What I Learned Acquiring 100 Dental Sites in One Year

When someone throws a BHAG (Big Hairy Audacious Goal) my way, I’m all in. There’s something thrilling about a challenge that makes my adrenaline spike—even if I don’t always show it. So, when a digital marketing opportunity with a startup DSO landed unexpectedly in my lap, there was no way I could say no. This was my second time working with a startup, and I knew the drill: you're building the plane mid-flight. You never really know where the ride will take you, but wow—this turned out to be one of the most exciting adventures of my career.Whether you're a fellow marketer gearing up for your own journey or just curious about the whirlwind of building a team, here are the lessons I learned—things I’d do again, and things I’d change if I had to start over.

1. Build a Team That Thrives Together

Your team is everything. I was lucky to have a mix of team members—some provided, some hired—and they became more than colleagues; they became friends. Building a great culture means finding people who work well together, especially when the waters get rough. This isn’t a solo mission. Having a team that shares the load and learns from each other makes all the difference.

2. Decide and Move Forward

When projects are flying in, indecision is your worst enemy. We started with nothing more than a massive whiteboard on wheels and sticky notes to map out our website projects and migration stages. It wasn’t fancy, but it worked—and fast. We’d snap a picture and post it on Teams so remote members could stay in the loop. Eventually, we transitioned to Smartsheets for online project management, but that trusty whiteboard stayed part of the workflow.

3. Listen. Ego Has No Place Here

Startups move too fast for egos. You need to listen—really listen—to your team. Every voice matters, and you’ll be surprised how much you can learn when everyone shares their insights. Collaboration isn't just a buzzword; it’s essential.

4. Appreciate Everyone’s Unique Strengths

Every person brings something special to the table. I had one team member who documented everything before any site redesign or migration. She was a lifesaver. When she left, we lost a lot of valuable insights. I only wish I’d organized that information better from the start so it was easier to access after she left. Lesson learned: don’t take anyone’s contributions for granted.

5. Communicate Like Your Success Depends on It (Because It Does)

There’s nothing worse than chasing moving goalposts with no idea where they’ve landed. In digital marketing, things shift constantly. You need crystal-clear, consistent communication. Daily 15-minute check-ins were a game-changer for us. They reminded us we were a team, always ready to help each other out.

6. Celebrate the Wins, Big and Small

I struggle with this one. I’m always chasing the next goal, but celebrating wins is vital. My boss was great at this, and I’m still learning from him. One of our most memorable celebrations was a farewell lunch at… Costco. Yep, Costco hot dogs—cheap, greasy, and ridiculously fun. It wasn’t fancy, but it was exactly what we needed: a reminder to enjoy the little things and not take ourselves too seriously.

7. Build Relationships Across Departments

Marketing doesn’t operate in a bubble. To succeed, you need strong relationships with IT, operations, doctors, and office managers. One of my biggest wins was having a paid ads manager who built great relationships with our stakeholders. My regret? Not setting up regular communication about site traffic and leads with the doctors. It was a matter of bandwidth, but I wish I had pushed for that from the start.

8. Install a CRM - ASAP!

If I could go back in time, this would be my number-one priority. Without a CRM, it’s tough to prove the value of your marketing efforts. I was so focused on migrating sites and setting up processes that I delayed pushing for a CRM—and by the time we got one, it was too late to show our early impact. Don’t make this mistake. Marketing and sales need to be on the same page from day one, and a CRM bridges that gap.

9. Send Reports, Even When They Aren’t Pretty

We avoided sending monthly reports at first—partly due to fear of showing bad numbers and partly because we lacked the resources to go over them with every office. Instead, we did quarterly reports. Looking back, even imperfect reports are better than none. They show you care, keep communication open, and give you a chance to fix issues before they grow. Transparency builds trust, even when the news isn’t great.

10. Tune Out the Naysayers

If I had listened to every skeptic, I would have walked away. People have their own agendas - always remember that. One stakeholder once told me that website leads had little value. If I hadn’t known better, I might have believed him. But I’d seen firsthand how leads from digital channels transform businesses. Not everyone will understand your process or see the value right away—and that’s okay. Stick to what you know.

Summary

Acquiring 100 dental websites in a year was no small feat. It was a wild, challenging, and deeply rewarding experience that taught me invaluable lessons about teamwork, communication, and persistence. If you find yourself in a similar situation—whether it’s migrating websites, scaling a digital team, or tackling a startup project—lean into the chaos, trust your team, and don’t forget to celebrate along the way.Because sometimes, the best adventures aren’t the ones you plan—they’re the ones you build as you go.