How Traveling Shaped Eli Weiss's Career

In this episode, Eli Weiss reflects on his unconventional path from a financially unstable childhood and world travels to becoming a leading voice in CX and SaaS marketing at Yotpo. They explore Eli’s evolution from generalist to CX specialist, the emotional and strategic challenges of job-hopping, and how brand-building, EQ, and personal intuition shape modern careers. The conversation blends life philosophy with tactical advice on marketing, career development, and the tension between art and science in SaaS go-to-market efforts.

About Eli Weiss:

Eli Weiss is a customer experience and retention expert known for his work with leading DTC brands like Ollipop and Jones Road Beauty. He currently leads brand and marketing strategy at Yotpo, where he combines his CX background with go-to-market leadership. Eli is recognized for his transparent storytelling, strong focus on emotional intelligence, and unique ability to bridge customer insights with brand building in SaaS.

Here is what we cover:

● Early Background: Grew up with financial instability; developed a scrappy, entrepreneurial mindset.
● Travel & Perspective: Traveled globally using credit card points; shaped worldview and independence.
● CX Career: Worked across startups like Ollipop and Jones Road Beauty; scaled subscriptions and built retention strategies.
● Yotpo Transition: Joined Yotpo after a career reset, combining CX, brand, and strategy roles.
● Marketing Approach: Emphasizes ROI metrics (MQLs, pipeline), but values long-term brand building.
● Emotional Intelligence: Believes EQ drives career success more than IQ; critical for leadership.
● Career Philosophy: Trust intuition, take strategic bets, and seek roles that align with strengths.
● Generalist Insight: Generalists do well in startups, but face challenges in larger corporate structures.
● Brand Advocacy: Uses CX insights to inform go-to-market, ABM, and product strategy.
● Final Advice: Stay adaptable, trust your gut, and invest in personal growth in an AI-driven world.