Building Retention that lasts: reshaping Yotpo’s future, with Eli Weiss

The title is unusual, and that is intentional. When I first spoke with Tomer, Yotpo’s CEO, I was clear that I was not interested in SaaS. I had built my career working directly with brands, focusing on customer experience and retention, but I had never worked for a software company. My focus had always been on building relationships with customers and improving their experiences, not selling tools. But Tomer saw something in me. He told me, “You are an entrepreneur without risk tolerance.” He was completely right. I love launching things, fixing broken systems, and creating value, but I also like having stability.

At the time, I was at a crossroads. I could have started an agency and taken on multiple brands as a fractional leader, or I could have gone all in on my newsletter, which was already generating significant revenue. I had brands reaching out to me for consulting, and I could have structured it as a business. The model made sense. Many companies do not need a full-time retention or customer experience leader, but they do need strategic guidance for a few hours each week. If I took on a few clients, I could have made a lot of money while working very few hours.

I talked to agency founders who had built similar models, and they all said the same thing. “You are just accelerating the same problem. You will not be bored doing this for one company, you will be bored doing it for six.” That hit home. I did not want to do the same work over and over. I wanted something that felt new, where I could stretch myself in different ways.

That is when Tomer made me an offer that was different from everything else I had considered. He did not pitch me on a standard leadership role. Instead, he said, “Come in, meet as many people as possible, and find the biggest problems. If you hate it, you can leave after six weeks, and no one will even know you were here.” That was compelling. He was not trying to sell me on a position. He was giving me a challenge.

When I started meeting with the team, I realized something important. Externally, Yotpo had a reputation for being aggressive and transactional. But inside, the culture was the opposite. The team was full of high-EQ, thoughtful people who cared about brands. That disconnect was a massive opportunity.

At Yotpo, my role is not just about retention in the traditional sense. It is about making sure the company is deeply connected to the market. My job is to challenge assumptions, push for transparency, and help reshape how we engage with brands. On any given week, I spend time in multiple departments: Marketing, Brand, CS, and more. 

My entry into customer experience was with a luggage startup that had launched on Kickstarter. It was a great product, but we had a big problem. The company was massively delayed on delivering orders. Customers were frustrated, and my job was to handle support.

At first, I thought the role would be simple, but it quickly became clear that the situation was intense. People had spent hundreds of dollars on pre orders, and delays kept piling up. We did not have easy answers. There was no script that would make someone feel better about waiting months for something they had already paid for. I realized that the only way to turn the situation around was to change how we communicated.

Instead of just sending templated responses, I started being radically transparent. I told people exactly what was happening, why things were delayed, and what we were doing to fix it. I took full accountability, even when there was no perfect solution. Customers responded to that. Instead of anger, we got understanding. Instead of refund requests, we built loyalty.

That experience shaped everything I believe about customer retention. Most brands think about it in terms of discounts, loyalty programs, and automated flows. But real retention happens when customers feel like they are dealing with real people who actually care. That mindset carried over to every role I have had since.

I never set out to build a personal brand. I started tweeting about customer experience and retention because I was in the middle of it every day and wanted to share what I was learning. At Olipop, I was leading customer experience, constantly testing new ideas, figuring out what worked, and refining our approach. Twitter became the place where I documented those lessons.

I did not expect it to take off, but people paid attention. It went very slowly at first, and then really took off. In 2020, I had about 1,000 followers, but almost all were in DTC and high-value. I was the only one talking about topics like CX and Retention in a sea of growth guys.

Founders, marketers, and investors started engaging with my posts. When I launched my newsletter, I did not need to chase sponsors. They came to me because I was writing about topics no one else was covering in a real, unfiltered way.

That visibility opened doors. By the time I moved from Olipop to Jones Road Beauty, I was already connected to a network of people who cared about retention and advocacy. And when it came time to make my next move, I was not sending out applications. People already knew my work and were reaching out with opportunities.

Yotpo had actually sponsored my newsletter before I joined, and I had been aware of the company for years. After talking to Tomer and meeting the team, I realized this was not just another SaaS company. It was a place where I could actually make an impact, and impact is what I have always been searching for

At Yotpo, my focus is not just on keeping customers happy. It is on making sure we are listening, evolving, and building long-term relationships. The goal is to move away from the transactional mindset and towards something that brands actually trust. We want to play a long-term game in a short-term space.

That was not a sudden decision but something that had been building for a while. Yotpo has been around for more than a decade, and over time, like many SaaS companies, it became known for being aggressive in sales and pricing. But when I joined and started talking to the team, I saw something very different. Internally, the company is full of smart, empathetic people who genuinely want to help brands grow. The problem was that this reality was not reflected in how the market saw Yotpo.

Tomer, our CEO, had already started pushing for a shift before I arrived. He wanted to move away from the short-term, high pressure sales model that SaaS is often associated with and focus on building real relationships with brands. That meant taking a long term approach, even if it meant leaving some money on the table in the short term. When I came in, my role was to help connect the dots—how do we take this internal culture and make sure the market sees it?

One of the biggest areas we tackled was transparency. In the past, like many SaaS companies, pricing was often unclear, and brands felt like they had to negotiate their way to a fair deal. We are changing that. We want brands to feel like they know exactly what they are getting and that Yotpo is a partner, not just a vendor.

Another major shift was in how we engage with the brand community. Yotpo historically operated like a traditional SaaS company, focused on software and renewals. Now, we are putting real effort into being part of the ecosystem, hosting events that are actually useful, and creating spaces where marketers and founders can connect without feeling like they are being sold to.

It is a mix of strategic decisions and cultural shifts. One of the biggest changes is in how we approach deals. In the past, there was a mindset of winning every deal, no matter what. But sometimes, the best decision is to walk away. If we know that we cannot fully support a brand’s needs without messing with our roadmap or stretching in ways that would not positively impact the rest of our customers, we are not going to force a deal just to hit a number. That is a huge change.

Another example is how we engage with the community. One of the first things I worked on was Retention Uncensored, a series of events that strip away the typical conference fluff and get real operators in the room to talk about what actually works. No CMOs giving vague keynotes, no high level strategy decks—just people doing the work, sharing insights with each other. The first event in New York was a huge success, and we have since expanded to London and LA.

We are also focusing on education. A lot of retention and loyalty programs fail because brands do not know how to execute them properly. Instead of just selling a tool, we want to provide the knowledge and frameworks that brands need to be successful. That means more content, more hands on support, and more real conversations with our customers.

The goal is simple: Yotpo should be a company that brands want to work with, not because they have to, but because they see us as a valuable partner in their growth. That is what we are working toward.

Yotpo 2.0 is about shifting from a short term mindset to long term strategic growth. In the past, like many SaaS companies, Yotpo focused on closing deals aggressively, sometimes even when the product was not a perfect fit without making big strides to make it work. Now, we are taking a different approach. If we know we cannot fully support a customer, we are not going to force a deal just to hit a number. That is a huge shift in how we operate.

This also applies to how we position our email product. A year and a half ago, we would have tried to sell it to a big enterprise customer, even if we knew we did not have all the necessary integrations or support capabilities yet, and build as we go. Now, we are honest about what we can and cannot do. We do not want to overpromise and end up disappointing customers. That approach might mean saying no to revenue in the short term, but it builds trust in the long run.

Yotpo has multiple products including Reviews, Loyalty, SMS, and Email. Historically, these were treated as separate business units, but what we have learned is that the real value is in how they work together. A loyalty program is much more effective when it is integrated with SMS and Email, allowing brands to trigger personalized communication based on customer behavior. Reviews can feed directly into email campaigns, helping brands showcase social proof at the right moment.

The way brands buy these products has also changed. It is usually one or two decision makers, like the VP of Ecommerce, rather than separate buyers for each tool. That means they are looking for a platform that works seamlessly rather than piecing together disconnected tools. Our goal is to provide that without forcing brands into an all or nothing approach.

While lots of brands want consolidation, they also want best in class products. Nobody is going to use a weaker email platform just because it is bundled with other tools. We have to ensure that each product, whether it is SMS, Loyalty, or Reviews, is strong enough to stand on its own while also delivering extra value when used together.

There is also the question of flexibility. Some brands might already have an email provider they love but need better loyalty tools. We are making sure they can adopt what they need without feeling locked into an entire ecosystem. The value of Yotpo is in the synergy between products, but that does not mean forcing customers to switch everything at once.

Sales teams can sell across all products, but they rely on specialized engineers for deep technical questions. Someone selling SMS and Email does not need to know every small detail about the API integrations. That is where our solutions engineers step in.

Support is different. If a brand is using multiple Yotpo products, they need customer success managers who truly understand the tools. We have started hiring people from the brand side, former ecommerce operators, so they can bring real experience into customer conversations. If you are running a loyalty program, you want to talk to someone who has actually managed one before, not just a generic account manager.

That is a big part of my role at Yotpo. I help bring in people who have worked on the brand side, who know what it is like to run retention programs, and who can give brands the right guidance on SMS and email. It is not just about selling software. It is about making sure brands actually succeed with it.

Every career move has been driven by the need for growth and a new challenge. When things start feeling predictable and lack of challenge in the right areas, it is a signal to explore what comes next.

At Olipop, the focus was on building a strong customer experience function while working closely with email and SMS marketing teams. Moving to Jones Road Beauty meant taking on a broader retention role, which introduced a steep learning curve. The strategic side came naturally, but the data and analytics piece required stepping up in a big way.

After nearly two years at Jones Road, it became clear that while the business was booming,  I did not feel like I was impactful enough, and I wanted to be challenged in other ways. Financially, given the newsletter success, there was no longer a need to stay just for the paycheck, which raised a bigger question—what would be truly fulfilling? That moment led to a crossroads: go independent, start an agency, or take on a new challenge entirely. The decision to join Yotpo was about stepping into an entirely different kind of role, one that would push into new territory rather than repeating past experiences.

Most of my “friends” thought it was an outrageous move, and frankly, it looked wild on paper. I trusted my gut on the move, and I think most folks following my career now see what I did.

Staying engaged comes from being surrounded by people who are far more knowledgeable in certain areas. At Yotpo, the teams working on product, engineering, and analytics are operating at a level that demands constant learning. Being in rooms where others have deep expertise in fields outside of retention forces growth in new ways.

Career development has never been about perfecting a single skill set. The most interesting challenges come from jumping between problems, figuring things out quickly, and adapting to new spaces. The difficult part is sticking with a problem long enough to see it through rather than moving on too soon. That is where real growth happens.

Writing about customer experience and retention was never a deliberate attempt to build a personal brand. The newsletter started as a way to document what was happening day to day, turning real work into structured insights.

The wildest part is that in 2021, I had 3k followers, and in that span of 2 years I grew to over 20k. No growth hacks, no AI groups, no wizards commenting on my posts for pay or bots retweeting. Just me, sharing valuable insights and being 120% myself. 

Because there was already an audience on Twitter that cared about these topics, the newsletter gained traction quickly. Sponsors reached out on their own, largely because the content was grounded in actual experience rather than theory. Within a short period, it was generating almost as much revenue as a full-time role.

That shift changed everything. With financial security no longer a concern, the question was no longer about making more money but about finding the next challenge that would feel meaningful.

Always look for the side door.

I have never had a conventional resume. I did not go to college, and my early resume was just four lines long. If I had applied for jobs the traditional way, I would have been rejected every time.

Instead, every opportunity I have had has come through relationships, networking, and proving my value in non-traditional ways. That is something I always tell people—do not just rely on job applications. Find ways to connect with people, add value, and get your foot in the door however you can​.

I was recently gifted The Five Types of Wealth by Sahil Bloom, and it is on my list. The other book I love is The Psychology of Money by Morgan Housel​ and The Subtle Art of Not Giving a Fuck by Mark Manson. 

For podcasts, I listen to The Operators Podcast, which is run by ecommerce founders and good friends of mine who have built phenomenal businesses. I also love “How I Built This” and indulge in an episode of “Acquired” every now and then.