Midwest momentum: What fuels a dynamic Smartsheet sales team

Sales leadership isn’t just about setting direction — it’s about setting the tone. For Anthony Trupiano, Senior Regional Director, Enterprise, that tone is clear: be real, work hard, win together. He’s leading with intention, building with purpose, and proving that when values lead, results follow.

What’s your background and role at Smartsheet? 

I’ve spent most of my career in software sales. I’ve been at Smartsheet for three years now — starting on the Strategic Enterprise team and now leading our Enterprise region in the Midwest.

From the beginning, I was clear that I wanted to grow into leadership. I focused on high performance and tried to model the kind of leadership I admired. I was lucky to have leaders who supported me, and now I get to pay that forward by building and leading an incredible team.

What made you confident that Smartsheet was the next step for you? 

The people and the product. A former colleague encouraged me to apply, and everything during the interview process just clicked. I saw an opportunity to grow, but also a product that inspired me.

What stood out most was the balance of autonomy and support. I knew I could step in, deliver results, and be trusted to do what I do best.

How would you describe your leadership style? 

I lead with humility and clarity. I want my team to feel confident in what they’re doing, but also know that I’ve got their back. I’m in the battle with them, but then I’ll also go to battle for them if needed.

I’m passionate about developing people, whether that’s coaching through tough deals, helping prepare for high-stakes meetings, or providing resources to grow. I have five pillars I’m really focused on for my team — transparency, teamwork, buy-in, growth (professional development and revenue), and ownership. These reflect both my values and our team’s strengths.

What’s something unique about your team?

We’ve got a great mix of experience levels and personalities, and we’re still growing. The Midwest market has huge potential — we’re just getting started. Plus, we benefit from an incredible extended ecosystem. Our Solutions Engineers and cross-functional partners are world-class.

But what really sets us apart is how we show up for each other. It’s not a “me-first” team. We share, we support, we celebrate together — and we make it fun.

What growth opportunities can someone expect?

There’s a ton of opportunity. We’re growing fast, and that means new team members can carve out their identity quickly and build long-term success.

What’s exciting about our roles is the variety. You might go from a conversation with procurement to marketing to mergers and acquisitions — all in a single week. You’re exposed to different departments and decision-makers, which challenges you to grow quickly and think strategically.

What do you look for when you’re hiring? 

Enterprise sales experience is key. I want to hear how you approach complex accounts, uncover business pain to find impactful solutions, and build relationships across organizations. But coachability and being a team player matter just as much. You don’t need to sell like everyone else, but you do need to row in the same direction. If you’re looking to level up your career during a high-growth moment for the business, you’ll find success here.

Thanks to Anthony and his team for showing us that leading through intention, trust, and a willingness to jump in and get things done drives more than individual results. Their story is a reminder that when you invest in people and create space for growth, great things happen.

As the Midwest region continues to grow and scale, so do our career opportunities. If you want to grow and win with an innovative team, check out our open roles.