Kailee Heffler Of SmartBear On 5 Things We Can Each Do To Make Social Media And The Internet A Kinder And More Tolerant Place
…Positive comments: Social media often seems like a place people go to criticize, but why not leave a positive comment! Small acts of kindness can brighten someone’s whole day. Imagine if everyone committed to spreading positivity, social media would be a much friendlier place…
As a part of our interview series about the things we can each do to make social media and the internet a kinder and more tolerant place, I had the pleasure to interview Kailee Heffler.
Kailee Heffler is Senior Brand Activation Specialist at SmartBear, where she brings brand stories to life through integrated campaigns, executive thought leadership, social media, and cross-channel content strategy. Since joining SmartBear, Kailee has advanced from Brand Communications Specialist to a senior role, where she drives brand consistency and visibility across internal and external touchpoints. Her background in employer branding and social media at EverQuote laid a strong foundation for creating compelling narratives that engage both customers and employees. Kailee also brings early experience in broadcast journalism, including news production and on-air reporting, which sharpens her eye for timely, authentic storytelling. She holds a bachelor’s degree in journalism as well as a master’s degree in interactive media and communications from Quinnipiac University, where she served as a digital coordinator for Quinnipiac and executive producer at Q30 Television.
Thank you so much for doing this with us! Our readers would love to “get to know you” a bit better. Can you share your “backstory” with us?
Definitely! I originally went to college with the goal of becoming a news reporter — but life had other plans for me. While in school, I had the opportunity to run social media for my university and quickly realized how much I loved telling stories in a way that could reach and connect with people, without being in front of a camera. My boss there was incredibly encouraging and helped spark my passion for social media as a powerful tool to build community, share meaningful stories, and engage with individuals in an authentic way. After graduating, I knew I wanted to pursue a role that allowed me to do just that.
Since then, I’ve focused my career on developing social strategies that foster connection and engagement. At SmartBear, I’ve had the opportunity to take that even further by shaping and growing our social channels in exciting and impactful ways.
Can you share the most interesting story that happened to you since you started your career?
I would say the most interesting story since I started my career began right at the start, launching my career during a global pandemic. I graduated with my bachelor’s and master’s degrees in May 2021 and started my full-time job that June. Like many, I never expected to begin my first full-time job entirely online.
Starting my career remotely came with its own set of challenges. I had to adapt to a company culture that was adapting into a “new normal” and build relationships with coworkers, all without ever stepping into an office. It was a crash course in flexibility, communication, and self-motivation, but one that taught me valuable skills I still carry today. I am lucky to have had such great coworkers at my first job who also helped ease my transition.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
One of the funniest mistakes I made was when I was new to SmartBear. I was getting my bearings and learning everyone’s names as one does when starting a new job. One first name I did recognize was our CEO’s. So, when I received a ticket to publish an article on our social channels written by someone with the same first name, I thought, “Cool! The CEO submits tickets.”
Spoiler alert: He doesn’t.
I went ahead, wrote the caption, tagged the CEO, and published the post. Within minutes, the Slack messages started rolling in — turns out I had tagged the wrong person. The article had been written by an employee (who I had not met yet), not the CEO.
It was embarrassing, but it taught me a valuable lesson: slow down and double-check everything, especially names, before hitting publish.
Are you working on any exciting new projects now? How do you think that will help people?
Yes! I’m about to kick off a project I’m calling “Sophisticatedly Unhinged Social.” I’ve noticed a lot of brands are shifting away from being overly polished and “perfect” and instead leaning into humor, memes, and self-awareness. It’s a refreshing change and one that I believe has a lot of potential.
The idea behind this project is to strike the right balance; we’re still a professional business, so we don’t want to go completely off the rails, but I believe there’s an opportunity to be strategically bold and human in how we show up online.
I’m excited to get to work on this because I think it is an approach that can help reshape how consumers view corporate companies. When a brand shows some personality, shares its values, and isn’t afraid to have a little fun, it builds trust. People connect with authenticity, and that connection benefits both the company and the consumer.
Ok, thank you for that. Let’s now jump to the main focus of our interview. Have you ever been publicly shamed or embarrassed on social media? Can you share with our readers what that experience felt like?
Yes, I have been. I believe this can happen to anyone, whether you have 20 followers or 2 million. My experience was I accidentally spelled “Amalfi” wrong when I made an Instagram story highlighting my trip there. In my head, I was saying it as “Al-malfi.” Now, this should be no big deal, especially since it was my personal account, but I couldn’t believe how many people felt the need to correct me, some people I had barely interacted with before on social. On one hand, I appreciated the heads up, but on the other hand, it is my personal account, so no harm, no foul.
It was embarrassing, and honestly, a bit discouraging to see so many people have a negative reaction to my mistake.
What did you do to shake off that negative feeling?
I told myself mistakes happen because they do! I also told myself to forget about it because I wasn’t going to let one mistake on my personal account ruin my trip to Italy!
Have you ever posted a comment on social media that you regretted because you felt it was too harsh or mean?
Never. As someone who works in social media, I recognize there is a person behind every post, whether that is an influencer’s own account or a corporate account, and that person has feelings. I’ve always tried to approach comments with empathy, even when I disagree. Being intentional with my words is part of how I show respect for others online.
Can you describe the evolution of your decisions? Why did you initially write the comment, and why did you eventually regret it?
While I haven’t posted anything I’d describe as mean or harsh, hypothetically, if I were to write a comment that was critical or emotionally charged, I imagine I’d want to take a moment before hitting “send.” In that situation, I might initially write something in the heat of the moment — perhaps intending to be direct or candid — but then choose to step away and revisit it later with a fresh perspective.
That pause would give me a chance to evaluate whether the tone truly matched my intent. I could see myself softening the wording or reframing the feedback, making sure I am mindful about how the comment may come across. Pausing before posting is just as important as pausing in a difficult conversation in real life. It gives you space to check your tone and ask: Is this helpful? Is this how I’d speak to someone face to face?
When one reads the comments on Youtube or Instagram, or the trending topics on Twitter, a great percentage of them are critical, harsh, and hurtful. The people writing the comments may feel like they are simply tapping buttons on a keyboard, but to the one on the receiving end of the comment, it is very different. This may be intuitive, but I feel that it will be instructive to spell it out. Can you help illustrate to our readers what the recipient of a public online critique might be feeling?
For the person writing the comment, it’s often just a fleeting moment. They’ll type it out, hit publish, and move on — likely forgetting about it within a day or two.
But for the person on the receiving end, it can be a very different experience. It could cause them to feel hurt, ashamed, anxious, or even vulnerable, especially when it is a public forum for all eyes to see. And those emotions don’t simply fade.
Imagine spending time creating content you are proud of and instantly having it torn apart by strangers. This type of experience can shake someone’s confidence and cause them to want to stop posting overall.
I’ve seen plenty of influencers, creators, and even celebrities open up about how much those harsh, critical comments affect them. No matter how many followers someone has or how successful they may seem, every person behind the screen is still human.
Do you think a verbal online attack feels worse or less than a verbal argument in “real life?” How are the two different?
Worse, for sure. An online attack often feels more painful because it’s coming from a complete stranger, someone who knows nothing about you but feels the need to judge or insult you. There’s a cold detachment to it, which feels harsher to me.
In a real-life verbal argument, there’s usually more context — emotions, history, or even the chance for dialogue. But online, it is as simple as someone deciding they didn’t like what you posted and making sure you feel that.
What long term effects can happen to someone who was shamed online?
Being shamed online can have lasting psychological effects. Even if someone appears unaffected on the surface, most people — whether they would admit it or not — struggle when feeling rejected, disliked, or humiliated. That kind of exposure leads to anxiety, low self-esteem, depression, or a lingering fear of what might happen if they express themselves again.
Over time, it might affect a person’s confidence and sense of safety, especially if the shaming was public. For some, the emotional toll lasts longer and can alter how they navigate online spaces in the future.
Many people who troll others online, or who leave harsh comments, can likely be kind and sweet people in “real life”. These people would likely never publicly shout at someone in a room filled with 100 people. Yet, on social media, when you embarrass someone, you are doing it in front of thousands or even millions of people, and it is out there forever. Can you give 3 or 4 reasons why social media tends to bring out the worst in people; why people are meaner online than they are in person?
- We Hide Behind Screens: People feel protected behind their screens, so they feel empowered to say things they’d never say face-to-face (most of the time). It feels less personal, even when it’s not.
- People become Profiles: On social media, it is easy to reduce someone to a username, nothing more. Empathy tends to get lost in the scroll.
- No Immediate Consequence: In person, you’d see someone’s reaction to your comment — a flinch, tears, or silence. Online, that emotional feedback is gone.
- We Project Our Pain: Sometimes people lash out online because they’re stressed, frustrated, or jealous. The internet has become a place to vent those emotions, often directed at strangers.
If you had the power to influence thousands of people about how to best comment and interact online, what would you suggest to them? What are your “5 things we should each do to help make social media and the internet a kinder and more tolerant place”? Can you give a story or an example for each?
- Pause before posting: Before jumping into an argument online, stop and ask yourself: Is this really worth my time and anger? Often, online flights don’t lead anywhere positive, so take a moment to decide if your comment will help or hurt. Sometimes, the best response is no response at all.
- Empathize: We often forget that behind the username is a real person with feelings, challenges, and a life we don’t see. A little empathy can turn a potential conflict into a moment of support.
- Take a break: Social media can be overwhelming. So, unfollow or mute accounts that drain your energy. Taking breaks helps protect your mental health and gives you space to return with a better mindset.
- Practice active listening: Instead of reacting with judgment, try to understand the other person’s POV. If something isn’t clear, ask a question instead of leaving a harsh comment. This approach opens the door to respectful dialogue.
- Positive comments: Social media often seems like a place people go to criticize, but why not leave a positive comment! Small acts of kindness can brighten someone’s whole day. Imagine if everyone committed to spreading positivity, social media would be a much friendlier place.
Freedom of speech prohibits censorship in the public square. Do you think that applies to social media? Do American citizens have a right to say whatever they want within the confines of a social media platform owned by a private enterprise?
Yes, I believe we do. Social media has become the modern public square, where people debate, organize, and express themselves. Even though platforms are privately owned, they have enormous influence over public discourse. If we don’t protect speech in these spaces, we risk allowing a few corporations to decide what’s acceptable to say. That’s not real freedom. Private ownership shouldn’t erase the public’s right to speak openly. I believe a lot of the social media platforms would lose users if they censored what we could say.
If you had full control over Facebook or Twitter, which specific changes would you make to limit harmful or hurtful attacks?
If I had full control over Facebook or X/Twitter, I would add a feature that detects harmful or aggressive language before a post is published. When certain flagged words or phrases are used, a pop-up would appear asking the person if they’re sure they want to continue with the post.
It wouldn’t block or censor their speech, but it would create a moment of pause. Sometimes, that brief second of reflection is all it takes to reconsider posting something hurtful.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“Everything happens for a reason.”
This is a life lesson my mom instilled in my sisters and me from a very young age and it is something I wholeheartedly believe in. That mindset has guided me through both personal and professional moments of uncertainty or disappointment, and it has never failed me.
One example that stands out is from earlier in my career when I had my heart set on a specific job at a particular company. I went through multiple interviews, heard positive feedback, and truly thought it was a perfect fit — until they ghosted me. At the time, it was incredibly discouraging, and I ended up accepting a different offer.
After starting my new role, the recruiter who had ghosted me reached back out, letting me know there had been layoffs and the hiring manager’s role was eliminated. It was at that moment that I realized everything happened for a reason, and I was right where I needed to be.
We are blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂
I would love to have a private lunch (or perhaps tea!) with Kate Middleton! She has become one of the most poised, influential women in the world, yet she maintains a strong sense of self and purpose under public scrutiny. I admire how she has used her platform to champion causes like mental health, early childhood development, and family well-being. She seems like a genuinely kind person who probably has some great stories to tell!
She also seems to balance modern expectations with centuries old tradition seamlessly, and I would love to ask her how she navigates the pressure of being in the public eye, her vision for the next generation of royals, and what she loves the most about her family. Plus, I think it would be fascinating to get a behind-the-scenes perspective on life inside one of the most watched families in the world.
How can our readers follow you on social media?
https://www.linkedin.com/in/kailee-heffler/
Thank you so much for these insights! This was so inspiring!
Kailee Heffler Of SmartBear On 5 Things We Can Each Do To Make Social Media And The Internet A… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.