“Why I’m So Interested In Selling,” Cassi Roper

Preface: I met Cassi Roper a number of years ago. She ran EMEA Strategic Accounts for Redgate Software. She learned I was working with the North American teams in changing their approach to their markets and driving more aggressive sales growth. Curious, she came to the US to participate in strategy and other workshops, adapting what we were putting in place to her strategies in EMEA. We later looked at methods to ratchet up performance even further. Over the years she took more responsibility and is now the CRO.

Cassi highlights a key issue many others have alluded to. There has, often, been a stigma associated with sales people, nurtured by movies like Boiler Room and GLengarry Glen Ross. In Europe, the stigma with sales is, often, greater.

But it’s changing for the positive, as Cassi states, “I feel very strongly about ethical selling and the way in which we sell, sticking to our core values and treating the customer with respect.”

Why I’m so interested in selling: Cassi Roper, CRO, Redgate

How did you find yourself in a selling role?

My dad ran his own company when I was growing up, and he did a lot of selling to support his business. When I was younger, I used to go with him when he visited customers to give them quotes and collect their payments. He’s a natural relationship-builder, and I got that from him. I knew early on that I wanted to work with people, in a job that gave me opportunities to talk to them and help them solve their problems.

When I finished university, I wanted to find a job that paid well so that I could clear my student debt, while also giving me opportunities to build strong relationships with customers. My dream was to work in technology sales, but I didn’t have any experience of either technology or sales, so I got a job at a gym selling memberships.

I didn’t have any experience of working at a gym either, but I didn’t need any. I wanted to learn the fundamentals of sales, and I was lucky to get the chance to work with a strong business development manager, who taught me the art of asking great questions and the foundational elements of how to sell. Those foundations gave me enough selling experience to pivot into tech.

What’s your experience been as you’ve grown in your career?

When I started my career, sales wasn’t seen as a real career prospect. There was a stigma around selling and a lot of stereotypes, and it was worse in the UK (where I’m based) compared to the US. Ethical selling wasn’t part of the conversation. And when I first moved into tech, the software industry didn’t have a lot of expertise in selling – there weren’t many people to learn from, or examples of companies doing it really well.

Over the past five years, there’s been a rapid professionalisation of technology sales. The amount of tech companies spinning up a sales team has been significant, and it’s normal now for startups to begin doing business with a strong sales team and sales momentum. This has given the industry more weight, and it also means that there are a lot more educational opportunities and resources out there. There are even organisations like the Institute of Sales Professionals that offer professional sales qualifications.

As the software industry has grown, so has the reputation of sellers in the industry. It’s seen as a much more reputable and better-paid career path compared to when I was starting out, and it’s viewed much more positively than it once was.

Why do you stay in selling?

Because I’m still really interested in solving customers’ problems. It’s almost like being a doctor – if you ask the right questions you can build an appropriate diagnosis, and then help the customer apply the cure. It’s all about understanding their pain points, and my interest in doing that hasn’t changed during my career.

I also love helping people go on the same journey I’ve been on, either turning them from entry level into amazing sales people, or supporting them to develop down the management track. I find it very motivating.

And I feel very strongly about ethical selling and the way in which we sell, sticking to our core values and treating the customer with respect.

What would you tell someone considering a career in sales?

Master the art of asking great questions and listening to the answers. If you can do that, you’ll always have a fantastic career in sales.

Find a great mentor to help you throughout your career journey, and soak up the learning – there’s so much information and so many resources out there now to help you grow as a sales professional.

And if you’re in a technical sales role, don’t be too intimidated by your product. Your customers will always be experts in the space and might have more technical knowledge than you ever will. But just like you don’t need to be a doctor to sell medical equipment, you don’t need to be a software engineer to sell software solutions. Have faith in yourself that you can learn as much as you need to know to be able to sell your product effectively.