Rachel Stewart, Head of Product on Influential Women

Influential Woman · Software, Sales Technology

Rachel Stewart

Head of Product, Listel AI

Chicagog, IL

Certifications · Degrees · Memberships

Degree Computer Science degree from DePauw University Degree Post-baccalaureate program in Math and Finance from Northwestern University Cert Real Estate License Member Chief (women's executive networking group) Member National Association of Realtors (NAR)

Her Story

About Rachel

I co-founded Listel at the beginning of 2025 with one other co-founder. We're a software company focused on sales and conversational intelligence for field sales teams. The idea came from my experience as head of product at Camping World, where I got really into building technology for sales leaders and field sales individuals. I managed all the customer-facing technology for RV sales, the Good Sam side of the business with campgrounds and partnerships, and the used RV marketplace. That's where I saw the gap - everyone's building meeting assistants for Zoom and Teams calls, but there are so many industries focused on building relationships away from a computer. We've developed a wearable that sales individuals wear when they're going out and talking to customers face-to-face, giving them the same benefits as those note-takers and pushing information to their CRMs so they don't have to run back to their car and scribble down what happened. Before Camping World, I spent 7 or 8 years in consulting doing software and data work. Right now, it's just my co-founder and I running really lean with AI tools, which means I wear a ton of hats. I do most of the customer calls, whether sales or customer success, run all our marketing, and help with testing and design while my co-founder handles the development side since he's more technical. We've already secured our first enterprise customers and raised money from a VC, though I'm not focused on raising VC money again right now.

Her Interview

Ten minutes with Rachel

01What are the biggest challenges or opportunities in your field right now?

I think definitely navigating the market as expectations of software is evolving so quickly with the influx of AI and all those great tools. I'm very pro new businesses and other startups and building with AI, I just think perception is changing so fast that it's hard, as a new company, to make a name for yourself. That's challenging. And then the typical startup challenges of how to scale and when to scale. We're not taking funding at this point in time, so our calculations of how we grow are different. I've done the VC thing before and I'm just not interested in that model right now. So I think scaling in general is always hard, but making the decisions around how to do that as we enter a new era of development is probably really hard. Hiring is always part of that - when to hire and who to hire. When you have your own company, it's very different than when you're working as head of product at Camping World where I could just say we need a new product manager and have 50 resumes on my desk by the next week. Now, as your own company, not only do you have to go source that or find someone to help you do the recruiting, you also have more weight on the decision of who to hire and what skill set you're looking for. There's a lot more pressure on the human capital side of it as a startup. If you hire the wrong person at the wrong time, you might not have the time or the capital to adjust it when you need to.

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