Eli Weiss on chasing curiosity, playing the long game, and how to be a good boss

Meet Eli Weiss, the Director of Customer Experience at OLIPOP.

I’ve known Eli for a while now and have loved watching his journey unfold, going from working at a flailing luggage brand (not Away!) to where he is now, a thought-leader on how to take care of your customers. Even better, he looks after his people like they’re his own.

Eli is curious and hard-working. He’s a trailblazer in the eCommerce and consumer space, someone who’s ahead on the trends or what’s “cool.”

So, here’s a more intimate conversation with him, where we cover all sorts of topics, like:

Growing up in an Orthodox Jewish family…

Being broke while traveling the world…

His guiding life principles…

How to think about customer experience differently…

+ why employees don’t give a sh*t about happy hours and ping pong tables.

Let’s dive in!

Tell us about your background. Where were you raised, and what were you raised on?

I grew up in an interesting world. I'm the 2nd of ten children raised in an insular Orthodox Jewish community. One idea instilled in me from a young age was to be a quick learner. “New” wasn’t scary; it was an opportunity to level up and grow.

As a teenager, I became fascinated with people. Ironically, as an introvert, the science around what makes people tick amazed me. I found myself reading books like Influence by Robert Cialdini or How to Win Friends and Influence People by Dale Carnegie. 

Travel was a way to accelerate learning about myself and the people around me. In my early teenage years, what started as road trips turned into traveling around the world when I learned about credit card points and miles.

At 21, I had no college education or work experience but a chip on my shoulder and an intense desire to change the world. I traveled all over Europe, staying at luxury hotels; meanwhile, I only had $400 in my bank account. Travel shaped how I see people.

Another thing I’ve always been fascinated with is Customer Experience. CX directly interacts with consumer behavior and human psychology, yet many brands were traditionally hesitant to invest in CX, as they did not see a clear “ROI” associated with it. As a generalist in my first four years at startups (touching everything from ops/logistics and investor relations to business strategy), CX felt like the most underutilized area of business, especially given the rising customer acquisition costs. So that’s where I decided to invest my skills.

You're a busy guy. What are your daily routines like?

As my days get busier, I look for pockets of time to do deep work. As a new dad, most of my mornings start early. I wake up around 6 AM and hang with my son for a while. Then, I make time for two things in the later morning:

1. Meditation and alone time

2. Deep work

My day is more meaningful when I create space for those things. I also generally avoid meetings until Noon EST, which works well since my coworkers are based on the west coast! 

And then, the afternoon hits, which is generally when my day descends into chaos… ha!

What's it been like for you to step into a leadership role at a time in your career when so much is changing in the workforce?

So much about leadership is understanding that you really do work for the people that report to you. The "great resignation" is really employees understanding that they can work from anywhere on almost anything, and it is your responsibility to make sure they feel like they are doing their best work while working on your team. 

As a leader, I am responsible for their growth, and I am responsible for keeping them inspired.

What are your guiding principles or mottos in life, from work to personal relationships?

Here are some things I try to live by:

1. Be a good person

This might sound silly, but it is rare. I often see people burn each other just to get ahead. While that might pay off in the short term, your name and reputation will be ruined.

2. Quality > quantity

I feel this way about my friends and also in business. I would rather have fewer close friends than a ton of not-so-loyal ones. I would rather have more loyal repeat customers than a massive group of ones that only buy something once In business.

3. Play the long game.

I’ve championed investing in great Customer Experience way before it was cool to (and we have a long way to go), and I deeply believed CX has a huge role to play in the long-term success of any business.

So much of customer service as a function is systematically broken. Where have you seen the most change in CX in your experience and where do you feel like brands are dragging the most?

To me, "the customer is always right" is inherently wrong, because it’s not about being right or wrong. It's about everyone having a voice, especially those who spend their money on a product or service. So, giving customers a seat at the table solves this, and having your CX team enable that voice is even better.

At large, we’ve seen customer experience endure a few rebrands since the days of "Customer Service.” At its core, CX has always been viewed as an entry-level job. 

But, as a role, it is often emotionally taxing without getting the credit it deserves. While Sales and Growth roles take home trophies and large bonuses, the front lines of the business often pay silly wages and are placed in the corner of the office.

That said, I believe companies are slowly shifting how they invest in CX. We’re a long way from where we should be, but we’ve made lots of progress!

The biggest opportunity for brands on the CX front is learning to collect and leverage data early on. Customers constantly tell you what they think about your product/experience, and brands have to listen and hold that feedback closely. It’s more difficult to do that whenn you outsource the CX function.

How do you think about building CX as a channel? Is there a playbook for it?

The difference between customer support (resolving tickets) and customer experience is the proactive nature of CX. CX is a sales channel, a research opportunity, and a retention strategy when done well 

You also need a team with resources. It's hard to see opportunity when you’re drowning in tickets. 

Here are a few things I focus on when building a CX team:

1. The who—Hire people who truly think differently and care deeply about others.
   

2. Empower those people—The bottleneck for great CX isn’t your employees or whether they can create or execute. It’s on the leadership side, bad management, and lack of empowerment.
   
   
3. On a tactical level, proactive CX is about looking at the customer journey from a holistic perspective and making sure you are meeting expectations on everything. From ad copy and website experience to shipping, delivery, and returns. 
   

4. Last, some of my CX core values are:

• Good CX is a marketing channel; allocate more spending to CX!
• Give the consumer a voice. Let them be part of decision-making because it’s pointless to make something folks don't want.
  

What's tired, what's wired, with respect to CX right now?

Tired: Spamming your customers with emails and texts to squeeze every last dime from them.

Wired: Creating segmentation to project the right message to the right folks at the right time.

You've said before that company culture isn't about happy hours or ping pong tables, but that it's recognizing accomplishments, aligned values, and so on. Expound on that…

Employee experience is something I am deeply passionate about. I firmly believe you can’t have great CX if you don't have great EX.

Folks who join startups give up on the easy and simple 9-5 for the ability to grow rapidly as their company grows. Having perks is great, but replacing human needs for perks isn’t right.

Here are some things I believe are important to give to your employees that will go a long way.

1. Recognition is free. Offer it widely. 

2. Give your team the ability to win  when you do.

3. Align on real values instead of weaponizing your core values. 

4. Take the time to understand where your team wants to become. Think about their future too.