Humble, Hungry, and Human: Building Teams with Rachel Grundy

Rachel Grundy didn’t plan to become a Chief of Staff, but somewhere between her days acting and playing music in NYC and her current role at ButcherBox, she’s built a beautiful and unexpected career story. Along the way, she’s learned the power of curiosity, humility, and a healthy ego and how those qualities shape the way she hires and leads.

In today’s newsletter, Rachel shares her top takeaways from that journey.

What are some key takeaways from any of your career transitions?

Stay open to unexpected opportunities.

Openness to what might be out there, even if it’s surprising, has been a huge part of my success.

You don’t always feel like you can control where you land as a job seeker, but if you know who you are and what you're looking for, whether it's culture, the team, or the type of role, and being flexible with the rest can help.

In addition to being open, focus on having a growth mindset. Embrace change, embrace challenges, and look to learn from every experience. Even when it’s hard, ask: “What can I learn from this?” or “How can I grow from this?”

What’s one quality you always look for in new team members to ensure they align with your team’s culture?

Humility. An A-Player will be a lifelong learner and will ask questions without ego. They’ll be open to giving and receiving feedback, which usually means they’re self-reflective and have good self-awareness.

That kind of attitude is foundational to a strong team culture because when the team is successful, the individuals will be too.

How do you evaluate whether someone will be a good fit for your team?

In interviews, I focus more on how someone shows up rather than their hard skills. Their resumes tell me enough about their skills, but in the interviews, I want to learn more about who this person is.

I look for a humble attitude and curiosity. The best team members are genuinely interested in their coworkers.

Low ego is good, but for me, it’s really about a healthy ego. Someone who wants to succeed and is hungry, but not at the expense of the team.

I also look for great communicators. People who can be authentic, give and receive feedback with kindness and empathy, and ideally…bring a sense of humor. You spend most of your time at work, so it should be fun.

If you participate in the hiring process, what’s a recent hire that went really well? What did you learn from the process?

We recently hired a product manager for a newly forming team, and I helped lead that process.

We were really clear from the start about both experience and the kind of person we wanted on the team. That clarity made everything easier.

We filtered resumes based on required experience, and then focused interviews on the intangible qualities: someone collaborative, team-oriented, a strong communicator, and someone who could shape a positive team environment.

We asked questions like: “Tell me about a time when a project didn’t go well. How did you handle it?” “How do you help your team celebrate success?”

That alignment and clarity helped us make a great hire.

What’s the biggest challenge you’ve faced in hiring or leading a team, and how did you overcome it?

When I first started building my team at ButcherBox, we needed help fast. I was supporting so many teams on my own.

We made great hires, but in retrospect, I learned the importance of not hiring reactively. Even when things feel urgent, you need a clear vision for both the current team and where it’s going.

That’s what helps you hire for long-term potential and create roles that offer growth paths. People want to see where they’re headed. And that matters for retention, too.

If you could give one piece of advice to job seekers, what would it be?

Stay true to who you are and be authentic in your job search. The market is hard right now, and it can feel like you have to mold yourself to fit. But being yourself is what actually makes you stand out.

Something I always look for is a cover letter that actually sounds like the person wrote it. I tell people to use their voice, speak from their authentic self. That doesn’t mean you’ll land every job, but it means the right opportunity will find you.

What’s one thing job seekers should know about interviewing with your company?

At ButcherBox, we care deeply about our culture and values: humility, authenticity, and accountability.

We’re hiring for excellence, but we also want people who care about the team and the bigger picture. When there’s alignment with our values, people feel like they belong, and that motivates them to show up as their best selves.

What’s one skill or trait you predict will be essential for success in the workforce moving forward?

Resilience. The world is changing so rapidly. People are overwhelmed and uncertain. And whether it’s your job search or life in general, we all hit hard times.

If you haven’t built the practices and habits that help you be resilient, it’s hard to move through those moments. But if you have, then when things get tough, you have something to fall back on and you’re able to stay open and keep moving forward.

Thanks so much for sharing, Rachel.

If you’d like to learn more about Rachel or her work at ButcherBox, check out her LinkedIn here or their website here.