00:00   Traci Chernoff

Hi everyone, welcome to Leading the Frontline, sponsored by Legion. Thank you so much for being here — and if you haven’t yet, don’t forget to rate, review, and subscribe wherever you’re catching this episode.

We have a fabulous episode for you today, and I think you’re going to love hearing from this particular person. Whether you’re watching or listening, you’re in for a great experience — which is something we always guarantee here at Leading the Frontline.

Let me introduce you to Ryan Holm, the Divisional Vice President of Retail Innovation and Operations at Helzberg, where he leverages his firsthand knowledge of the frontlines to serve as a voice for innovative technology, new partnerships, and process improvements. With eleven years of experience in retail fine jewelry, Ryan has held leadership roles at Signet Jewelers and Helzberg. Previously, he spent a decade in the quick service restaurant industry, managing a franchise of Dunkin’ Donuts and Baskin-Robbins locations.

Ryan is known for bringing an analytical and practical approach to store teams and a deeply human approach to developers. He often serves as a translator between developers and end users, helping ensure that both parties better understand, appreciate, and respect each other’s roles. He ensures developers know what to build and stores understand how to use new tools to achieve their goals. He focuses on ensuring that his organisation incentivizes behaviors that lead to desired business outcomes — and that everyone throughout the organisation is aligned with a shared vision and rewarded for success.

This bridge-building role has led Ryan to frequently participate in speaking engagements and case studies, and he’s quickly gained a following on LinkedIn. Outside of work, Ryan enjoys running, wilderness backpacking, and good food, and is passionate about technology being used to better humanity.

Ryan, welcome to the podcast!

02:08   Ryan Holm

That was quite the intro. Thanks, Traci.

02:11   Traci Chernoff

You’re welcome! This is your life — and I think it’s wonderful to hear it read back so you can reflect on everything you’ve accomplished.

02:25   Ryan Holm

Sometimes hearing your retail career journey spelled out like that feels foreign, because I think most of us in retail didn’t really have a plan to go into retail. Things just happen and evolve along the way.

02:37   Traci Chernoff

So true. As a former retailer myself, I can totally relate. You just kind of realise, “Wait — I do like this. Maybe there’s something to make of this career.” And then you just keep going. It’s either you love retail, or you can’t do it.

02:58   Ryan Holm

It’s a sticky industry, absolutely.

03:01   Traci Chernoff

Totally. Here at Leading the Frontline, there are two questions I always start with for every guest — and you’re no exception. The first, which is my favorite: what was your very first hourly job?

03:30   Ryan Holm

I love that question. My first hourly job was at Dunkin’ Donuts. I was 16, and I wanted to buy a car but had no job. There was a Dunkin’ Donuts opening about three-quarters of a mile from my childhood home, and while it was still being built, I would walk there on a weekly basis and knock on the back door trying to turn in an application. I was the last hire — they basically said, “Show up on this date for training.” I showed up in jeans and got sent home because no one told me the dress code.

04:10   Traci Chernoff

Love that! Thanks, HR — I can say that because I’m in HR. But you’re definitely not the only person who’s been there: you’re eager, you know you need money to buy a car, you do everything right to get the job — and then you get sent home on day one. At least you were prepared to come back!

04:50   Ryan Holm

It all worked out. I came back the next day in khakis, got my uniform, and all was well. And I’ve since learned: always discuss the dress code during the interview, or whatever form the interview takes.

05:06   Traci Chernoff

That’s so symbolic of what leadership can sometimes look like — someone comes in with clear expectations based on what they were told, only to find none of those expectations were actually communicated. That’s on the leader.

05:36   Ryan Holm

It feels a little like foreshadowing for the rest of my career, where communication has become increasingly important.

05:41   Traci Chernoff

Absolutely. And even as technology advances, we still have those same basic human needs for two-way communication. Would you mind sharing a bit more about your background and what ultimately led you to your current leadership role?

06:16   Ryan Holm

It’s always hard to summarize, but I spent ten years at Dunkin’ Donuts. I started as an hourly employee, graduated high school, was offered a store, and said, “Thanks, but no thanks — I’m going to college.” They mentioned tuition reimbursement, and I said, “Sign me up.” That became my job through college. By the time I left, I was overseeing 13 stores in Northeast Ohio.

At 26, I was at the top of what I could do within that franchise, and I knew I wasn’t done growing. So I pivoted — and I happened to be in the backyard of one of the largest retail jeweler headquarters in Akron, Ohio. During my interview, the hiring manager looked at my resume and said, “Oh, so you’re moving from sprinkles to sparkles.” That tagline just works.

I’ve now had a ten-year career in jewelry. A pivotal early moment was watching associates sell engagement rings and feel immense satisfaction — and realizing I experienced it differently. I had a bit of imposter syndrome at first. But what really drove me was identifying processes that could be improved. If I could reduce the administrative burden on people who are genuinely gifted at connecting emotionally with customers, I could give them more time to do what they love — and that gave me the same sense of fulfillment I saw in them. Now my role is focused on making leaders’ lives more efficient.

08:46   Traci Chernoff

That’s amazing. And I have to give credit — both to you for recognising those transferable skills, and to the interviewer for seeing them. So much potential is missed when leaders are too narrowly focused on specific background requirements. When you can identify transferable skills regardless of industry, you unlock something really powerful.

10:04   Ryan Holm

What’s interesting about retail jewelry is that people often come in thinking they don’t know enough about diamonds. And there is a vast world of gemology and metallurgy you can explore — but jewelry knowledge doesn’t sell jewelry. Google can probably answer those questions better than most gemologists. What sells jewelry is the ability to emotionally connect with someone on multiple layers: getting to know them, understanding their love story, learning about the recipient — and then using a little knowledge to connect that story to a product.

10:57   Traci Chernoff

It’s all about the relationship. I love that. And it makes me curious about your leadership style — how would you describe it, and how has it evolved from sprinkles to sparkles?

11:22   Ryan Holm

My boss has a phrase I’ve always appreciated: things should always be on a “low simmer.” Not boiling over, not sitting tepid — just a constant sense that something’s happening, something’s building. For me, that’s meant staying focused on what’s next: succession planning, the idea that our best days are ahead of us. And consistently focusing on what matters most to the people in my charge.

11:57   Traci Chernoff

I love that. And it brings me back to the last line of your bio — that you’re passionate about technology being used to better humanity. What does that mean to you?

12:20   Ryan Holm

I believed that long before technology was part of my career. Eventually those two worlds — my hobby and my work — became one and the same. Right now it’s a complicated conversation because of AI. There are people who believe AI will save humanity, and others who are deeply skeptical. But I think long before the AI era, even something like a Palm Pilot — being able to organize your life without carrying paper around — was a small example of technology making things better. I’ve always believed in that potential.

13:28   Traci Chernoff

Any tool, used well, can be transformative. And it’s how we use new technology that can really set us apart, whether in retail, hospitality, or any other industry. Throughout your career, have there been any hard lessons — anything learned the difficult way, in leadership or otherwise?

14:32   Ryan Holm

The biggest lesson isn’t technology-related. It’s about taking the time, before any decision, to think through each individual on your team — even briefly — and consider how they’ll react to a change. Is this fair to them? How do they need to hear this message? As my leadership scope has grown, it’s easy to focus on the more vocal people and overlook quieter but critical contributors.

There was a specific time I left out a key player in how I communicated a change. Thankfully, they were honest with me about how it affected them. I had to sit with that, acknowledge they were right, own my mistake, and do what I could to make it right. The responsibility of having people in your charge — it stays with you.

15:46   Traci Chernoff

Leading people is not easy. And individual contributors face similar challenges — it’s all about how you influence those around you. As scope and scale grow, it gets harder to stay connected to what it feels like to be on the receiving end of a message. Thinking about your own team — is there something they do differently that sets them apart?

16:46   Ryan Holm

I think what’s different at Helzberg is a real commitment to aligning incentives so they work for the customer, the associate, and the company — all three at once. That alignment has led to incredible tenure. I’m ten years in and I’m often the newest person in the room. My boss has been with Helzberg for 36 years. When we hosted the first customer sponsor event at Legion CAB, the store manager who hosted has been with Helzberg for 29 years and will celebrate 30 next year. That tenure is a genuine differentiator.

17:48   Traci Chernoff

That’s remarkable. Decades of experience at one company is something truly special. What drives that kind of tenure — is it the culture, growth opportunities, the nature of the work?

18:23   Ryan Holm

There are a few facets. First, I’ll give credit to the industry itself. Jewelry is a unique subset of retail — the customer experience is elevated. You can have a great experience buying jeans, but you probably won’t remember that interaction in five years. You don’t forget the person you bought your engagement ring from. Those lifelong relationships help retain talent naturally.

There’s also the environment — being in a mall, everything behind cases, in control of the experience, celebrating love every day. That’s meaningful work. And culturally, Helzberg genuinely rewards and celebrates tenure. As both an American Gem Society member and a Berkshire Hathaway company, there’s a real focus on doing right by customers and associates. When that alignment breaks down, it’s the fastest way to lose people.

20:03   Traci Chernoff

Amazing. Shifting gears — are there any trends shaping the future of frontline leadership or team performance that you’re watching closely?

21:51   Ryan Holm

AI is the obvious one — but what I find fascinating is that AI is becoming less of a buzzword and more about practicality. For a while, solution providers were tagging “AI-first” onto everything just to seem relevant, and executives were essentially saying, “We want AI — we’re just not sure why.” We’re past that now. People want to understand where AI actually provides value, not AI for its own sake. That makes this year, and probably next, really exciting: sorting through the noise and identifying the real, meaningful applications.

23:02   Traci Chernoff

There’s nothing more sacred than the time a frontline manager or employee gets to spend with a customer — so getting any of that time back is always valuable. Last question: what is the best advice you’ve ever received and continue to live by?

23:36   Ryan Holm

It comes from a book: The Ideal Team Player by Patrick Lencioni. The premise is that the best teams have three qualities in every member — humble, hungry, and smart, where “smart” means emotionally intelligent and self-aware. I’ve used those three traits throughout my career to build strong teams and navigate difficult dynamics. What’s powerful about it is the shared language it creates: when something’s off, you can identify which of the three is missing and work on it together. It’s helped me in some of the most challenging team situations I’ve managed.

24:43   Traci Chernoff

I love that — and I may need to read that book myself. Humility especially stands out to me. When it’s missing, it’s very apparent. When it’s present, everything just works. The fact that you recalled it so quickly says a lot about how central it is to your thinking.

25:22   Ryan Holm

Whenever I find myself frustrated, or I can tell others are frustrated with me, I back up and check myself against those three traits.

25:36   Traci Chernoff

That’s a great practice. And last but not least — where can people follow you, connect with you, and see your work?

25:57   Ryan Holm

LinkedIn is the best place. And the other way to find us is to visit a Helzberg Diamonds store — we have 160 locations nationwide. We actually have two beautiful new concept stores opening: one at the Dallas Galleria Mall, and one at Roosevelt Field.

26:17   Traci Chernoff

Roosevelt Field is one of my local malls — I will absolutely be visiting! Ryan, if you’re ever paying a visit to the store, let me know. I’m on Long Island.

26:26   Ryan Holm

Wonderful! For NRF, we’re actually trying to organize a store tour, so maybe that’s the moment.

26:32   Traci Chernoff

You should definitely do that — Roosevelt Field is a fantastic mall. Ryan, thank you so much. It’s been a real pleasure getting to know more about your career, your journey, and your perspective. I’m sure all the listeners are going to love connecting with you on LinkedIn or visiting one of those 160 stores. And for everyone listening — don’t forget to rate, review, and subscribe wherever you’re catching this episode. Ryan, thank you so much for your time.

27:08   Ryan Holm

Thanks, Traci.