Molly Simas, Director of Customer Service at Portland Leather Goods, joins this session to talk about what it really means to scale with intention. Starting as a production sewer and growing into a CX leader, Molly shares her journey through rapid growth, team restructuring, and evolving leadership. She brings a grounded, people-first perspective to building strong teams while navigating constant change.

This interview has been edited for clarity.

 

Gabe Larsen: I am thinking big picture here: the idea of scaling with intention. The world is changing, and you have had your own leadership journey. How has that idea evolved for you recently?

Molly Simas: For me, scaling with intention right now means, counterintuitively, slowing down and taking a closer look at everything we have already built.

We have been operating in a system for a long time where, even though we have added leadership structure, our managers and leads are still doing a little of everything—answering emails, creating resources, handling whatever arises. We have been good at responding to needs in the moment, but not as strong at maintenance and reflection.

Now, as we scale more dramatically and hire more rapidly, we are stepping back to assess the full structure: what we already have, what is missing, and what might be duplicated. We are focused on making sure the foundation is solid before we try to build something new for the fifth time.

Gabe: That is great. There is a saying about working in the system versus working on the system—and that is such a tough balance to strike. One thing I thought was so interesting from our earlier conversation was your take on balancing heart and structure. Technology is critical to scale, but there is such a human element in customer service. How do you navigate that?

Molly: This is an interesting question because I think it often assumes leaders already have structure and need to add more heart. For me, it has been the opposite. I lead with heart—and I have had to learn how to bring in more structure.

When I started as a manager, we were a small team working in person, Monday through Friday. I had no idea how to be a manager, but I knew how to be a good person. I always emphasized, "You're a person first." I never wanted anyone to be afraid to ask for time off or admit they were having a hard day.

But I learned that endless empathy can be a double-edged sword. In a department survey I ran, someone wrote, "Empathy is your greatest strength—and also your Achilles heel." That really stuck with me.

You can empathize deeply with one person, but that can unintentionally affect the rest of the team—others picking up slack, for example, or absorbing negative energy. I have learned to hold space for people while also recognizing that we all are working together. We are a community, and we each bring things with us to work, whether we vocalize them or not.

Gabe: Such an important reflection. Your greatest strength can also be your greatest challenge. Finding that balance is key if you want to scale in a way that is both human and efficient.

You mentioned technology—how have you tried to bring tech into that idea of scale without making it feel overwhelming to the team?

Molly: This is fresh for me—we recently switched CRMs and started using Kustomer. That transition was a real learning experience.

If you are going to introduce a new tool, be really clear with your team about how it changes their current processes. Do not leave them guessing. They are trying to do their jobs while navigating change—clarity is a huge gift.

At the same time, find ways to show the tool’s value. For us, a big win was integrating quality control reporting directly into the CRM. Before, we had a spreadsheet. It was time-consuming, so people often skipped it. Now, the process is seamless. That one improvement got overwhelmingly positive feedback from the team and made them more open to the new system. When people see real improvements, they get curious about what else the tool can do.

Gabe: I love that example. So many people tuning in are trying to figure out how to realign their team’s priorities while still delivering on daily KPIs. Any advice for them?

Molly: Yes! I just came back from the Support Driven conference in Austin—it was amazing, but also a firehose of information. I left thinking, “This is all so valuable... and I need to do it all immediately.”

If you are feeling that, try identifying the top three priorities—what is most urgent? What will scaffold other efforts? For me, it was response time and training. We needed to hire and improve efficiency, and then look at the tools we already had before building anything new.

It is like a hierarchy of needs. You cannot build a voice of customer program if your basics are not in place. Take deep breaths. Accept that it takes time. Communicate with your team and your leadership about what you are focused on and why. Telling that story helps relieve pressure.

Gabe: That is such great advice. People do not always see both the day-to-day and the bigger picture, so that communication really matters.

You seem like someone who is always learning. Aside from the Support Driven conference, how else do you keep growing?

Molly: That is a great question. You often do not get all the training or support you want—so you have to build your own.

Support Driven has been huge for me. For those who cannot travel, they have a Slack community that has been incredibly helpful. Before that, I felt like I was in a silo—just figuring things out alone. In Slack, people are constantly sharing ideas and asking questions. Even if you are just searching threads instead of posting, it makes a big difference. You realize you are not alone.

Gabe: That is such a powerful note to end on. One of the reasons we are hosting this virtual event is because so many leaders have told us they feel isolated. The world is changing fast, and no one has all the answers. But there are people who are on the same journey.

Whether it is Slack communities, LinkedIn, or colleagues a few steps ahead or behind—you do not have to do this alone. That is the message.

Any final thoughts to leave us with?

Molly: Yes. I think in this moment—especially with all the AI talk—it is easy to feel overwhelmed or like everything is starting to sound the same. Give yourself time and space to reflect. Review your notes. Highlight what matters. You will gain clarity when you get specific about your situation—your life, your team, your challenges. That specificity will help you feel grounded and guide you forward more effectively than generic advice ever could.

 

Closing thoughts

Molly Simas’ journey from sewing bags to leading a growing CX team at Portland Leather Goods is a powerful reminder that scaling with intention requires both structure and heart. Her thoughtful approach to leadership and team development offers valuable lessons for any CX leader navigating change.

Remember: Your greatest strengths can also be growth areas—balance empathy with accountability. You can pull this off by prioritizing foundational needs before tackling big initiatives, and communicating your plan clearly to reduce pressure.

Want to learn more about scaling a customer experience team? Check out our interview with Jose Herrera, CEO of Horatio. 

Looking for a comprehensive tool that can help you make big strides in your customer experience? Check out Kustomer. Our all-in-one customer service platform and CRM, powered by AI, allows brands to streamline costs and operations. Explore Kustomer today!