Matt Rosenberg didn’t predict a career in sales. After earning his law degree and working as a corporate attorney, he realized the law profession wasn’t for him. Twenty years ago, he was offered an opportunity to head up business development at a brand-new startup. He took the leap of faith, discovered his true passion in sales, and never looked back. Now as chief revenue officer at Eventbrite, an event technology platform which processes over 2 million tickets and registrations per week to events in more than 180 countries, Rosenberg oversees a diverse team that includes both sales and marketing.
Here Rosenberg shares how he found his passion in sales and why rallying teams around a mission and their passion — and not just numbers — will create a successful sales organization.

I graduated Northwestern Law School and went to a corporate law firm in Chicago. I absolutely didn't like it, and I was frustrated by the boundary conditions of being a lawyer. It was very isolating.

When I accepted a position for business development, I soon found that sales is one of the most complex, challenging, and interesting things I’d ever done. I had a knack for it and I enjoyed it. I fell in love with the intellectual and emotional challenges, the competitive aspect of it, and listening to customer needs and figuring out how to solve them within a product or solution. It’s safe to say it was love at first sight with sales. For my next job I went on to become a sales manager and my career went from there.

As a young lawyer, I mainly did a lot of research, brief writing, due diligence, and review of contracts. Juxtapose that against sales where it’s a team from different parts of the organization coming together to solve a problem. It’s inherently much more engaging and interpersonal. You have product, engineering, design, marketing, and sales teams — it really is a team sport when done at its best.
Being a lawyer is really about listening very carefully to your client’s problem because there is a good deal of nuance with law. When you bring that into sales, it’s the same thing. A customer may think they’re solving for one thing, but when you dig a couple layers deeper, they’re actually solving for something else. To the extent you can understand this and how it ties back to their organizational and personal goals, that’s when you win.
Many people think about sales as being social because you’re often at the bar, golf course, or out socially with clients. But I think great sellers thrive in a different kind of social engagement. It’s in the context of a business problem, engaging in a board room or around the table. When I look for sales people I actually look for people that possess those attributes where they can be “social animals” in the business context. Those who are serious about their business will be more successful than people just trying to win on personality or other aspects of sales.
When you’re running a large sales organization the hardest thing is getting everyone aligned behind the goal. Goals are targets you have, but that’s not the alignment you need to drive. It’s the bigger mission, values, and how sales fits into the company and its culture. If the sales team believes it’s doing something valuable for the business, industry, or consumer, you tend to win a lot more frequently than sales leaders who try to rally their team around the number. The number is a byproduct. You’ll get there if everyone is engaged with what you’re doing. But getting everyone focused on that bigger mission and believing in it is always the most important and hardest starting place.

One of my biggest jobs as a sales leader is to retain our team members that we have invested in and identified as top talent. I want them to pick up the recruiter calls, but be so inspired by what they're doing at Eventbrite and fulfilled with their career path that they never actually move forward in those calls.

What holds people to organizations is a fundamental belief that they’re part of something bigger than themselves. All too often, sales leaders don’t spend enough time focusing on what motivates their employees. Sales is a brutally hard job — getting rejected and putting yourself out there, day in and day out. If you had a 50% success rate in sales, that’s an amazing success rate, but it means you’re failing half the time. If you’re not aligned behind that greater mission of the business, then the only thing keeping a sales rep is the W–2, and that becomes hollow after a while.

I think first and foremost it drives better performance. You have one life, follow a passion. It doesn’t matter what your passion is, just follow it. I think it’s no different in sales.

People that perform well because they believe in the mission naturally inspire others. They take on those leadership properties because they’re aligned to the culture and mission of the business. And this sets them up to move quickly within the organization because they’re viewed as high performing, understand the mission and the culture, and will continue to drive growth. That’s a natural candidate to step into a leadership role.

I look for really high IQ and EQ folks who are genuinely inquisitive, understand people, and are willing to have fair and balanced discussions with their team. All too often, you find sales managers who want to either be liked or manage with too heavy a hand. There’s a balance in how to do this.

One of the most important hires is the sales-management layer of the organization because people go to work for people. At the end of the day, I could deliver the greatest mission and vision for the organization, but if I'm putting in place the wrong leadership, no one is going to stick around.

I’d like to be a general manager of a sports team. I believe the Chicago Bears could use a guy like me.
I’d say my closing song is “Lose Yourself” by Eminem.

I fell in love with the intellectual and emotional challenges; the competitive aspect of it; and listening to customer needs and figuring out how to solve them within a product or solution.”

Matt Rosenberg | CRO, Eventbrite
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