From comfort to challenge: Angela Karl’s midwest playbook for building high-impact teams

Real growth starts at the edge of your comfort zone. For Angela Karl, that meant joining Smartsheet as a Senior Regional Director and building everything from the ground up. A new product to learn, a blank territory, and a big opportunity to shape what’s next.

Fast forward a year later, and the team she’s built is thriving–tight-knit, high-performing, and setting a new standard for enterprise sales in the Midwest. We sat down with Angela to learn how she’s grown a team that’s fearless in the field, thoughtful in strategy, and genuinely invested in one another’s success. 

Tell us a little about your background. What brought you to Smartsheet?

I’ve been in sales for almost 20 years—mostly in SaaS, and across a range of industries. Over time, I realized I was craving a new kind of challenge, something that would push me to think differently and give me the chance to build again.

What drew me to Smartsheet was a combination of the opportunity and the people. I had worked with several folks here in the past and had a lot of trust and respect for them. That made the decision to jump in much easier.

What was it like stepping into a brand-new region?

It was exciting—and honestly, a little intimidating. I was walking into something brand new: no team, no existing structure, a new product to learn. But that’s what made it compelling, I love building. There’s something really rewarding about putting the pieces together yourself and seeing it start to click.

Now, a year in, we’ve built something special. The team has gelled, we’re gaining momentum, and we’ve created a culture that people want to be part of.

What’s your vision for enterprise sales at Smartsheet?

We’ve got a strong transactional foundation, but we’re raising the bar. The vision is about going deeper—elevating the conversation, expanding across departments, and becoming true strategic partners.

That mindset has shaped how I hire. I look for people who are fearless in the account but also thoughtful, people who can land big but then expand with purpose. You have to be able to look around corners, think a few steps ahead, and understand how a deal can grow over time.

How would you describe the culture you’ve built?

Intentional. Collaborative. High-performing.

I’ve been really thoughtful about how we build the team—skills, backgrounds, perspectives. I’m not looking for clones. I want people who bring something different to the table but share the same values.

We challenge each other. We support each other. We enjoy the work. There’s a strong sense of trust and momentum, and that’s something we’ve built together from day one.

What do you look for in candidates?

It’s not just what’s on your resume. I care about the intangibles—curiosity, adaptability, strategic thinking. Those are the qualities that set great reps apart.

I want people who know how to think through a deal, how to build meaningful relationships inside an account, and how to pivot when things shift. You’ve got to be able to zoom in and zoom out—connect the dots across an organization while still delivering in the moment. This region is full of opportunity, and we’re in build mode. If you want to join a team that’s collaborative, ambitious, and focused on doing things the right way, this is the place.

Thank you to Angela and her team for reminding us that growth begins when we lean into challenges. Their story is proof that when you build with purpose, invest in people, and stay curious, great things happen. They’re helping shape the future of sales at Smartsheet: one account, breakthrough, and hire at a time.

Think you’ve got what it takes to join a team that’s raising the bar? Explore open roles on our Enterprise Sales teams.