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, the CEO of The Knot Worldwide since 2025, spent roughly 13 years at American Express before becoming COO and CMO of Etsy. She credits her time at Amex with two specific lessons rather than a general sense of loyalty: the company moved her through eight or nine different roles across strategy, sales, marketing, and customer service, and it invested deliberately in leadership training on top of technical skill. A mentor there gave her a question she still asks her own team in every career conversation: what job do you want two jobs from now.
Now leading a company spread across 11 countries, Raina treats team connection as something that has to be built on purpose rather than left to chance. The Knot Worldwide runs a dedicated culture and experience team that plans and measures what it calls intentional gatherings, tracking them with the same rigor as any other business initiative. In hybrid meetings specifically, she watches for a very specific cue, someone who unmutes and then hesitates, and deliberately calls on them so remote voices aren’t crowded out by people in the room. Her test for whether a meeting was worth holding at all is blunt: if there wasn’t real debate, it probably could have been an email.
Raina describes trust as something that compounds in small, repeated actions rather than a handful of big moments. She points to her own habit of running recurring roundtables with employees at every level, taking notes, and following up visibly on one or two themes each time, arguing that failing to follow through on feedback erodes credibility fast. When hiring, she looks past pure technical expertise for people who are genuinely hungry for the mission, since she has found that hiring the most technically skilled candidate is not always the right call.
Raina also frames her own executive team as what she calls her first team. When she hired her current CFO, she told him directly that she didn’t need a head of finance, she needed a member of her executive team willing to show up united with the rest of the group. She closes by describing a habit she treats as a leadership requirement rather than a luxury: blocking calendar time for exercise, family, and sleep, on the premise that any unclaimed time on a leader’s calendar gets filled with work by default.
What You’ll Learn
- Communication improves with practice: Raina spent years writing talking points and decks behind the scenes, including in a chief of staff role, and she says anyone can practice by framing every meeting around what the team is solving for.
- Seek champions as well as mentors: Raina distinguishes mentors, who advise you, from champions, who look out for you and put you forward when opportunities arise.
- Build trust by following through: Raina takes notes at her employee roundtables and acts quickly on one or two themes from each, and her company reports back on its employee survey, including where it can do better.
- Help people grow across functions: Raina asks team members what job they want two jobs from now, then looks for moves and projects that build the skills to get them there.
- Treat your executive team as your first team: when Raina hired her CFO, she told him she did not need a head of finance, she needed a member of her executive team.
- Be less scripted and more accessible, Raina says, because letting your team know you as a human as well as a leader builds trust, especially when so much work is virtual.
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 roughly 13 years at American Express across a range of roles spanning strategy, sales, marketing, and customer service. Raina grew up in Cooper City, Florida, where she cheerleaded through high school and continued cheerleading at the University of Pennsylvania, crediting that early experience with an enduring focus on team and community that carries into how she leads today.
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