Leading Through Ambiguity: Building Teams and Careers That Thrive: Jordan Schwartz

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This episode of The Eh List features a thoughtful conversation with strategy leader Jordan Schwartz, who shares how leadership, growth, and human connection shape successful organizations. With more than a decade of experience at the intersection of technology and business, Jordan reflects on his journey from university to his current leadership role at Caylent, explaining why following instinct and staying open to opportunity can be more valuable than rigid career planning.

Jordan discusses the importance of building strong relationships, investing in personal development, and creating cultures that support long-term growth, especially in fast-changing business environments. He also highlights why hiring for cultural fit matters and how leaders can balance strategy with execution when expectations are high.

Drawing from his early career experiences, including his time at Traction on Demand and its acquisition by Salesforce, Jordan explains how an exploratory approach helped shape his path. He introduces the idea of delayed gratification, encouraging young professionals to focus on long-term development rather than short-term rewards.

Throughout the episode, Jordan emphasizes the role of company culture, the value of meaningful connections, and the impact of finding leaders who challenge you to grow. He reminds listeners that every organization has its own subcultures, and understanding them can play a major role in career success.

Overall, Jordan’s story is a reminder that careers are rarely linear. Success is driven not by job titles or company names, but by the experiences you gain, the relationships you build, and your willingness to adapt as opportunities arise.

Companies mentioned in this episode:
Traction on Demand
Salesforce
Caylent
Live Different

Books mentioned in this episode:
Good to Great by Jim Collins

Check out Jordan Schwartz's socials below:
  / jordanschwartz1