Jason Pelland

Background

About Jason Pelland

I’m a customer-obsessed revenue leader with over 8 years of experience building and leading high-performing sales and customer success teams and more than 20 years working across service, sales, and customer experience. I’ve launched business development departments from scratch, scaled SMB and retention teams nationally, led strategic customer experience overhauls, and implemented systems like Salesforce to streamline operations - all while keeping customers at the center of everything I do. My leadership style is rooted in empathy, clarity, and a deep commitment to ongoing learning; both for myself and my team. I don’t just lead to hit numbers; I lead to build strong, motivated humans who know how to show up, grow, and raise the bar for themselves and others. I’ve learned that culture isn’t built overnight - it’s built through small, consistent habits, clear standards, and genuine connection. I create environments where people feel safe to ask questions, challenge the status quo, and experiment without fear of failure. Coaching, to me, isn’t a one-time conversation, it’s embedded in the way we think, operate, and learn from every win and every mistake. I’m big on clarity: everyone knows what good looks like, what’s expected, and how to get better every single day. What makes me different? I don’t rely on playbooks. I build them. I’ve scaled teams from the ground up, redefined broken processes, and created systems where people thrive. I’m part strategist, part builder, part coach. And I lead with heart, because when people feel supported, valued, and challenged, they show up at their best. That’s when the magic happens, and that’s where I’ve seen my teams deliver extraordinary results. Outside of work, I love staying active and curious. I’m a former varsity water polo player and competitive swimmer, and these days you’ll find me at the gym, out for walks, camping, or battling it out on the golf course. Golf and I have had a complicated relationship - lots of heartbreak, a few great moments, and just enough progress to keep me coming back! Travel is a big part of who I am. Whether it’s exploring a new small town on a spontaneous road trip or immersing myself in a different culture halfway across the world, I find travel fuels my curiosity and perspective. At home, I love to wind down with a great meal (I love to cook), a good book, or anything that helps me learn something new. Let’s connect! Whether it’s to talk CX strategy, scaling teams, your travel bucket list, or the heartbreak of three-putting from six feet.