Jeremy Heilpern Of Ammunition: 5 Ways Empathy Will Affect Your Leadership

Relationships. I think first and foremost empathy leads to stronger relationships. It goes back to the notion of actually caring. Anyone can call themselves a “boss” and lead through authority. But as I told someone on the team recently, if you need authority to lead then you probably aren’t cut out to be a leader. Empathy, and good relationships, mean you’ll lead because others want to follow. The distinction between the two is very important.

Empathy, the ability to understand and share the feelings of another, is increasingly recognized as a pivotal leadership trait. In an ever-evolving business landscape, leaders who exhibit genuine empathy are better equipped to connect, inspire, and drive their teams towards success. But how exactly does empathy shape leadership dynamics? How can it be harnessed to foster stronger relationships, improved decision-making, and a more inclusive work environment? As part of this series, we had the pleasure of interviewing Jeremy Heilpern.

Jeremy Heilpern is the founder and CEO of Ammunition, a full-funnel advertising agency based in Atlanta, Georgia. Founded in 2017, Ammunition has quickly grown to become a nimble powerhouse of talent, consistently ranking among Atlanta’s top and fastest-growing privately held companies in the past three years and the fastest-growing advertising agency in 2023 by the Atlanta Business Chronicle. Ammunition also secured a spot among Atlanta’s top 25 largest advertising and marketing firms in 2023.

Jeremy’s love affair with advertising began at 14 when he founded his first digital agency. Shortly thereafter, he was studying at the Art Institute of Atlanta, earning a BFA before turning 19. After graduating, he spent time at a few Atlanta-based advertising agencies, where he grew from a director, to the C-suite and eventually president before the age of 28. At his last stop, he transformed a traditionally-focused 30-year-old agency into a robust digital agency, where under his guidance, the firm doubled in size as he built a vigorous technology development practice, re-launched its media department, and built in-house CRM and automation capabilities.

Jeremy’s impact has been felt across numerous Fortune 100 companies, startups, and emerging brands, and even a presidential campaign. He’s helped shape brands like Mitsubishi Electric, Samsung, LG, Crawford, Westlake, and many more. Above all, he’s fueled by a passion for building great brands, leading the development of great work, and building great client-centric teams.

Thank you so much for joining us in this interview series. Before we dive into our discussion about empathy, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I’m not sure where it came from exactly, but my love for advertising — and the digital space in particular — has been a constant in my life for as long as I can remember. I started my first agency in my parents’ basement at 14 years old, and I’ve yet to make a dollar doing anything else ever since.

Fast forward a few years, I was turning 19, I had just graduated with a BFA in advertising, and I started working with a few well-known agencies around Atlanta, mostly on a contract basis, as I was convinced I wouldn’t ever officially work for anyone. That didn’t quite work out as I expected, and over the next decade, I found myself climbing the ranks at other firms as I grew from a director, to the C-suite, and eventually to president of one of Atlanta’s oldest agencies, before eventually resigning to launch Ammunition in November of 2017.

I saw an opportunity to build an agency that wasn’t fighting muscle memory developed during a bygone era of advertising. I was going to build an agency whose very DNA was written for the way brands need to connect with their audiences today. After my last day at the previous shop, I signed a lease for office space in Midtown Atlanta, and I got to work building a full-service agency that did just that.

Can you share the most interesting story that happened to you since you started your career?

The most interesting? That’s a tough one. On a personal level, I’d have to say deciding to start my own business has to be at the top of the list. And doing so after ten years of success at other firms just to start back at ground zero made it all the more risky. Startups are difficult, and advertising can be difficult, so when you put those things together, it’s not easy. On top of that, I had a keen understanding that the world didn’t need another advertising agency. For us to be successful, we had to be hyper-focused on the brands we were going to serve and provide them with a level of service they couldn’t find anywhere else. That approach proved successful, and after the first couple of years, we hit our stride growing at a 50% year-over-year pace each year since.

What do you think makes your company stand out? Can you share a story?

I mentioned that we were hyper-focused on certain brands when we started. Specifically, for the first couple of years, we exclusively worked on brands in the home and building products space. This gave us a meaningful north star from a business development standpoint and allowed us to provide our clients with value as we became experts in their category while applying experience from our work on like-minded brands with our proven results. This approach garnered success, so we began to look at ways we could help brands with similar DNA and expand outside of the home and building category. This led to a focus on what we described as brands navigating long-term selling environments, often with complex paths to purchase and numerous decision-makers. That led to work in higher education, insurance, financial services, and other sectors. Our approach centers on a distinctive messaging architecture that tailors creative content based on audience segmentation, utilizing continuous engagement and automation.

Then, in the summer of this year, we decided to acquire Mad Hat Creative, Atlanta’s premier video production company, and integrate it fully into our agency offering. This helped fuel our continued growth and expansion into other verticals, bringing new clients into our full-service agency offering while cross-selling video production services to our existing clients.

What that means, and to answer the questions now more directly, is pound for pound, we offer a truly comprehensive and nearly unrivaled full-service agency experience, encompassing everything from brand strategy, positioning, and video production to technology development, and media planning and buying. With all these services under one roof at our Atlanta office, we provide clients with a genuinely holistic approach to managing their business. Our focus is on delivering recommendations that are truly aligned with our clients’ needs, rather than prioritizing what benefits our agency’s bottom line. At Ammunition, we’re dedicated to serving in whatever capacity brings the most value to our clients.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

1. ​​Persistence: Persistence in trusting our vision, trusting the process, and focusing on the mission we set out to achieve for ourselves. Times will be tough, and things won’t go as we plan, but being persistent in achieving one’s goals is mission-critical to long-term success.
2. Resilience: Overcoming challenges, like market downturns, by staying focused and optimizing operations is crucial. It’s about not giving up and finding ways to always improve even when times get tough.
3. Empathy: Valuing and supporting the team, especially during stressful projects, is vital. Understanding their needs and showing appreciation is critical to building a strong, collaborative work environment.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

For me, the most important, and subsequently difficult, decisions we make are the ones that result in the hiring or firing of another person. I believe that the most sacred part of my job is ensuring the integrity and longevity of the jobs we create. When making decisions to hire, we work to make sure that when we do, we’re creating a long-term position in the company and being mindful that we are not reacting to a moment of stress or emotion. This helps to ensure we’re using objective reasoning in making that hiring decision and thus increasing the chances that the role we create is one that will be around long-term.

On the other hand, when we are deciding to terminate someone, we do our best to ensure that if it finally gets to that point, it doesn’t come as a surprise to that person. We take seriously the role that the jobs we provide play in the personal lives of those who have them, even when we’ve concluded that someone is not the right fit for the job or the organization. I can think of times that this has happened, and we’ve held on too long hoping to make it work because we don’t want to make the hard decision. In reality, that’s only ever likely to cause more problems, and the right thing to do for all involved is to make the hard decision and move forward. When we do, we often seek to provide severance and job placement support to try and ease the transition for the individual as best we can.

At the end of the day, while we have a business to run, we also have to be mindful that a human being is always on the other side of those decisions — and we need to be as fair and as kind as we can.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. How do you define empathy in a leadership context, and why do you believe it’s a vital trait for leaders to possess in today’s work environment?

I define empathy as the ability to understand, relate to, and effectively respond to the emotions and perspectives of others — EQ vs IQ.

I think for us to be effective as leaders, we need to be in tune with the feelings and needs of those under our stewardship. Understanding what they need helps us to know how to get the best out of them. It also helps us to keep a pulse on the organization in a way that helps identify team members who may need our support when times are tough for them, whether professionally or personally, as well as to identify people or moments that could prove harmful to our culture and what it feels like to work for the company.

Effectively deploying empathy towards others is vital, as at its core, it’s really about building trust with others. We’re not always going to agree, and feelings aren’t always necessarily facts, but understanding why someone feels the way they do helps us to not only support them, but it helps us to guide them when they need to grow and push through in a certain direction.

In the role I play as CEO, I try to remind everyone that we’re all human, none of us are perfect, and every single one of us is going to mess up. That’s okay. It’s about what we do after we mess up that matters. Building that foundational layer of trust and understanding, I think, is important in creating an environment where everyone can excel, to do their best work, and to hopefully live their best lives.

Can you share a personal experience where showing empathy as a leader significantly impacted a situation or relationship in your organization?

I once hired a senior executive to lead a team that, in time, turned out to not be the right person for the role. They were supremely talented, but people management proved to be an area of growth for them. The impact of this one area of weakness showed up on a consistent basis and eventually led to the decision to find a way to part ways with them. Unfortunately, this came at a time when they were navigating some personal needs at home. As their manager, I had real concerns about how this change to their career would negatively impact them personally given the timing. The decision was made to wait for them to navigate the needs of their personal life, return from leave, and then have the tough conversation with them then, which I did. It would have been easy to just rip the proverbial bandaid off and move on, but providing space for them to be able to deal with it at a time when they were more equipped to do so successfully and at a time that wouldn’t increase the stress they were already feeling, was what was right for the person on the other side of our business decision. We worked out a plan for them to continue working with us in a more limited capacity while finding new employment to help ensure they were able to land on their feet and not disrupt them personally or economically, and all were able to move forward in as positive a way as possible given the circumstances. I like to think that by being empathetic of what this person had going on personally, we were able to put the person first, while still doing what was necessary for the organization, leading to the most positive outcome for all.

How do empathetic leaders strike a balance between understanding their team’s feelings and making tough decisions that might not be universally popular?

This may not be the most popular opinion to your audience but it’s what I truly believe: the role of someone in my position is ultimately to ensure the ongoing success of the business first and foremost. Full stop. If the business goes away, so does every single job it creates — or can eventually create. At the same time, though, the company doesn’t exist without its people, so I think there is a healthy and necessary balance between the needs of both.

For me, the best way to do this is through transparency, candor, and honesty. As an organization, we strive to be as transparent as possible — sometimes I think to a fault — so that everyone understands the why behind the decisions we make. The same is true in reverse, too, though, we actively encourage transparency from our team as well, at all levels of the organization. I even have an open calendar invite where anyone can book time to grab coffee with me and talk about anything they’ve got on their mind. I think to be empathetic ultimately is to understand. To do that, we have to have open dialogue.

We’re not always going to agree. Not every decision I make will be a popular one. We’re not going to be all things to all people. I think that’s okay. The key is being open, and honest, setting clear expectations, and ensuring everyone understands one another as best we can.

How would you differentiate between empathy and sympathy in leadership? Why is it important for leaders to distinguish between the two?

I think that’s an interesting question. And I think both are very closely related to one another. To me, empathy is about putting yourself in someone else’s shoes and trying to understand their feelings and perspectives as if they were your own. Then, making decisions that impact them accordingly. Sympathy, on the other hand, relates more to providing emotional support to someone as they deal with hardships, but not necessarily feeling what they feel.

As leaders, empathy is more powerful because it builds genuine connections, builds trust, and promotes a positive work culture. It enables leaders to better understand unique challenges, leading to more effective support and decision-making that ultimately gets the best out of the team and does the best for the organization.

In contrast, sympathy is more detached, offering support without truly grasping the emotions and nuances of a situation. Leaders who distinguish between empathy and sympathy create workplaces where understanding and collaboration thrive, fostering more engaged and motivated teams.

What are some practical strategies or exercises that leaders can employ to cultivate and enhance their empathetic skills?

I’m not going to pretend I’ve got it all figured out — I don’t. But I do know things that help me with my team, and I learn new things every day as we grow. For me, it starts with actually caring. The authenticity of someone feeling as though you actually care about them is the most important aspect of deploying true empathy as a leader.

I took this for granted early in my career, and as a leader at Ammunition, I have worked hard to always ensure our people are at the heart of everything we do.

We want to build the very best organization for growth-minded individuals who want to do their very best work every single day, while being relentless about teamwork, inclusivity, and our dedication to ensuring the well-being of everyone on the team. To do that, we need to provide each member of our team with the very best place to do their very best work, regardless of who they are, where they come from, who they vote for, who they worship, what they look like, or who they love. To deliver on this promise, we need to deploy real empathy that can be felt across the organization, because that’s how we ensure we’ve built the most supportive environment we can for all involved.

How can empathy help leaders navigate the complexities of leading diverse teams and ensure inclusivity?

Ultimately, I think at the heart of diversity and inclusivity is actually caring about people for who they are. We have to acknowledge that we’re going to make mistakes, we might offend someone, and we will say the wrong thing, but if we first start by actually caring — building real relationships with those in our stewardship — then it’s my hope that the trust exists such that we can work together to overcome those missteps. I think it’s only when the trust isn’t there, that then, assumptions are made, the worst is assumed, and that’s when negative consequences can really come into play.

What’s your approach to ensuring that succession planning is a holistic process, and not just confined to the top layers of management? How do you communicate this philosophy through the organization?

I think Ammunition has built a real track record of cultivating and growing our own. I believe in merit over experience always and am not shy about betting on folks who may have less experience if the talent, potential, and desire are there. You can’t teach people to care, you can’t teach passion, but you can teach the work. Across all layers of our organization, you’ll find someone whose career has accelerated in their time with us — some even joining in entry-level positions and rising to VPs in the organization. We’re vocal about this too and highlight these accomplishments publicly so that it’s clear to everyone on the team why someone is rewarded so that they understand how they too can do the same.

Based on your experience and research, can you please share “5 Ways Empathy Will Affect Your Leadership”?

1. Relationships. I think first and foremost empathy leads to stronger relationships. It goes back to the notion of actually caring. Anyone can call themselves a “boss” and lead through authority. But as I told someone on the team recently, if you need authority to lead then you probably aren’t cut out to be a leader. Empathy, and good relationships, mean you’ll lead because others want to follow. The distinction between the two is very important.
2. Decision-making. Perhaps building on the point above, I think stronger internal relationships means being more in tune with the team, and subsequently being able to make better decisions — even unpopular ones — that the team can rally around. When we reopened the agency from being fully remote after COVID, we, somewhat arbitrarily, asked folks to come in on Mondays and Wednesdays and gave everyone a floating third day they could use at their discretion. For more reasons than one, this wasn’t overly popular but the chief reason among them was that the fluidity of the floating day made the in-office environment unpredictable. One could easily come in on a Friday and be the only person in the office. And if our real hope was connectivity, that worked against us. We were able to connect with the team on what works best for them and ended up arriving at a Tuesday-Wednesday-Thursday in-office schedule that was incredibly well received. And, to this day, I haven’t heard a single complaint about our schedule, and it’s actually proven to be something that helps our recruitment efforts rather than hinder them.
3. Conflict. I think that if you can check the box on good relationships, as well as connectivity with the team through better decision-making, you get better conflict resolution. Conflict will happen. Someone will upset someone. Leadership will make unpopular decisions. We’ll see the world differently from one another. That said, if there is a real sense of meaningful empathy, we can easily overcome those challenges together.
4. Morale. Continuing the build here, I think positive morale is the outcome of 1, 2, and 3 working together. As trust is built, communication is enhanced, and people feel heard and valued, and that can’t be anything but positive. I’ve seen it first-hand here at Ammunition as we’ve grown. Empathetic leaders create an environment where team members feel valued and understood. When employees feel that their leaders genuinely care about their well-being, I think they are more likely to be motivated, committed, and loyal to the organization. Who wouldn’t be?
5. Client satisfaction. When we build an organization that gets everything above right — or at least more right than wrong — we build organizations with better employee satisfaction and retention. That leads to clients feeling that same level of satisfaction and continuity, which in turn leads to happy clients. This, going back to the very first few questions, underscores the balancing act of doing what’s right for our people and our clients. If you nail the former, you’ll get the latter. I’ve seen it first-hand as Ammunition has for three years running had nearly 100% client retention — in addition to clients that have been with us since the very beginning and work with us to this day.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

I think that it’s important to care but to also be sure not to care too much. By that, I mean I believe as an employer, once we hire someone to join our team, the most important thing we can do is to protect that job to the best of our abilities. To me, empathy is a short road to patience, which means we can unintentionally give people the benefit of the doubt longer than is fair and more than is appropriate. I made a pact with my HR leader internally that if ever we are talking about the same employee more than three times for the same issue, we need to hit the brakes and have a meaningful discussion about how we are going to proceed: do we need to develop a performance improvement plan, or do we need to work towards parting ways. Either outcome is better than inaction, as inaction is far more likely to lead to negative outcomes than proactively dealing with an issue head-on.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

I take the role of employer very seriously. And by that, I mean job creator. The most sacred part of my job is ensuring the integrity of the jobs Ammunition creates for those who choose to work as members of our team. It doesn’t “keep me awake at night,” but it’s something I take great pride in. Never in my time being responsible for these decisions in 9+ years have I been responsible for layoffs, and I hope to keep it that way.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Call me sappy, but six years ago, I welcomed my first child into the world, and one more since then. Having kids made me an emotional person in ways I didn’t expect. With that filter in mind, I think if I could “start a movement,” it would be one that helped shine a light on the role employers play in the well-being of those who work for them. Earlier in my career, I wore working an 80-hour work week like a badge of honor and expected others to do the same. Today, I’m reluctant to send an email after 6 p.m. I often joke with folks on my team that I’d rather be home with my girls than sitting in a room with them… it’s delivered like a joke, but it’s true. And I think it’s true of all of us. I hope that we all have careers we enjoy and that enable us to live the lives we want to live, and I hope that as employers, we all focus on supporting those who work for us as best we can, providing opportunities to do our best work and lead our best lives. I don’t know if that constitutes a movement per se, but it’s something I’m passionate about.

How can our readers further follow you online?

LinkedIn — Jeremy Heilpern

Twitter — @heilpern

Instagram — @heilpern

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.