecture, where I led a major initiative to improve "speed to lead," ensuring sales reps could respond to inbound leads within minutes.

The complexity of that project—managing systems, coordinating across teams, and striving for faster responses—made me realize how transformative AI could be in solving these challenges. When Tony approached me with the idea of an AI SDR, it aligned perfectly with the inefficiencies I'd been working to address. It was an easy decision to take this risk of building a startup, and create a solution I knew businesses needed.

Jimmy: heyLibby sounds like a game-changer—how does it work, and what makes it so different from traditional reception methods?

Anna: heyLibby is an AI-powered receptionist designed to handle customer interactions across email, text, phone, and chat—24/7. At its core, heyLibby uses tools like text-to-speech and speech-to-text, but what sets it apart is its advanced conversational analysis. For instance, speech models have improved significantly since early 2023—what used to sound robotic is now nearly indistinguishable from a human voice. Leveraging these advancements, heyLibby analyzes conversations in real-time, incorporating elements like sentiment analysis to drive intelligent, context-aware responses.

One major advantage of AI in this context is its consistency and accuracy. In my previous roles at companies like Zillow and Avalara, we faced the challenge of training hundreds of salespeople to deliver consistent, correct messaging—a near-impossible task. heyLibby solves this by providing accurate, brand-aligned responses every time, all while adapting to the customer's tone and language to ensure a personalized experience.

Our ideal customer profile (ICP) includes recreation and wellness companies, such as gyms, dance studios, massage centers, and other subscription-based businesses with physical locations. These industries often deal with demanding customers and significant churn—50% of members cancel within six months. heyLibby addresses this by using AI to always provide a superior customer experience, ensuring that all inquiries are answered immediately.  As for the near future of heyLibby, we plan to use AI to deeply understand customer preferences and behaviors and act on them for our customers.  This personalized approach will help businesses keep their customers engaged and happy.

If someone skips their usual winter spray tan, heyLibby might send a deal in December to re-engage them. By answering questions instantly and providing proactive, data-driven outreach, heyLibby reduces churn and improves customer satisfaction—ultimately driving better outcomes for both customers and businesses.

What sets heyLibby apart is its ability to seamlessly handle all four primary communication channels—email, text, chat, and phone calls—from day one. Many competitors start with just one channel and require businesses to adopt multiple tools over time, but we knew small and medium-sized businesses needed an all-in-one solution. With heyLibby, you train it once, and it delivers consistent, context-aware responses across every channel without the need for technical expertise.

The platform is designed to be simple and intuitive, so businesses can get started in minutes and focus on what matters—serving their customers—not managing complex software. By combining ease of use with powerful conversational AI, heyLibby saves time, reduces friction, and provides a better overall experience for businesses and their customers alike.

Jimmy: User feedback can shape a product in surprising ways—what have you learned from heyLibby's users, and how is it influencing your roadmap?

Anna: User feedback is at the heart of heyLibby's development. One common request from our fitness and wellness clients has been for appointment scheduling via phone, and we're actively building that feature to expand what heyLibby can automate. For rare cases like lost-and-found inquiries, heyLibby seamlessly notifies admins with a transcript for manual follow-up.

By focusing on accuracy, adaptability, and continuous improvement, we ensure that heyLibby evolves to meet our customers' real-world needs while consistently delivering an excellent experience.

Jimmy: Being a first-time founder comes with a learning curve—what challenges surprised you the most, and how did you work through them?

Anna: One of the biggest challenges I faced was self-doubt. As a founder, especially in the early days, you need to project confidence to fundraise and lead, but imposter syndrome was real behind the scenes. It's something my co-founder and I have talked about openly, and I know it's not just me—it affects everyone, regardless of gender or experience.

Early on, I often hesitated to share ideas, worried they weren't good enough. Over time, I realized my contributions were just as valuable—sometimes even better. Gaining confidence has been transformative, and I now embrace my role as co-founder and CTO with pride.

Jimmy: For founders just starting out, what advice would you share to help them navigate the ups and downs of entrepreneurship?

Anna: First, trust that you're here for a reason. If someone has invested in you, it's because they see your potential—you didn't trick anyone. Second, as cliché as it sounds, fake it until you make it. Confidence comes with experience. I doubted myself for years, but diving into the work made me realize I had become the expert I once thought I wasn't.

Lastly, prepare for the rollercoaster. Entrepreneurship is full of highs and lows—sometimes in the same day. Expecting twists and turns makes navigating and staying grounded through it all much more accessible.

Jimmy: How has working with MVL supported your journey, and what advice would you give to a founder considering working with us?

Anna: MVL has been incredibly helpful, especially with its expertise and network. The people are smart, supportive, and approachable, which is a huge comfort during the stressful moments of startup life. We've made valuable connections through MVL, from third-party firms for outsourced development and UI/UX to other founders.

For founders considering joining, I'd say absolutely do it—and take full advantage of the opportunities to connect. If you're invited to events or have a chance to visit the office, go. Talking to other founders and engaging with the community can make a big difference. Those interactions are invaluable for building relationships and getting support.

Jimmy: How can businesses start using heyLibby today?

Anna: If you're curious about how heyLibby can help your business, we'd be happy to chat! Reach out to us directly or visit our website to learn more.

Founder Spotlight is a series dedicated to bringing you insights into the founder journey, lessons learned from startup leaders, and a behind-the-scenes look at some of the most compelling tech companies in our community.