Eli Weiss: Branding, Burnout, and Breaking the Rules | Subscription Heroes #23

Eli Weiss has led customer experience at brands across wildly different industries. He’s worked with better-for-you consumer companies like Olipop and Jones Road Beauty, and now he’s VP of Retention Advocacy in the SaaS world at Yotpo.

During our conversation, we were surprised to learn that Eli has never gotten a job through HR. Every opportunity he’s had came through real, human connection. At one point, he even got hired by someone he casually interacted with on Twitter. That emphasis on connection shows up everywhere in his career. Which also shows that human connection isn’t just meaningful, but it’s magically transformational too.

We sat down with Eli to talk about building a nontraditional career, why emotional intelligence matters more than ever, and what led him to leave high-growth DTC roles in search of work that felt more meaningful and expansive.

If you're building your first team, stuck between two job offers, or just thinking hard about how work should feel—this one’s for you.

Your Career Doesn’t Have to Look Like Anyone Else’s

Eli’s career looks more like a jungle gym than a ladder, and he’ll be the first to say it: careers aren’t always linear. He’s moved across function—customer experience, retention, brand—and he’s jumped between industries, with some roles lasting years and others just a few weeks. Still, each move was intentional, guided by gut instinct for when it was time to grow.

His advice to early-career operators is simple: go for signal. Take the job with the best brand, even if it pays a little less. And don’t forget to build credibility, because that’s what unlocks more doors down the line, often in ways you can’t predict yet.

Perfect job

For Eli, the dream job isn’t about chasing titles or maximizing pay—it’s about alignment, challenge, and fun. Once money stopped being a daily worry, he stopped optimizing for income and started optimizing for energy. He looks for roles that feel exciting to do, not just impressive on paper. To him, the perfect role is one that fits who you are right now, while also pushing you toward who you’re becoming. And today, that means optimizing for three things:

1. Fun – “A job shouldn't be fun, but I love having fun at my job. I love when it feels exciting, even if it's not 90% of the time.”
2. Challenge – “I want to be the dumbest person in the room.”
3. Real problems – “I want a really hard problem to solve.”

“The dream is finding a role that wants exactly who you are, plus 30% growth. That’s it.”

For early-stage SaaS founders: what can you learn from Eli?

If you’re building a team or thinking about your next hire, here are some takeaways to steal:

• Prioritize emotional intelligence. Most people don’t lose jobs because they’re bad at the work, but they lose them because they can’t communicate or work well with others. EQ matters more than most hiring processes reflect.
• Hire for culture fit, not just credentials. People thrive in environments that align with how they work best. If the culture’s off, even talented hires will underperform.
• Look beyond specialization. Eli made a career out of being a generalist. In early-stage teams, that kind of flexibility and range can be a strength—not a weakness.

And last but not least, trust yourself. You usually already know when something feels off—or when something feels right. The hard part is giving yourself permission to act on it.

Eli’s built his entire career by following that instinct. Not just chasing titles or paychecks, but choosing roles that feel aligned, challenging, and energizing.