A Letter To a Younger Eli (One Year into Yotpo)

Hi Friends,

Before kicking off this week, I want to take a moment to acknowledge the wildfires affecting the Greater LA area. To those impacted, my heart is with you, your families, and your communities. Please don’t hesitate to reach out if there’s any way I can support you during this time. I am thinking of you all.

Some long-time readers might remember a newsletter I wrote over a year ago titled “A Letter to a Younger Eli,” one of the more personal and poignant newsletters I have ever written.

Entering a new year and a little over a year since I made a massive career move, I have been thinking about what I have learned and what I would tell my younger Eli now.

The only difference is that I am now talking to the Eli of a year ago, not ten.

It will be personal, raw, and poignant. 🙃

Bear with me.

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Dear Eli,

You’re about to enter a year that will stretch you in ways you can’t imagine. Uncertain decisions, moments of doubt, and unexpected lessons will change how you see yourself and your work.

Here’s what I wish I could tell you before you jump in:

1. Trust Your Gut, Even When It’s Outlandish

You’re about to make what feels like the riskiest decision of your career: leaving the world of CX and Retention at some of the best DTC brands, where you’ve built your reputation, for a SaaS company that some of those same people openly dislike.

On paper, this move won’t make sense to almost anyone but you. But here’s the thing—you’re not chasing applause. You’re chasing something deeper: clarity.

Deep down, you’ve started to feel it. The brands you’ve worked with are successful, but you don’t feel like you’re leaving a big enough mark. It’s not about what others see in your job but what you need from it. And what you need isn’t validation or prestige—it’s a challenge that pushes you to grow and to give in ways you haven’t yet.

You’re going to doubt yourself, especially in those first few months. The questions won’t stop, and the results won’t come overnight. But you’ll realize soon enough that this decision—this outlandish, gut-driven leap—was exactly what you needed.

No one knows what you need better than you do. Trust it. Sometimes, the moves that seem impossible to explain to others are the ones that help you explain yourself to yourself.

2. CX Will Always Be Part of Your Life’s Work

Not too long ago, CX in ecommerce wasn’t taken seriously. It was a side note: an underresourced and underappreciated fire extinguisher department. Companies like Zappos were outliers, not the rule.

You worked hard to change that. You pushed CX into marketing conversations, made it a competitive advantage, and showed how it could transform retention and brand loyalty.

And it worked. Today, some of the best brands in the world, like Kith and HexClad, are investing in CX leaders, recognizing them as strategic partners. You helped lay the groundwork for that shift, and the impact is more significant than you might realize.

CX can be your life’s work, even if it’s not something you work on every day. The empathy, intentionality, and connection you built through CX are skills you’ll carry into everything you do.

You worked to start a movement around CX, one that continues even as your role in it evolves. Be proud of the mark you’ve left and the doors you’ve opened.

3. Kindness Over Ego in a Hostile Industry

The world you’re playing in isn’t short on ego or hostility. For all its innovation, DTC often feels like a stage for public takedowns and private one-upmanship. It would be easy to get swept into the culture of clout and competition, but you won’t. You’ll choose empathy, humility, and kindness instead.

You will build spaces where empathy thrives. The dinners you co-create for empath leaders will be spaces for people who, like you, believe kindness is a strength. The retention and CX online communities you nurture will grow into places where collaboration replaces posturing, and sharing ideas is the norm.

This path won’t come without costs. You’ll lose seats at some tables, miss opportunities to “play the game,” and probably upset a few people by refusing to engage in the industry’s more toxic traditions.

You won’t change the DTC world overnight, but you’ll plant seeds. You’ll show that kindness isn’t naive and humility isn’t weak. The communities you help build and the respect you’ll earn will prove that a different way is possible.

4. Growth Isn’t Always Linear, and That’s Okay

You’ll have days where everything clicks, and you feel unstoppable. Then, there will be days when the progress feels invisible, every decision feels second-guessed, and you wonder what happens next.

The truth is, the growth you’re chasing isn’t linear. It’s messy, unpredictable, and filled with moments that don’t make sense until much later. The year ahead will stretch you in ways you can’t measure in a single moment.

Some of the biggest wins won’t feel like wins until you look back and see how far you’ve come. Progress often looks like chaos up close but clarity from afar.

The SaaS job you’re taking will challenge you, not just in your role but in your ability to convince those around you of the long-term vision when the short-term doesn’t always deliver immediate payoffs.

The moments that feel the hardest will teach you the most. Even the setbacks will be part of the story that brought you where you needed to be.

5. Relationships > Lazy Networking

You’ve always preferred depth over breadth. In an industry often driven by metrics and transactions, you’ll find that the real breakthroughs come from genuine human connections.

You’ll meet people who inspire you, who challenge you, and who make you question what you thought you knew. Some will become mentors, others collaborators, and a few might even become lifelong friends.

The dinners, the late-night conversations, and the moments of shared vulnerability will teach you far more than any keynote or panel ever could.

In the year ahead, don’t chase followers, titles, or speaking engagements. Seek out the people who care as deeply as you do about creating something meaningful. Relationships take time and effort, but they’ll shape your career and life in ways you can’t yet imagine.

That’s it for now, Eli. Keep learning, keep growing, and keep trusting yourself. The best is yet to come.

Love you,
Future Eli

That’s it for this week!

Cheers, 

Eli 💛

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

I know you will love this.