The realistic optimist leading the next big move at Smartsheet

Justin Dobson is both a visionary and a realist — an unlikely combo. Through three decades in sales leadership, he stays focused on what matters: people, progress, and a healthy dose of optimism. As Regional Vice President of Sales in EMEA at Smartsheet, Justin is scaling a team that’s as focused on trust and ownership as it is on outcomes. 

What led you to Smartsheet?

My career has been a winding path, but an intentional one. Every role gave me a different perspective: how to grow a region, how to navigate complexity, how to lead global teams.

When Smartsheet came on my radar, I wasn’t actively looking, but I had quite a few interesting conversations that made it click. The people I met were sharp, thoughtful, and genuinely passionate about what they were doing. The culture felt grounded, and the opportunity in EMEA was exciting. It felt like a place where I could build something meaningful and have fun doing it.

You’ve called yourself a “realistic optimist.” What does that look like?

It’s in my DNA! I naturally look at the good first — but do so with open eyes. I believe challenges are solvable. That mindset has shaped how I lead. You can’t build great teams if you’re solely focused on what’s broken, you must also spotlight what’s working, and build on that. 

To me, leadership is about setting direction, but also helping people see what’s possible. Especially in a region like EMEA, where there’s so much growth potential, that mindset goes a long way.

Read more about Justin’s realistic optimism.

What excited you about the role in EMEA?

EMEA is such a dynamic region — it’s full of opportunity, but demands nuance. That complexity energizes me. Our team understands the market, trusts one another, and can pivot when needed. That’s what I love about this role. It’s not just about leading a team, it’s about building a culture that balances performance with people, and clarity with creativity.

What’s your leadership style like, and how has it shaped the culture of your team?

I lead with trust and transparency. I believe in setting clear expectations and then giving people the space to deliver. Micromanagement doesn’t build great teams, empowerment does. 

That said, I’m highly present. I want to know how the team is doing, both in their work and in life. Sales can be tough and fast-paced, but also incredibly fulfilling if you have the right support. I want people to feel like they can take risks, speak up, and grow. That’s where the magic happens.

What kind of candidate thrives on your team?

Someone who’s curious and thoughtful. Someone who doesn’t need every answer upfront but has the drive and knowledge to figure it out. We work in an emerging space, and sometimes customers don’t even know what’s possible with Smartsheet until we show them. 

I look for people who can connect the dots, ask the right questions, and get excited about solving problems. And of course, someone who thrives when working across a diverse and evolving region. 

Thank you to Justin for sharing his perspective on building with heart and leading with intention. From navigating complexity to creating space for people to thrive, his approach to leadership is one that helps teams, and individuals, grow stronger together.

Interested in joining our growing teams? Explore open roles and help shape the future with us.