Raina Moskowitz is the CEO of The Knot Worldwide, one of the largest and best-known companies in the wedding industry, a role she took on in 2025. She previously served as Chief Operating Officer and Chief Marketing Officer of Etsy, and before that spent roughly 13 years at American Express. Raina joins Adam to share her journey and her best lessons and advice. Raina and Adam discuss a wide range of topics: leadership, team-building, career success, communication, community, trust, and much more.
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Read the full transcript of Adam’s conversation with Raina Moskowitz.
Episode Summary
Raina Moskowitz became CEO of The Knot Worldwide in 2025 after serving as Chief Operating Officer and Chief Marketing Officer of Etsy and spending roughly 13 years in a range of roles at American Express. In this Thirty Minute Mentors episode, she joins Adam to trace how a childhood built around community and team, from cheerleading in Cooper City, Florida, to a family culture of service, shaped a leadership philosophy centered on intentional connection, communication, and trust, especially in a globally distributed, largely hybrid organization.
Moskowitz credits her long run at American Express with two lasting lessons: the value of moving through eight or nine different roles across strategy, sales, marketing, and customer service, which built empathy and a holistic view of the business, and the company’s deliberate investment in leadership development beyond technical skill. She frames career growth less as a ladder and more as a series of intentional moves, crediting a mentor’s recurring question, “what job do you want two jobs from now,” as the framework she still uses in her own team’s career conversations today.
Now leading a company with employees across 11 countries, Moskowitz treats connection as something that has to be engineered rather than left to chance. The Knot Worldwide has a dedicated culture and experience team that plans and measures “intentional gatherings,” treating team connection with the same rigor as any other business initiative, tracked and reported rather than assumed to happen organically.
Communication is the skill Moskowitz returns to most, describing how her early career work behind the scenes, writing talking points and building decks for other leaders, taught her to watch closely how the best communicators operated before she had to do it herself. Her core practice now is framing every interaction, big or small, around a clear “why,” what the team is solving for, and how it connects to the company’s broader mission.
On leading hybrid and remote meetings specifically, Moskowitz describes a specific, granular practice: watching for people who unmute and then hesitate, and deliberately calling on them to make sure remote voices aren’t crowded out by people physically in the room. She frames this as part of a broader leadership responsibility not to dominate airtime, arguing that a meeting without real debate “probably could have been an email.”
Asked how leaders build trust, Moskowitz describes a combination of personal accessibility, being reachable and transparent even as CEO, and consistent follow through on what she hears in recurring roundtables with employees at every level. She’s explicit that trust isn’t built in a handful of big moments but compounds through many small, consistent actions, and that failing to follow up on feedback erodes credibility quickly.
On what she looks for when hiring, Moskowitz prioritizes people who are motivated by the mission and genuinely excited about the work over pure technical expertise alone, arguing that enthusiasm can’t be faked sustainably the way competence sometimes can be faked in the short term.
She closes on a theme less common in executive interviews: the discipline of protecting her own time for exercise, family, and sleep, treating self care as a leadership requirement rather than a luxury, on the logic that unprotected time will always be filled by work, and that a depleted leader can’t show up at their best for a team that needs them to.
What You’ll Learn
- Connection has to be engineered, not assumed. The Knot Worldwide runs a dedicated team that plans and measures “intentional gatherings” with the same rigor as any other business initiative.
- Ask “what job do you want two jobs from now.” The career development question Moskowitz’s own mentor asked her, and one she now asks her team in every career conversation.
- Watch for the unmute that doesn’t happen. Her specific technique for pulling remote voices into hybrid meetings: watching for people who almost speak up and deliberately calling on them.
- A meeting without debate “could have been an email.” Moskowitz’s litmus test for whether a meeting is actually worth holding.
- Trust compounds in small moments, not big ones. She credits consistent follow-through on feedback from recurring employee roundtables, not major announcements, with building real trust.
- Hire for hunger over pure expertise. Moskowitz prioritizes people who are genuinely motivated by the mission, arguing sustained enthusiasm can’t be faked the way short-term competence can.
- Protect your own time first. Exercise, family, and sleep are treated as a leadership requirement, not a luxury, since unclaimed time on the calendar always gets filled with work.
About Raina Moskowitz
Raina Moskowitz is the CEO of The Knot Worldwide, one of the largest and best-known companies in the wedding industry, a role she took on in 2025. She previously served as Chief Operating Officer and Chief Marketing Officer of Etsy, and spent approximately 13 years at American Express in a range of roles spanning strategy, sales, marketing, and customer service. She is a graduate of the University of Pennsylvania.
Related Episodes
- Episode 8: Doug Conant, Former CEO of Campbell Soup
A direct parallel on trust and leadership: Conant’s framework of character, competence, and walking the walk before asking a team to follow mirrors Moskowitz’s own account of trust compounding through consistent, small actions. - Episode 252: Terrance Williams, CEO of TruStage
Another CEO of a large organization on the deliberate work of building winning culture, a real-world counterpart to Moskowitz’s account of engineering intentional connection across a globally distributed team. - Episode 261: Liberty Mutual CEO Tim Sweeney
Discusses tone at the top, cultural cascading, and hiring for cultural fit at scale, themes that connect directly to Moskowitz’s approach to building her executive team as a “first team” united around shared values. - Episode 181: Wes Schroll, Founder and CEO of Fetch
Makes the same case Moskowitz does about transparency: that leaders who are honest with teams about both good and bad news build more durable trust than those who try to shoulder everything alone. - Episode 242: Principal CEO Dan Houston
A Fortune 500 CEO on leadership, teamwork, trust, and career development at a large organization, a useful complement to Moskowitz’s account of building trust and career mobility inside The Knot Worldwide.
