The Greatest Leaders in Ecom

Hi Friends,

There's been a ton of chatter lately about how AI is eating the world, and I, for one, have been doing my best to stay on the AI overlords' good side before AGI decides to show up.

But as I’ve watched the buzz unfold, one thing keeps coming up for me: how crucial empathetic leadership is right now, maybe more than ever?

Especially in CX and retention—imagine seeing your boss post on LinkedIn about how AI is coming for CX teams first or how the future of email and SMS is AI-first. What does that do for your team’s mindset?

Call me old-fashioned, but I genuinely believe people who feel empowered and valued will stick around—even when faced with a massive, world-shifting leap in technology like this.

So, today, I want to take a different approach. I want to share a few personal stories of leadership moments that have stuck with me–stories that seemed pretty ordinary at the time but have lived rent-free in my mind ever since.

Shall we?

Let’s do it.

This week’s newsie is brought to you by Siena AI!

Imagine if your brand became the #1 seller on TikTok Shop—sounds amazing, right? But with that success comes unexpected challenges. For Comfrt, their ticket volume tripled in just three months, putting massive pressure on their CX team. Instead of scrambling to hire more agents, they launched an AI Agent with Siena in just 2 weeks, handling 65% of the load seamlessly. If you’re an apparel brand dealing with this too, you need to hear how they did it. Sign up for the webinar happening today (you'll also get the recording after)—it’s one of those you can’t afford to miss moments.

That’s why, this week, I’m spotlighting Siena AI, the Empathic Autonomous AI Agent built for commerce. 

Here are 3 things that make Siena stand out:

• AI That Build Relationships: Learns from your best agents to create genuine connections, not just close tickets.

• One Brain For CX: Siena is unifying the CX stack - from pre-sales to support to insights. No more fragmented customer journeys.

• Industry-Specific AI: Purpose-built for consumer brands, learning from millions of real interactions to deliver what horizontal AI can't.

Some recent cool reviews on the success stories:

• Comfrt: "Brooke is one single AI and yet solving more tickets in a week than our human team. We have faster response times, faster resolution times, higher customer satisfaction, and that's huge to say." 

— Kristen McClure, Head of CX at Comfrt

• Fuel Meals: “It is the easiest, most human, lightest lift AI tool that covers every CX channel you need." 

— Anya Kelly, Founder of Ciao CX

• MUD/WTR: “What stood out with Siena is that we're in control of everything. We can determine the tone of voice, and give her her own name and persona to reflect our brand personality and values. Our CSAT score went from floating around a 4.5, to now every week being consistently at 4.8 and above.”

— Sara Colon, Customer Support Manager

Q1 is the perfect time to rethink your CX strategy and set your brand up for success this year. With Siena, you’re not just adding automation—you’re building a smarter, scalable CX foundation. Their team works closely with you to launch AI Agents tailored to your brand in record time. If you’re ready to make 2025 the year your CX truly levels up, reach out to Lisa and the Siena team to see how they can help. 

Also, they are offering my readers 20% off for the first year. 

Leadership That Sticks With You

In general, OLIPOP was different. Everything about that company was thoughtful and intentional through and through—from the product to the marketing and, of course, the culture.

It was the week before BFCM at OLIPOP, the most chaotic time of the year. The kind of week where the stress is palpable, and it feels like you’re barely keeping the wheels on.

Everyone was heads down, grinding through the madness, making sure our new seasonal flavor launch was ready, along with prepping for the most hectic sales days of the year.

And honestly, it felt like no one was noticing how much effort was going in or what impact it was actually having.

Then, a 45-minute meeting popped up on the calendar. In the middle of that week. Great—another meeting we didn’t have time for.

But instead of the usual rushed updates or strategy talk, our co-founder got on the call and spent the entire 45 minutes shouting out every single person on the team. One by one, he called out specific contributions we’d made—down to the details—and explained how they’d impacted the business.

Not vague “great job” kind of stuff. He knew exactly what each person had done and tied it back to real results.

Even in the moment, I remember thinking: Damn, this is different.

Five years later, I still think about that call. Not because of the praise but because it showed how much leadership matters—especially during the hardest, most chaotic times.

It wasn’t a big, flashy holiday gift. It was a leader taking the time to show he saw us, that the work we were doing wasn’t going unnoticed, and that it was making an impact.

That’s the kind of leadership people stick around for. You don’t need to overcomplicate it. Just be intentional. Pay attention. Let your team know you see their effort and value it.

It’s such a simple thing, but it makes all the difference.

What Bobbi Brown Taught Me About CX

When I joined Jones Road Beauty, I expected the usual from a founder like Bobbi Brown—busy, legendary, and juggling a million things. I figured she'd swoop in for the big-picture stuff and leave the rest to the team. But what I saw was entirely different—and it stuck with me.

Every product launch was an event. Bobbi would gather the whole team—CX, marketing, operations, you name it—and take the time to break down everything. 

She’d show exactly how the product worked, tell us why she created it, and even share personal stories behind it. She’d demo it herself, invite team members to try it and answer every question. And she didn’t stop until every person in the room got it—not just the product itself, but the story that made it special.

For the CX team, it especially gave their work weight. They weren’t just troubleshooting issues or answering angry emails—they were now part of the bigger story. They understood how to speak about the product like experts, not just representatives. And that feeling of ownership and connection showed up in every customer interaction.

Seeing Bobbi dive deep into her zone of genius—her passion for makeup and storytelling—reminded me how powerful it is when leaders make people feel like their role really matters. It wasn’t just about the product; it was about making sure every customer felt the passion and purpose behind it. 

That’s a lesson I’ll never forget.

What Yotpo Taught Me About Leadership That Actually Cares

When I joined Yotpo, I walked into a company that had been thriving for thirteen years—over a thousand employees, offices around the world, and a founder who, at least on paper, should’ve been focused ten years ahead, playing solely the visionary role. 

I came in to help take Yotpo into its next chapter—a version closer to the market, sharper, more aligned with brands—and honestly, I expected the CEO, Tomer, to glance at a deck, nod, and let the team handle the details.

What I saw over the past year couldn’t have been further from that.

Tomer spent hours upon hours speaking directly to the people who matter most: agency operators, brand founders, customers who rave about us, and yes, even those who churned. He wanted to know every friction point, every blind spot, every untapped opportunity.

It’s not just a surface-level thing, either. Tomer’s on sales calls, digging into deals. He jumps into CS escalations—not for optics, but because he truly believes in leading by showing up. And what happens when the founder of a company with a thousand employees is willing to be on the front lines?

Everyone else feels like their work actually matters.

It sets the tone across the board: sales reps feel empowered to fight for every deal, CS teams go above and beyond to resolve tickets, and no one’s coasting on autopilot because they know the person at the very top cares. And it’s not theoretical—he’s right there, putting in the same energy.

The lesson? You can’t fake giving a sh!t. And when your team sees that kind of commitment, it trickles down into everything. Because when your people know they’re not just a cog in the machine, they show up differently.

Make employees feel like cogs in a machine, and they very well might quit the machine before you bring robots to take them over. 🙃

That’s it for this week!

Any topics you'd like to see me cover in the future?

Just shoot me a DM or an email!

Cheers, 

Eli 💛

P.S. Looking for inspo on your next email/sms campaign?

I know you will love this.