Episode 469: Authentic Selling in an AI-Driven World: Building Trust, Culture, and Human-Centered Sales with Jeff Kirchick

Jeff Kirchick | 00:00
There are a lot of things it could mean for many people, often as a euphemism for social selling—social media and things like that. But for me, my entire ethos has been about presenting an honest version of yourself.

Intro | 00:13
Welcome to the Making Sales Social podcast, featuring the top voices in sales, marketing, and business. Join Brynne Tillman and me, Bob Woods, as we bring you the best tips and strategies our guests are teaching their clients so you can leverage them for your own virtual and social selling. Enjoy the show.

Brynne Tillman | 00:39
Welcome back to Making Sales Social. I’m Brynne Tillman, and today we’re diving into the intersection of authenticity, storytelling, and sales leadership with someone who lives it every day—Jeff Kirchick. Jeff is the VP of Sales at Zorro, a fast-growing healthcare benefits company helping employers offer truly personalized health plans. He’s also the author of Authentic Selling: How to Use the Principles of Sales in Everyday Life, a book that challenges traditional sales thinking by putting authenticity and human connection at the center of the conversation. From leading startups to successful exits to helping sales professionals rediscover the real meaning of influence, Jeff brings a refreshing perspective on what it takes to sell with integrity and purpose. Jeff, welcome to the show.

Jeff Kirchick | 01:32
Thank you. I appreciate it and am looking forward to our conversation.

Brynne Tillman | 01:35
Me too. I’m really excited to chat with you about the authentic side of selling—that’s my favorite topic of all topics. Before we jump in, we ask all of our guests the same first question: What does Making Sales Social mean to you?

Jeff Kirchick | 01:55
It can mean a lot of things to a lot of people, often as a euphemism for social selling—social media and things like that. For me, my whole ethos has been about presenting an honest version of yourself, which is critical to authenticity, especially in an age of AI and automation. Making sales social means building authentic relationships—not only with the people you sell to, but also with the people you work with.

If you’re able to be vulnerable and have authentic conversations about what really matters to you and what’s happening in your world, you can build incredible relationships. Some customers I worked with years ago—I’m still close with them. I follow them on Instagram, we talk, I know the names of their kids. At the end of the day, that’s what makes it rewarding. You get to make new connections, help people, and genuinely feel good about it. Making sales social is about having a real social life with the people you work with.

Brynne Tillman | 03:05
I love that answer. In a world of AI, automation, and connect-and-pitch, leaning into relationships makes all the difference. I also love that it doesn’t have to be business all the time—you can talk about your kids or shared interests.

Your book, Authentic Selling, reframes sales as part of the fabric of our everyday lives, not just business. What first made you realize that authenticity could be a sales strategy, not just a personal trait?

Jeff Kirchick | 04:02
Ironically, it came from my lack of formal sales education. I worked mostly in early-stage startups that were pretty unstructured compared to larger tech companies. I wasn’t put through formal sales processes early in my career, so I relied on things like working hard or having a good personality. That helped me get by at first.

As my career progressed, I found myself selling large contracts to Fortune 100 companies without formal enterprise sales training. I wasn’t running MEDDICC or any structured qualification frameworks. When I looked back, the common thread in all of those deals was strong relationships within the organization. More importantly, it was trust. People knew I was honest about the good, the bad, and the ugly.

A slightly controversial example I use is Larry David. He’s not the most likable person, but you always believe him because he says what’s on his mind. When someone speaks, and you believe them, their words matter. Consistency between what you say and what you do builds credibility.

I also wrote the book during the pandemic, a politically charged time. I noticed how quickly people attacked each other. As a salesperson, you learn that the only way to influence hearts and minds is through empathy and listening. Authentic anger doesn’t change minds. Sales skills—empathy, listening, understanding—are critical for building better relationships, not just closing deals.

Brynne Tillman | 07:01
That resonates. My mom taught me something years ago that completely reframed how I think: Look at your behavior and ask whether it’s working toward or against your goal. What do you want at the end of this interaction, and is what you’re doing helping you get there—or isolating people just to be right?

Jeff Kirchick | 07:50
I have a similar expression: Am I working toward my values? It’s the same idea. It’s hard, though. There have been times when I wish I’d handled situations differently—when frustration or anger took over. Asking whether my reaction aligns with my values or helps achieve my goal has always helped ground me. I love that expression.

Brynne Tillman | 08:24
I love the values piece—it’s not just about goals, but about how you live. You’re a sales leader, so how do you apply authenticity at scale? You’re managing a team with metrics, goals, and pressure. How do you balance hitting numbers while genuinely showing up to help people solve problems?

Jeff Kirchick | 09:10
It’s a great question. Some of it may sound overly simple, but I try to show up at work the same way I do everywhere else. I try to be myself and invite the team to be open and vulnerable. At an onsite, we did an exercise where everyone shared their “why”—what they want for themselves in life.

It may seem counterintuitive, but I think it helps to minimize the drama around work. If you tell people the sky is falling because you missed a number, they won’t believe you. There was life before this job, and there will be life after it. Being honest about that matters.

I joke with my team—if something goes wrong, I’ll say, “Remember, we’re just specks of dust in the universe anyway.” It’s a bit of a running joke, maybe even a little Buddhist, but there’s truth to it. You may lose a deal, but life goes on. Fixating on it isn’t productive.

Everyone has personal stakes beyond the nine-to-five. Work matters—it’s how we get what we want in life—but honesty builds trust. When you do need to be serious or apply pressure, people respect it because they know you’re not always operating in that mode.

Do I do this perfectly? Absolutely not. I make mistakes every day. But being honest about that makes you relatable. A leader who never self-reflects or self-deprecates is hard to connect with.

Brynne Tillman | 12:02
That’s powerful. It reminds me of a close friend who was an ER nurse before moving into medical software leadership. During a crisis, she’d say, “It’s software—no one is bleeding out.” If no one is going to die from this, we can step back, stay calm, and solve the problem.

Jeff Kirchick | 12:49
I’ll admit this—I was at Disney World with my wife and our almost two-year-old daughter a month ago, and I was glued to my phone during a busy work period. My wife said, “You’re replaceable at your job, but you’re not replaceable here.” That hit hard. She was right. I put the phone away and focused on being present.

Brynne Tillman | 13:20
I love that so much. Do you find that showing up this way encourages your team to be more vulnerable and authentic?

Jeff Kirchick | 13:36
Absolutely—100%. We’re a remote team, so culture is critical. If you don’t have a strong culture, it’s the first thing that makes people consider leaving.

When mentoring younger professionals, I always tell them the most important factor in choosing a company is the people. They will make or break your experience. You might end up working on something you never expected, but if the people are great, you’ll enjoy it far more than working on something you’re passionate about with a bad team.

You need true buy-in—not just to the company, but to one another. That’s foundational. If you don’t get that right, everything else erodes from there.

Brynne Tillman | 14:47
How are you balancing leveraging AI in a positive way? Are you empowering your sales team to use it? Is that something important to you, and how are you leveraging AI without sacrificing trust and authenticity?

Jeff Kirchick | 15:08
AI has been the number-one topic on people’s minds for the last few years, and it’s something I’ve been thinking about for quite a while. It’s one of the reasons I wrote my book. About five years ago, I saw this coming and believed that humanity would become more important than ever in the age of AI.

Right now, most AI use cases are productivity-driven. Down the road, that may change. Mark Roberge of Stage 2 Capital wrote an article about the phases of AI implementation, where eventually you may have AI buyers and sellers on both sides—agents representing people on each side of the transaction. But that’s phase two or three.

We’re currently in the phase focused on productivity and automation. The goal of AI today should actually be to increase the human element and authenticity. Most sellers are probably spending only 10–50% of their time interacting with customers. The rest is spent updating CRM systems, reviewing call transcripts, or figuring out follow-up actions.

If AI can automate research, update CRM records, and help codify key points, sellers have more time to spend with customers. That’s the direction we’re moving in.

I know some organizations are asking how to remove sellers entirely—whether they even need SDRs or can automate everything with chatbots. That’s not something I aspire to do. Our industry is highly relationship-driven, and we have about 50 competitors. One of the deciding factors for customers has to be the people they work with.

There may be different applications for more transactional or down-market sales, but this is how we’re thinking about it today.

Brynne Tillman | 17:31
I love that. I do think customer service will be the first area to go. I had an experience where I called customer service and didn’t realize for five to seven minutes that I wasn’t speaking to a human. I was blown away. It knew everything about my account almost immediately, and there was no wait time. I can absolutely see customer service being the first role AI takes over.

Jeff Kirchick | 18:22
I used to work in the call center space for a long time, and that’s exactly what they’ve been trying to do. Many of those roles are measured by how effectively they prevent customers from speaking to a human. That effort has been going on for decades. It stands to reason that the same thing will happen in software companies.

Brynne Tillman | 18:52
It’s frustrating today because we want to speak with a person, but there will come a point where talking to a person will be more frustrating than talking to AI. That’s when the shift will really happen.

However, it’s still engineered empathy. While there’s value in that—AI doesn’t emotionally react no matter how upset a customer gets—engineered vulnerability isn’t real vulnerability.

Jeff Kirchick | 19:37
Exactly. And it’s interesting because the brands people talk about are the ones with real human touch. Chewy is a great example. If someone loses a pet, Chewy has been known to send handwritten condolence cards or flowers.

That matters because losing a pet is like losing a family member. That kind of response is very different from an automated message saying, “We’re sorry for your loss.” It’s those human moments that create strong emotional attachment to a brand.

Brynne Tillman | 20:34
And there’s no ulterior motive. You’ve already canceled because your pet passed away. It’s just kindness. That’s real empathy, not engineered empathy.

Jeff Kirchick | 21:22
Absolutely. Even with simple things—if an order gets lost, they replace it and tell you to keep the original if it shows up. Other companies would demand it back. That kind of generosity really lands with consumers.

Brynne Tillman | 21:41
I love that, especially in the retail and dropship world. It’s not even a complex sale, yet it’s powerful.

You lead a team, and part of leadership is succession and growth. For leaders building trust-first, authentic cultures, how do you hire for that? How do you interview for authenticity and long-term growth?

Jeff Kirchick | 22:54
There are a few ways to approach it. First, build a scorecard around the values you care about and identify which answers align with those values. You can turn it into a science.

For example, honesty is very important to me. I’ll ask candidates what they need to work on professionally. Some people give a thoughtful, honest answer and even explain how they’re addressing it—that’s what I want to hear. Others give a disguised positive, like saying they work too hard. That’s actually a disqualifier for me because it shows a lack of honesty.

Accountability is another core value. I’ll ask about a mistake they made and listen for whether they take ownership or shift blame. Those responses tell you a lot about alignment with your culture.

Brynne Tillman | 24:17
You can train product knowledge and sales methodologies, but can you train authenticity and empathy?

Jeff Kirchick | 24:33
Yes, you can. The key is helping people detach from outcomes. Everyone is capable of being authentic, but what pulls them away from that is being overly attached to getting something in the moment.

If people can detach from the outcome, they can relax and be themselves. That’s when authenticity shows up.

Brynne Tillman | 25:06
I had no idea how aligned we were before this conversation. We say, “Detach from what the prospect is worth to you and attach to what you’re worth to the prospect.” That feels like a perfect way to bring this home.

What question should I have asked you that I didn’t?

Jeff Kirchick | 25:30
Where is AI going next?

Brynne Tillman | 25:38
So where is AI going next in sales?

Jeff Kirchick | 25:40
You’re going to see more facial recognition and contextual analysis. With conversational AI and video tools, the next phase will include body language—detecting nervousness, excitement, or even deception.

Brynne Tillman | 26:03
I use Sybill as a note-taker. It already tracks nods and smiles. We’re almost there.

Jeff Kirchick | 26:14
We’re very close.

Brynne Tillman | 26:17
To me, Sybill is the most incredible sales tool. It’s built specifically for sales coaching. Everyone has tools like Fathom or Otter, but this one is different.

Thank you so much for joining us. If someone wanted to connect with you or explore working with you, how can they reach you?

Jeff Kirchick | 26:52
My website is jeffkirchick.com. There’s a contact form there—that’s the best way to reach me.

Brynne Tillman | 26:58
Thank you so much. I truly enjoyed this conversation. I had several mic-drop moments, and I know our audience will too. To all our listeners, when you’re out and about, don’t forget to make 

Outro | 27:18
Thanks for watching. Join us again for more special guest instructors bringing you marketing, sales training, and social selling strategies that will set you apart. Subscribe to get the latest episodes of the Making Sales Social podcast. You can also listen on Apple Podcasts, Spotify, Amazon Music, and other platforms. Visit our website, socialsaleslink.com, for more information.