I recently one-on-one with Melissa Krueger, CEO of Classic Vacations.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Melissa: I grew up in a small town in the Pacific Northwest, raised by first-generation American parents whose parents settled in the Dakotas, immigrating from Scandinavia, and instilled in me a deep work ethic and an appreciation for resilience. I’m the middle of three sisters, and with a wide age gap between us, I learned early on how to both lead and support, navigating different dynamics, reading the room, and understanding how to bring people together. Those early experiences shaped how I lead today: grounded in empathy, clarity, and an instinct for building trust – and that good hard days’ work is the cure for a bad day.
At 25, I didn’t even know the travel industry was an industry. I started working for a French-based hotel company with the vague idea that maybe it would one day take me to Paris. What I found instead was a career. I’ve since spent more than two decades in travel across sales, brand development, and strategy, but it wasn’t always linear or easy. Juggling career growth while raising a family demanded a level of agility and discipline I didn’t anticipate. I was fortunate to work under leaders who valued outcomes over rigidity and who gave me room to be nimble and approach things differently. That flexibility became one of my greatest assets.
Throughout my career, what’s driven me most is the relationship side of leadership: the chance to contribute to other people’s success. I’ve always believed that great leaders build great leaders. That philosophy led me to Classic Vacations more than a decade ago, where I gradually took on broader responsibilities before stepping into the CEO role. Leading this brand, protecting its legacy while also evolving it for the future, has been the most rewarding challenge of my career. It’s taught me that true leadership lives in the tension between tradition and reinvention.
Adam: In your experience, what are the key steps to growing and scaling your business?
Melissa: You can’t scale a business by preserving what was; you scale by building on what’s possible. When I stepped into leadership at Classic, I inherited a brand with legacy, but not momentum. That distinction matters. My focus wasn’t on protecting the past; it was on honoring what worked while reshaping the company for long-term, sustainable growth.
For me, everything starts with understanding what the customer needs and then making sure we’re aligned across the board: with our supply strategy, for our supplier partners, and through our people. It’s not about isolated wins; it’s about creating a business model where every advisor, supplier, and employee thrives.
Scaling requires urgency. Luxury doesn’t wait, and neither can we. There’s a discipline in being decisive, especially when the safer choice is to pause or wait something out. It’s not about rushing; it’s about refusing to stand still.
Adam: What do you believe are the defining qualities of an effective leader?
Melissa: I believe effective leadership is equal parts nurture and accountability. The best leaders care deeply about their people, but they also set high expectations and hold the line. You can’t claim to support someone if you’re not helping them stay accountable for their goals. That’s not just about performance; it’s about respect for their growth, their career, and the families they’re providing for.
One of the most defining qualities of a strong leader is the ability to have clear, direct conversations. Few people are truly comfortable doing that, but those who are build individuals and teams that are resilient and high performing.
A key part of leadership is knowing how your people operate. Some need you to outline the path, while others just need to understand the outcome you expect and will figure out how to get there. Good leaders don’t shy away from those assessments; they lean into them. They observe, listen, ask questions, and adjust their approach accordingly. It’s not one-size-fits-all; it’s intentional leadership.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Melissa: That’s a good one, because the truth is, leadership growth doesn’t happen in isolation. Surrounding yourself with strong, capable people is essential. If you don’t have the right team, you’ll spend your time doing your last best job instead of excelling in your current one, let alone having the space to think strategically and grow as a leader.
That said, leadership can feel isolating at times. The higher up you go, the fewer peers you have to process with. That’s why it’s even more important to stay grounded by staying connected, whether it’s through trusted colleagues, mentors, or simply being open to real conversations across all levels of your organization.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Melissa: Build the right team, then get out of their way. Whether you’re running a business, scaling a brand, or leading a community initiative, your ability to succeed depends on the strength of the people around you. In luxury, especially, excellence is non-negotiable. You need to surround yourself with smart, capable, value-driven people, and then trust them. Give them the clarity they need, and the space to deliver.
Be decisive and don’t wait for perfect. I see this often in leadership: we wait too long, tinker too much, or stall because something’s not quite “ready.” In luxury, speed and precision matter. Leaders need to be willing to make decisions with the best information they have and own the outcome. Momentum is a competitive advantage. You can’t lead if you’re always in draft mode – execute at 85%.
Stay connected to the people you serve. Whether it’s a client, a customer, or a community, never get so far removed from the day-to-day that you lose perspective. Make the calls. Walk the floor. Have the conversations. Leadership isn’t just strategy; it’s proximity. The best ideas, solutions, and relationships are built by staying close. Build for the next 50 years.
Adam: What is your best advice on building, leading, and managing teams?
Melissa: The best advice I can give on building, leading, and managing teams is to consistently show up with clarity, purpose, and a steady hand. Your team takes its cues from you, especially in uncertain moments. They need a leader who communicates expectations clearly, speaks in outcomes, and doesn’t avoid the hard conversations. If you can’t be direct, you’ll never build trust or results.
Reputation matters. Building a strong team is far easier when you’ve earned credibility, when people know you show up for others, contribute to their success, and deliver on what you promise. At the end of the day, your personal brand as a leader is built on how reliably you support other people’s businesses, careers, and lives.
I also believe in being intentional with culture. You are a team, not a family. Teams are held accountable. They’re aligned around shared goals, and they make hard decisions when performance or priorities demand it – and sometimes one part of the team carries the other.
Leading well isn’t about doing everything yourself. It’s about creating an environment where people know what’s expected, have the tools to succeed, and feel proud to be part of something that delivers excellence.
Adam: What are your best tips on the topics of sales, marketing, and branding?
Melissa: I love this topic because sales, marketing, and branding are at the heart of how any business grows, connects, and leads.
Sales: One of the best questions a salesperson can ask is: “What would it look like to you if I were the best sales rep you’ve ever worked with?” Very few ask that, but it’s one of the most powerful ways to cut through assumptions and get to the heart of what your customer actually needs. Sales isn’t about boilerplate pitches; it’s about listening, caring, and building real partnerships. I’ve built my entire career on that philosophy: genuinely investing in my customers’ success.
Marketing: By definition, marketing is about creating demand. But that only works if your organization is aligned behind the message. It’s not just what you say externally; it’s what the rest of the business is prepared to back up. I’m a firm believer in social proof. In a high-trust industry like luxury travel, showing that others have succeeded with you is far more powerful than telling people they should.
Brand: To me, the best definition of brand is simple: it’s the promise you make, and how consistently you deliver against that promise. Everything, from your service standards to your visual identity to how your team shows up, should reinforce that. In luxury, the margin for error is small, and consistency is everything.
Adam: What is the single best piece of advice you have ever received?
Melissa: The best leadership advice I’ve ever received came from my father: “Take what we did right and repeat it, but leave what we got wrong at the door when you go.” It was a reminder that honoring the past doesn’t mean replicating it. That insight has stayed with me throughout my career.
As leaders, we often inherit systems, strategies, and legacies, some strong and some outdated. The real challenge is knowing what to carry forward and what to release. Change can be uncomfortable, especially when it’s tied to something people built or believed in. But growth requires honest assessment, and strength lies in evolving with intention, not obligation.
The ability to move forward while still respecting what came before is what defines sustainable leadership. It’s how we build better, stronger organizations without being constrained by the way things have always been done.
Adam: Is there anything else you would like to share?
Melissa: Looking Ahead: Leadership isn’t just about driving results; it’s about building for the future. I believe we have a responsibility to share our journeys so that others can see what’s possible. No one becomes a leader in isolation. I’m committed to being accessible to the next generation—whether that’s through mentoring rising professionals, serving on industry and academic boards, or simply saying yes to a conversation with a student curious about our field.
The more open we are with our experiences – the wins, the challenges – the more we help clear a path for others to follow. And in doing so, we don’t just build stronger organizations, we build a stronger industry.
