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Introduce yourself! Who are you and what do you do?

I’m Melissa Gilbo and before anything else, I’m a mom, wife, sister, daughter, and friend. Those roles come first. They keep me grounded and remind me that leadership starts at home. I’m a proud boy mom from a small Massachusetts town who still believes kindness and consistency win every time.

Professionally, I’m the Founder and CEO of Women’s Business League, a national community for women in business. But it didn’t start that way. It started at my kitchen table with a laptop, a big idea, and probably a cold cup of coffee I never got to finish.

I built WBL while working full time in the insurance industry. So yes, I was selling policies by day and building a movement by night. Early mornings, late nights, squeezing in calls between client meetings and sports practices. It was messy, real, and fueled by belief more than a business plan.

There was no investor backing me. No fancy launch strategy. Just a deep conviction that women deserved better rooms. Rooms that felt collaborative instead of competitive. Rooms where you didn’t have to perform, posture, or pretend. Just show up as you are and build something meaningful.

Today WBL is a thriving national network focused on connection, visibility, leadership development, and real growth. But at the core of it all, I’m still that small town girl who believes relationships change everything and that showing up consistently matters more than being the loudest in the room.

And we are just getting started.

What made you want to start your business?

Honestly, I started Women’s Business League because I couldn’t find what I was looking for.

I was attending networking events that felt transactional and surface level. Everyone was handing out business cards, but no one was really building relationships. I remember thinking, there has to be a better way to do this.

I didn’t want another room full of elevator pitches. I wanted real conversation. Real collaboration. Real support. I wanted women to walk into a room and feel like they belonged, not like they had to prove something.

At the same time, I was growing in my own career in insurance and learning firsthand how powerful relationships are in business. Every opportunity I had came through connection. So I started wondering what would happen if we built something intentionally around that idea.

So I gathered a few women. No big announcement. No five year plan. Just let’s try this and see what happens.

What happened was momentum.

Women were craving it. They were craving depth. They were craving support without ego. They were craving community that didn’t feel like competition.

Starting WBL wasn’t some perfectly mapped out entrepreneurial leap. It was more of a “this feels needed, so I’m going to build it” moment. And then continuing to say yes long after it got hard.

Now I get to wake up every day and build rooms that create opportunity for other women. And that is worth every late night, every doubt, and every cold cup of coffee along the way.

What do you love the most about owning a business in Massachusetts?

I’m a North Shore girl and actually I’ve never lived anywhere else. This is home home. The ocean air, the town pride, the Friday night lights, the Boston accents, the layered up winters and the blink and you’ll miss it summers. It’s in my DNA.

What I love most about building a business in Massachusetts is the character of the people. There’s honesty here. There’s loyalty here. You say you’re going to do something, you do it. Relationships matter. Reputation matters. And if you show up consistently, people remember.

Massachusetts is also competitive in the best way. We love our sports, we love to win, and we love to work hard. That energy carries into business. There’s grit. There’s resilience. There’s innovation. You’re surrounded by smart, driven people who push you to elevate your game.

And let’s be honest, surviving four seasons builds something in you. We can handle a snowstorm in February and still show up to a morning meeting. We know how to pivot. We know how to adapt. That mindset absolutely shapes how we build businesses here.

For me, growing Women’s Business League in the state I’ve always called home feels deeply aligned. I understand the heartbeat of these communities because I am one of them. And I’m proud that what started on the North Shore is now expanding far beyond it, while still carrying that Massachusetts grit and heart with it.

What are your favorite small businesses to support in Massachusetts?

This one is almost impossible for me to answer because there are so many. Truly. If I started naming names I’d leave someone out and that would bother me all day.

My heart is with the small business owners who are in it every single day. The ones opening the doors before sunrise. The ones doing payroll at their kitchen table. The ones wondering if this month will cover the bills. The ones who don’t have big marketing budgets but still show up with big heart.

I love the local coffee shops, boutiques, salons, photographers, fitness studios, consultants, family owned restaurants, all of it. Not just because of what they sell, but because of the courage it takes to build something from scratch.

Small businesses are the heartbeat of Massachusetts towns. They sponsor the little league teams. They donate gift cards to raffles. They know your name when you walk in. That matters.

So honestly, my favorite small businesses to support are the ones brave enough to try. The ones building quietly. The ones who need visibility and community as much as revenue.

If you’re a small business owner in Massachusetts, I am 100% rooting for you.

What has been the biggest lesson you’ve learned throughout your career?

The biggest lesson I’ve learned is that consistency beats intensity every single time.

You don’t need one viral moment. You don’t need the perfect plan. You don’t need to feel fully ready. You need to keep showing up.

I built Women’s Business League in the margins of my life while working full time and raising my boys. There were seasons where it felt so hard and heavy. There were seasons where I questioned myself. But I kept showing up. I kept hosting the events. I kept making the calls. I kept believing in the vision even when it didn’t know if it would all work out.

Another big lesson? Relationships are everything. Every major opportunity in my career came through connection. Not cold pitches. Not fancy marketing. Real relationships built over time.

And maybe the most personal lesson has been this: you can grow without changing who you are. As the vision expanded, I had to expand too. But I didn’t have to become someone else. I had to become more anchored in my values, not my ego.

Consistency. Relationships. Values.

That’s the formula I’ve learned to trust.

If you weren’t in your current position, what would your next dream job be?

I would own and manage a lakeside family resort. No question.

I picture living right on the property. Morning coffee overlooking the water. Kids running around barefoot. Families coming back year after year asking for the same cabin because that’s where their traditions started.

I love the idea of building a place where community is baked in. Bonfires at night. Paddle boards during the day. Lawn games. Ice cream by the dock. A space where phones are down and memories are being made in real time.

It probably makes sense when you think about it. I build community now, just in a different setting. At my core, I love bringing people together. I love creating environments where connection happens naturally.

A lakeside resort would just be another version of that. A place where making memories and having fun is the priority. Where families leave a little more connected than when they arrived.

And honestly, I don’t hate the idea of trading event heels for flip flops someday.

When you’re not working, what activities do you enjoy?

If it’s summer, you’ll find me outside. I love being on a lake with my family and friends. Boating, swimming, sitting on the beach doing absolutely nothing, which is rare for me. There’s something about water that slows me down in the best way.

Nights are for campfires. Good music. Barefoot kids. Long conversations that somehow feel deeper under the stars. That’s my reset.

I’m also mildly obsessed with my dog. He thinks he runs the house and honestly… he might. Walks, snuggles, talking to him like he fully understands business strategy. It’s fine.

And country music? Always. Windows down, volume up, whether I can sing or not is irrelevant.

When I think about my dream of owning a lakeside family resort someday, it makes sense. The things I love most all center around being outside, being together, and creating memories that stick.

Work is important to me. But so is building a life that feels full. Summer nights, lake days, my people, and good music. That’s the good stuff.

Thank you for sharing more about yourself! Tell us how we can get in touch with you or find you online.

You can learn more about me via my website, Instagram, and LinkedIn.