The Eli Weiss Playbook: How to Optimize CX and Retention

Eli Weiss is the Senior Director of Customer Experience at Jones Road Beauty. Eli has spent the last 8 years building and operating early-stage startups.

He is particularly known for his work around Customer Experience and Retention

at DTC brands such as OLIPOP and Simulate (NUGGS).


We sat down with Eli to dive into his deep domain expertise. We cover

topics including:


  1. How startups can launch early retention efforts

  2. His KPIs and how he implements them

  3. Why data is as the core of great CX

“Ultimately, I find data is the most crucial component of great CX. To do my job well, I’m consistently exploring how I can leverage the numbers to put effective changes in place that will genuinely help our customers.”



Structuring Your Startup for Early Customer Wins

In the earliest stages of a company, regardless of category, CX is

typically handled directly by the founder. It’s a great move, says Eli,

since you’ll intimately understand what is or isn’t functioning up to snuff

within your business.


But once customer support needs stretch beyond your bandwidth, Eli also

strongly advises against outsourcing CX labor while you’re scaling.


Instead, consider keeping your CX efforts internal, in order to maintain

the most accurate possible insight into what’s thriving and what’s breaking

as the company grows. Unfortunately, this valuable insight can get lost with

external help, context matters when solving problems. He recommends

following this flow of operations as you build out an internal CX team:


Export Your Early Work

While an internal CX unit is ideal if cost and structure in the early

stages don’t permit it: Find a freelancer who’s willing to commit to

longer-term, in-depth efforts, rather than contracting the cheapest-rated

personnel you can find. An added bonus is if they believe in the company

mission, rather than thinking about customer efforts as completing

tasks.


Bring on a Part-Time Generalist

As workloads scale with the company, Eli advises bringing on a generalist —

likely part-time and new to the workforce or trying to get their start in

your industry — in order to take on actionable (but time-consuming) tasks

across support tickets, operations, marketing, etc. Whether it be you

teaching them the basics or their natural ability, being able to give

beginner-level reports will make life that much easier.


Aside from gaining an extra set of hands across teams, this will teach the

cross-effects between various cogs of the company that ultimately make up

the end-to-end customer experience.


Hire a Full-Time CX Position

Once your brand has the capability, you can convert a part-time role into a

full-time one to maintain that consistency of company knowledge, or bring on

a fresh hire entirely.




Creating the Bridge Between CX and Retention

In Eli’s experience, CX and retention have often been approached as highly

segmented focus areas (i.e. paid acquisition versus organic growth versus

other buckets).


Yet, in reality, the problem of preventing customer churn can typically be

answered by deep familiarity with the actual customer experience.


As such, Eli recommends merging the two focuses by either:

  • Having one person handle both CX and retention — similar to the OLIPOP structure

  • Having the two teams function interdependently and but accountable to one another

“If you silo them, the retention team wonders how to win back users. And CX sits there with all the answers, because they’ve observed opinions on shipping times, return policies, and everything else that affects customer satisfaction.”



Good to Great: How Data Can Boost Your Existing CX

When it comes to designing for exceptional CX, Eli considers answering

support tickets to only be the tip of the iceberg.


Meanwhile, harnessing data insights, both qualitative and quantitative, to

continually improve the customer journey is the true core of an efficient

engine.


As he tells it, that could be as simple as ensuring the data points on your

website, i.e. discount rates and fulfillment times, are not setting you up

to fail. One of the biggest red flags of a potential customer is not

delivering on expectations, and they will always associate that with the

brand.


This is a straightforward way to either fumble or drive your LTV — and even

more of a reason to, again, keep CX efforts internal to maintain deeper

access to all elements of the user journey.


In terms of specific tooling, his team at OLIPOP primarily utilized Source Medium

to track performance metrics from end to end. This allows them to better

isolate what exactly drives an OLIPOP customer to return for more.


“Data can answer questions. But I find it’s more impactful when it proposes questions, like when I see a cohort of very sticky customers and get to investigate what we did correctly — maybe a certain campaign or promotion.”



The Dos & Don’ts for CX Performance Tracking

When Eli was at OLIPOP, these were his core KPIs:

LTV

OLIPOP can track LTV by segment, i.e. where customers come from, their

first-purchase characteristics, subscription vs. non-subscription, etc. LTV

also goes hand in hand with repeat purchases and subscriptions. Eli

describes a tool like Repeat

as crucial for nailing consumer timelines for CPG reorders and providing a

simple — and non-irritating — path for repeat purchasing.


NPS

The company also tracks NPS by factors like customer service scoring in

order to practically gauge CX efficiency and profitability. Other elements

include site quality, fulfillment speed and quality, and basic value prop.

There are also a lot of theories and numbers that can provide false signals.


And, here are Eli’s metrics to deprioritize:

AOV

In Eli’s words, AOV is overrated for gauging retention due to its

short-term frame for insight, hence his focus, from a CX perspective, on

LTV.


Margins

Beyond a fundamental healthy margin, agonizing over ratios of shipping to

unit pricing is also a short-term solution for CX and attempting to drive

repetition.




How to Leverage Metrics & Take Action

Rather than relying on costly methods such as paid ads, Eli recommends

leveraging your most loyal consumers for acquisition. For instance, he’d

segment buyers who’ve purchased OLIPOP 10+ times and offer discount codes

for free cases which they could share with friends.


Even more so, he believes the OLIPOP user can explain the product, and thus

evangelize, far better than he could, simply because the buyer can actually

communicate the experience of purchasing and truly loving the drink.

User-generated Content (UGC) from your biggest fans goes further than you

think when connecting with your next new customer.


Double Down on High-Repeat & High-LTV Buyers

In a similar vein, the OLIPOP team abides by the rule of thumb that once a

customer hits the benchmark of placing three single orders, they’re more

likely to convert to a long-term buyer.


Meanwhile, the opposite indicates their first or second-order will likely

be their last.


Another insightful metric Eli finds most brands don’t test for: Users

who’ve purchased OLIPOP 1–2 times in single orders before they subscribe are

ten times more likely to be retained than subscribers who sign up right off

the bat.


Steer Clear of Relying Too Heavily on Discounts

By successfully driving conversions through email, SMS, and similar

channels, the OLIPOP team has been able to steer clear of repeated

discounting. It’s a standard eCom tactic for retention — but one Eli advises

any brand with a high-value CPG to avoid.


For instance, many DTC brands will attempt to retain a user who’s been

absent for some time by sending them a noteworthy discount.


But with a soda product like OLIPOP, that’s priced at $2.49 (compared to a

75-cent Coke), a shopper will likely assume a marked-down can of OLIPOP is

more reflective of its true value than the original pricing — implying your

brand is marking up low-quality products for a profit. The result is not

only a devalue of the brand, but the team going down a misguided growth

path.


“We’re doubling down on the channels we own, like email and SMS, because no one wants to rely on Facebook every time they need purchases. Can we drive 30% of our revenue from our listservs? If we can, we’re in a terrific place.”

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Copyright © 2025 Skio. All rights reserved.

Grow your business with the most powerful all-in-one subscription suite on the market.


Copyright © 2025 Skio. All rights reserved.