Chief of staff insights and leadership lessons from Kaitlan Norrod at Replit

We recently sat down with Kaitlan Norrod, former EA and now chief of staff at Replit, as part of our blog series highlighting the best executive assistants in tech. These chief of staff insights offer a clear picture of how strategic support roles can transform executive effectiveness.

When you look at Kaitlan’s career, it’s clear she didn’t just step into operations leadership; she built toward it intentionally. Kaitlan focuses on operational clarity, executive enablement, and building systems that keep the company running smoothly. These chief of staff insights reveal what it really takes to help executives focus on what matters most.

Table of contents:

1. Can you tell us a little bit about your career and current role?
2. What would you say to an executive who thinks their company is too small to hire an EA?
3. Many executives hesitate to give their assistants access to their inbox. As the former EA to the CEO at Superhuman, how would you help them feel more comfortable delegating email?
4. Besides email, what are the top 5 things all executives should delegate?
5. What’s one thing you do that consistently makes your executives more productive?
6. What’s the impact of an EA beyond supporting an executive?
7. What’s one thing EAs can do that makes executives say, “Wow, I didn’t know you could do that”?
8. What is the secret to building a successful EA/executive relationship?
9. What’s the most difficult situation you’ve had to handle as an EA?
10. What is the smartest way you’ve used AI to support your executive?

1. Can you tell us a little bit about your career and current role?

I started my career as a personal assistant to Randi Zuckerberg, which quickly evolved into an executive assistant role as her business grew. From there, I joined Yelp, where I supported anywhere between three to seven SVPs as the company scaled from about 1,000 to 6,000 people. Eventually, I supported both the COO and CAO, who led legal, HR, and user operations.

I then moved to Superhuman as employee 17, supporting the CEO and helping build the company to over 120 people. I loved that growth stage: small enough to be scrappy but structured enough to see real impact. When a mentor at Replit mentioned they were hiring an EA for the leadership team, I joined as their 50th employee. I worked closely with the CEO, and over time, that partnership evolved into my current role as chief of staff, focused on operational clarity and executive enablement.

2. What would you say to an executive who thinks their company is too small to hire an EA?

It’s not about company size, it’s about workload. If you’re spending too much time on logistics instead of priorities, that’s when an EA makes sense. At Superhuman, our CEO was protective of his time, which was great, and having a partner focused on where that time was spent made all the difference. That’s what a great EA relationship can do: protect focus and drive alignment.

3. Many executives hesitate to give their assistants access to their inbox. As the former EA to the CEO at Superhuman, how would you help them feel more comfortable delegating email?

It takes time and trust. I always start by understanding how they use email: what’s working, what’s not, and where optimization can happen. The goal is to remove the friction that stops them from getting into their day. I learn their tone of voice, build filters, and start drafting emails on their behalf. Once they see that I can anticipate their needs, trust follows. Everyone uses email differently: some as a to-do list, others as triage, and tailoring support to that workflow is key.

4. Besides email, what are the top 5 things all executives should delegate?

• Definitely the calendar. It’s simple, but many leaders still hold on to it too long.
• Next is communication flow: following up on meetings or messages so nothing slips.
• Then, meeting prep: ensuring every session has the right context and materials.
• Relationship management is another, whether through a lightweight CRM or follow-up reminders.
• Finally, documentation. Once routines are documented, you can automate and optimize them, freeing the executive from repetitive work.

5. What’s one thing you do that consistently makes your executives more productive?

I keep them focused on their zone of genius. At Superhuman, that meant giving our CEO time to think about product and design: the areas where he created the most value. I also practice proactive alignment: noticing what’s happening in the business and helping refocus priorities when needed. Sometimes that means saying, “We planned this for the week, but this new development might need your attention.” It’s about anticipating shifts before they happen.

6. What’s the impact of an EA beyond supporting an executive?

Team enablement. A great EA doesn’t just make one leader more effective, they help the entire leadership team move faster. When executives get the answers they need sooner, they can work more closely with their teams and keep momentum across the company.

7. What’s one thing EAs can do that makes executives say, “Wow, I didn’t know you could do that”?

Forecasting. People joke that EAs can read minds, but it’s really about pattern recognition. You can see how decisions will ripple through the organization and flag issues before they surface. That kind of foresight changes how executives plan and respond; it’s almost a superpower.

8. What is the secret to building a successful EA/executive relationship?

Trust, built on honesty and openness. The best relationships I’ve had with executives are rooted in transparent conversations about what’s happening across the company and how we’re both feeling about it. Shared tools matter too: if your exec loves using a specific app, learn it and adapt your workflow so you can stay aligned. That’s how you start truly taking things off their plate.

9. What’s the most difficult situation you’ve had to handle as an EA?

One of my most challenging experiences was working with an executive whose style didn’t mesh with mine. I’d supported many people across the company and considered myself adaptable, but with this executive, even small things, like coordinating flights or communication, felt harder, and I questioned my effectiveness.

My executive and I had dinner to discuss our partnership and realized we had very different levels of context, each making assumptions based on what we knew. That insight led them to share more background with me, helping me make better decisions, learn their working style faster, and build deeper trust.

A recent example of a difficult situation was an internal event in Huntington Beach. Our CEO was invited to speak at the event the week prior and we wanted to make it work so we had to do some last minute shifts to the schedule to get him to the engagement while also not missing anything too important at the internal event. I had to quickly restructure the agenda so he could do both. Since it was domestic, it was manageable, but it reinforced how much adaptability and problem-solving matter in this role. In the end, everything worked, and it was a big learning experience about working effectively with different executive styles.

10. What’s the smartest way you’ve used AI to support your executive?

One of my favorite ways has been automating our CRM. For years, I’ve built CRMs for my executives using Airtable: tracking meetings, updating contacts, and setting reminders to follow up after 45 days. Traditionally, this was manual work, but with AI, I’ve automated most of it. Calendar data now flows in automatically, reminders are set, and I just clean up the details.

This automation removes a lot of administrative burden, so I don’t have to think about data entry anymore. I use Airtable, Replit, and Slack for reminders, though email can also work for quick overviews. Now, my executive can easily see who to follow up with in one-on-ones, making outreach and relationship management much smoother.

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These chief of staff insights make it clear: executive assistants are there to help you lead and find your zone of genius. Ready to experience the difference a great executive assistant can make? Book a call today, and we’ll match you with a Viva EA who creates space for focus, alignment, and strategic work.

Fadua Caicedo Díaz del Castillo

Fadua is a bilingual advertiser and holds a master’s degree in creative writing. With over ten years of experience, she has written countless advertising and social media campaigns, blogs, interviews, and everything in between. She writes about startups, the impact of executive assistants, and the stories behind their work. When she’s not writing, she is spending quality time with her husband and son, hiking, reading, or discovering new cafés.