00:00
Bryan Schielke: Shelly, you've led companies from early stage all the way to enterprise scale. What's the most surprising lesson you've learned about growth along the way?

00:07
Shelly Freeman:
It’s all hard — and it all takes longer than you think it’s going to take. In a smaller company, the wins are different. Maybe it’s one big customer and it’s a huge win. At a larger company, you need ten customers to get that same win.

Even when you’ve got more resources and more people, it’s still hard — and it still takes longer than you expect. As I’ve gotten further into my career, I also believe there’s a little bit of luck involved. The stars have to align. You have to be ready internally, your customer has to be ready, and the environment has to be ready — like during COVID or the rise of AI.

You have to keep trying until all those pieces align.

00:59
Bryan Schielke: Building high-performance teams is central to your leadership. How do you identify and nurture leaders within your organization?

01:09
Shelly Freeman:
You can usually spot leaders pretty quickly. They’re the people others trust. They’re the ones teammates go to for guidance and answers.

Interestingly, they’re often the quieter people — not always the most outspoken. But they’ve earned trust from both the team and customers.

Once you identify them, you can grow them into leadership roles. It all comes back to trust — earning it, recognizing it, and nurturing it.

01:44
Bryan Schielke: In your experience, what is the single biggest factor in turning underperforming teams into high-performing teams?

01:53
Shelly Freeman:
Making tough decisions.

I’ve seen it both ways. You have to identify who’s not pulling their weight. They may be wonderful people — everyone may love them — but if they’re not performing, you have to make hard calls.

High-performing teams require everyone giving 110%. It’s not about just having nice people. It’s about having accountable, high-performing contributors aligned toward the same goal.

It’s really hard to do — but it’s necessary.

02:35
Bryan Schielke: Customer-centric strategy is core to your work. Can you share a moment where a customer insight changed the direction of a business?

02:45
Shelly Freeman:
Earlier in my career, especially in SaaS, we tried to stay two steps ahead of customers with long product roadmaps.

Over time, we shifted. Instead of trying to anticipate everything, we started listening more. Sitting with customers. Watching how they used our software. Gathering real feedback.

That changed everything.

We moved from rigid, long-term roadmaps to a more agile approach — adjusting based on real customer usage and input. Being flexible and customer-driven made a massive difference.

03:45
Bryan Schielke: You’ve guided companies through acquisitions. What’s one operational or cultural challenge that is often underestimated during that process?

03:57
Shelly Freeman:
Culture — especially across locations.

I once helped combine a Seattle office with a New York office. The intensity levels were completely different. By 9 a.m. in Seattle, our New York team had already commuted by subway, ferry, train — their day felt intense before ours even started.

You have to acknowledge those environmental and cultural differences.

I’ve also worked internationally — including Australia and the Middle East — and every region has unique dynamics. You must understand them, respect them, and find common ground so everyone can align around shared goals.

05:01
Bryan Schielke: Scaling AI and SaaS companies globally requires balancing technology and people. How do you ensure both sides thrive?

05:13
Shelly Freeman:
From a technology standpoint, scaling globally is easier than ever. Cloud infrastructure and language tools make expansion seamless.

The hard part is people.

You have to understand cultural differences and working environments. I’ve worked in the Middle East, and as a woman, that came with unique dynamics. Acknowledging differences — not ignoring them — is critical.

The key is aligning around a common goal. Most often, that’s the customer. When everyone focuses on delivering value to customers, it becomes easier to bridge cultural differences and work together effectively.