ian "easy" crew - SaaS Sales & Growth Expert

Ian “Easy” Crew

If there’s one thing I’ve learned over the years, it’s that growth, real meaningful long-term growth, comes from relationships. Not gimmicks, not shortcuts, not pressure tactics. Relationships. I’ve built my entire career on that belief, and honestly, it’s the one thing that’s never steered me wrong.

My name is Easy, and I’m a consultative salesperson through and through. I’m someone who genuinely enjoys walking into complex situations, rolling up my sleeves, and helping people solve real problems. Whether that’s untangling outdated operations, introducing smarter technology, or helping a business understand how to scale without losing its identity. I’ve spent the last decade in SaaS, cannabis tech, start-ups, field operations, and even hands-on small business transformations, and every step of the way I’ve stayed rooted in the same approach: you can't fake caring, folks can smell that a mile away!

A lot of people know me from GrasshopperHub, where I helped build the company from literally nothing. No playbook, no brand, no customer base, just a vision, a crazy work ethic, and a willingness to talk to anybody who’d give me a shot. We grew that thing brick by brick until it became valuable enough to be acquired. That experience taught me more than any book or training ever could: how to wear every hat, how to hear “no” a thousand times and keep going, and how to create momentum from scratch.

For over a decade now I have worked in one of the toughest and fastest-moving verticals out there: cannabis SaaS. I spent years with GrasshopperHub, Cova, and Weedmaps helping dispensaries and brands modernize their tech stacks, drive new customers through their doors, and compete in markets where the rules changed daily. The Northeast in particular became a big part of my story. I helped introduce on and off platform marketing to that region, built real partnerships out there, and hit retention numbers I’ll always be proud of. (There’s something special about helping a small business owner grow their whole livelihood, it hits differently)

I’ve always gravitated toward businesses that are rough around the edges or stuck in old patterns. One of my favorite accomplishments was helping Wiseman Appliance go from the stone-age world of Post-its, paper trails, and verbal processes to a streamlined, tech driven system where everyone finally had visibility and structure. It wasn’t glamorous, but it was real transformation. Step by step, person by person, building trust and then building systems.

Across all of these roles, I’ve stayed the same type of salesperson. The guy who knows how to talk to anyone, who isn’t afraid of walking into uncertainty, and who can make complicated tools feel simple for people who are busy just running their business. I’ve never been the “pushy” type, I’m the “let’s work through this together” type. I ask a lot of questions, I make sure I actually understand the problem, and I don’t disappear after the contract is signed. That’s just not my style.

On the personal side, sports shaped a lot of who I am. I grew up competing in baseball and basketball then basketball and tennis in high school. Then later golf and ultimate frisbee in the Army leading to the last 20+ years of ball and disc golf. Sports taught me discipline, resilience, and how to be coachable. They taught me how to perform under pressure and how to stay calm when everything is on the line. Those lessons show up in my sales career every single day like consistency, preparation, teamwork, and knowing how to win without needing to act like you’re winning.

Today, I’m continuing to build my career around SaaS, growth, relationship driven selling, and helping companies modernize their revenue engine. Whether I’m advising, selling, managing accounts, or building something new, my goal stays the same, help the people in front of me succeed. If you can nail that, everything else like ARR, retention, adoption, and expansion all follows naturally.

This site is a collection of my work, my story, my style, and the way I approach building value through genuine connection. If you’re here because you’re curious about working together, partnering on a project, or just exploring what I bring to the table.... welcome. Take your time, look around, and reach out if something resonates.

You can't fake caring, folks can smell that a mile away.