After Helping Her Family Connect During Covid, This Founder’s Chatbot Now Brings Remote Teams Together

Think back to the early days of the pandemic: How did you react when you heard about mandatory lockdowns? Many introverts had no problem adjusting to the new normal, but extroverts had a particularly hard time. As the world continued to pause, families weren’t allowed to see one another and in-person gatherings were forbidden. No one knew when things would return to normal, if at all. Kaylee McHugh, the founder of ChattyKathi, watched her outgoing, basketball-loving husband struggle at home, but she knew she could help. 

The idea started simple. Kaylee created a chatbot to help her mother and husband talk about basketball because they both loved the NBA. The chatbot sent them conversation starters via SMS to encourage conversation. It worked: “They text one another about more things than basketball. They were bonding, which was a wonderful thing for me to see. We lived across the country so rarely managed to meet in person and never during Covid.”

In early 2020, business owners sent their staff home, worrying how remote working would impact team bonds that had taken years to build. Executives struggled with employee motivation and camaraderie was at an all-time low. Kaylee wondered: Could ChattyKathi bring people together in this time of uncertainty? 

If at First You Don’t Succeed…

At the start of the pandemic, Kaylee was regrouping after a failed startup. She was a software engineer with a steady paycheck and had resigned to launch her first business. When that failed, she and her cofounder parted ways. Kaylee’s coping strategy? “I watched Outlander in bed for two weeks straight.” Understandably, Kaylee was wary about trying again, but the chatbot beckoned.

Should she play it safe and apply for a job? She scoured job boards but found nothing that interested her. “None of them felt like a good fit. They didn’t feel like something I wanted to do anymore. I had unlocked a whole new set of skills at my first startup. I could pay a hundred thousand dollars for an MBA or keep building, continue my education with a second startup.”

As the idea percolated in Kaylee’s brain, she reached out to a friend, Ericka Schubert, who was equally intrigued. They decided to join forces and create a company that helps managers lead teams more effectively using conversation starters. They envisioned employee profiles that included more than just your average profile picture – as if Tinder and Slack had had a baby. The goal was to make the workplace more personable, authentic, and fun.

Erica comes from the film festival world. For a decade, her job was to tell stories through film. Kaylee was a literature major before she was a software engineer. She’s equally passionate about storytelling. The plan was to use technology to help employees share their stories with teammates, and in turn, build relationships that united the company despite the distance.

The company name reflects the founders’ ethos. As Kaylee explains: “‘Chatty Kathy’ is a term used to describe someone, often a woman, who talks a lot. For a long time, it was a bad thing to be called a Chatty Kathy. It meant that you were asking too many questions, being too nosy, or being annoying. But in reality, Chatty Kathys were just trying to be nice by getting to know the people around them. 

“As a female-founded company, we’re reclaiming the term ChattyKathi. While women may have been called ‘Chatty Kathys’ negatively in the past, we want everyone to proudly and confidently be able to ask questions, engage in interesting conversations, and share about themselves.”

The founders built a prototype. Kaylee designed the interface and customer experience. Then they asked friends and colleagues for feedback. “Many founders mistakenly believe you’ll attract thousands of customers overnight. But pretty much everything in the startup world is a soft launch. Just like ours. So we got things done incrementally and tried things out and experimented and continued to fine-tune. We slowly got the word out.”

Beta Testing Amid Lockdowns

Covid wreaked havoc on the traditional office as we know it. Lots of companies jumped in to fill the interpersonal void. Team building exercises in the form of Family Feud-type games and Zoom cocktail parties became part of our nomenclature. But ChattyKathi wanted the engagement to last longer than a forty-five-minute session. The founders wanted to help managers get to know their employees better, not just during the onboarding process.

Kaylee explains, “Many companies struggle to motivate and engage remote employees because it’s incredibly hard to get to know people. Some find the answer to that in surveys and performance reviews. But our research shows that the best way to engage a team is to get to know one another and make sure that everyone feels like they belong.”

Kaylee and Ericka were lucky to have friends willing to beta-test the product at their respective companies. The honest feedback allowed the founders to tweak and adjust mid-development. They also researched remote-work environments by reaching out to team managers, c-suite executives, remote students, and more. They asked questions, conducted surveys, and listened to employee experiences. The idea was to make the product work for every type of user.

“Every team member gets a profile so employees can see one another outside of work,” Erica says. “Whether it’s pictures of pets, family, and more. You’re more than just a face on a screen. Then we help team managers send out different conversation starters. So, we may see that one team loves hiking, dogs, and anime. We will send out conversation starters about those things.”

Pricing scales with customers’ needs. ChattyKathi offers a free trial for prospective customers to try out the service, no coding or credit cards required. If someone wants to go further, they buy the plan that matches the number of employees and teams under their purview. Plans start at $99 per month.

Growing an Internal Team That Isn’t All About Work

As ChattyKathi grew, the founders hired two part-time employees. The work-life balance was important to them, so they worked hard to create an environment that encouraged a life outside of work. 

“During Covid, a lot of women had to juggle childcare and full-time work,” Kaylee says. “Many asked employees for part-time positions but were turned down. We purposefully created part-time positions because, as a tech company with two female founders, we didn’t want women to lose out on opportunities because of their added responsibilities.”

In a sense, it was exactly the environment that they were creating for their customers. By helping companies bond, productivity would naturally skyrocket: “In work, sometimes we get so focused on output and see that as the only thing that matters. We begin to reduce ourselves down to one-dimensional people. Work isn’t everything.”

Much like the early days, ChattyKathi continues to iterate with feedback. It has spent the last few months interviewing team managers in remote positions to understand what else it needs to be successful. The results? Managers want more guidance on how to have tough conversations with their teams. “Managers want to build resilience, confidence, and trust in their teams. They might be exceptional leaders, but now they have to manage the psychological impact of remote working and that’s an entirely different animal.”

Currently, ChattyKathi has a database of over 1,400 conversation starters and 140 different interest libraries ranging from hiking to gardening and everything in between. None of the questions are location-specific, either: “Each of us in the world is very limited to our worldview. We asked an international audience (personal friends and Redditors) to read our content and give us their opinions. Every culture is so unique and each perspective is insightful.”

Patient Persistence

To spread the word, ChattyKathi uses a combination of SEO, Facebook ads, LinkedIn, and an email marketing company, They find the most success with email outreach. Prospective clients don’t have to do any work, and ChattyKathi meets them directly in their inboxes. Kaylee admits that she was initially skeptical of this approach. “I’ve talked to a lot of mentors about it. They all assured me that this is what B2B SaaS companies do. I haven’t looked back.”

And when someone rejects Kaylee’s pitch? That’s okay, too. “I learn a lot when people say yes, but I learn even more when they say no. It teaches me that we’re not hitting the mark and changes our approach.”

Kaylee is glad she rejected the “safe” corporate job. “The journey is scary for everyone,” Kaylee says. “Even the most seasoned entrepreneur is scared to take that dive. And you know what? It’s going to be ten times harder than you thought it was going to be, but it will be one hundred percent worth it. You will learn so much about yourself and what you’re capable of achieving during that journey. I’ve gained confidence, skills, and incredible relationships.”

Now that the world has opened up, Kaylee’s husband and her mother can finally catch an NBA game live. 

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Andrew Gazdecki
Andrew Gazdecki
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

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