Our Fireside Fridays series is where we have the opportunity to sit down with top B2B revenue leaders for 7 questions and get a behind-the-scenes look at their recommended best practices, their background, and factors that have contributed to their success.  This is our interview with Rocky Paap, VP Revenue and WorkRamp.

Give us your background in sales

I’ve held various roles within high-growth SaaS companies (SuccessFactors, Box, Blackbird, Periscope Data, Envoy WorkRamp) ranging from Sales Development, Account Management, Account Executive, Sales Manager, Director of Sales, VP Sales to VP Revenue. I was a member of Box’s original sales team (circa 2009) and closed several of the first 6 figure deals in the company’s history. After being promoted to be one of the company’s first sales managers I helped hire and scale a materially significant portion of the sales team while helping develop the foundation of the sales process, go-to-market, and sales operations. I got here by getting lucky and working hard. Worked at companies that trained me well, gave me opportunities to grow and I had excellent mentors (Jerry Clarno, Jim Herbold).

What’s both your personal, and professional, superpower?

My superpower is probably equal parts empathy, being unafraid of taking risks, and never giving up. I fail a lot but always try to pick myself back up, learn something from it and try something new. The empathy comes into play as far as trying to understand where others are coming from and seeing myself in their shoes. You can learn a lot by stepping away from your own goals and understand theirs. Then seeking alignment.

What’s the best piece of sales or business advice you ever got, and from who?

Be curious and human. I learned curiosity from my grandmother Betty Paap. As a kid, whenever I asked a question she would point me to the large set of bookshelves she had and told me to go research and then come back and tell her the answer. This taught me that you can learn and improve by seeking out information. My first sales manager Art Rodich taught me about being human, On my first field sales day, he shadowed my pitches and told me to loosen up, be quirky, be myself. Talk to people like they are your friends instead of script-based and robotic.

What is the biggest challenge today facing a sales professional, and how would you recommend they overcome it?

The biggest challenge today for Salespeople is time management and focus. SaaS startups move at a breakneck pace. There are so many tools, so many competitors, so many launches, buyers have so much more information at their fingertips and so many ways of communicating. It can be overwhelming to know what to read, research, what messaging to keep track of, etc. I recommend they overcome it by first start networking with their most successful peers and learning from them. Recording tools like Gong and Chorus are also extremely helpful because they show you what types of styles there are and what is most important to know to succeed at your company. There are no silver bullets so learning and trying new things to see what works best for you is ideal.

What companies, brands, or influencers in the industry do you follow and/or respect most, and why?

Aaron Levie will always be the main one for me. His drive, sense of humor, creativity, and empathy is unique. He also has boundless energy and is generous with his time. Jason Lemkin, David Skok, Tomas Tunguz, are another few examples that pop into my head immediately. They share experience and information (many times based on data) freely and educate others on what it takes to succeed in SaaS.

What’s the best advice you’d give to someone just starting a career in sales or revenue overall within B2B tech?

My best advice is to network with everyone. Don’t be fake about it though. Be genuinely curious about what everyone does and what their goals are. First and foremost, having an understanding of how a business operates will pay dividends in your career. Secondly, you may need help with something, and the more people you know the more ideas and help you can get. Thirdly the world is smaller than you think and having a strong network will help you find the best opportunities and companies as you grow in your career.

Do you see any interesting future trends as it pertains to sales or B2B tech?

I see the B2B tech world becoming even more consumerized and competitive. It’s easier than ever to launch a company and compete. It’s also harder to keep customers because there are so many options and ways for new companies to come into a space and take what you do best, start there, and then iterate from the beginning vs slowly finding their way there. This is GREAT for buyers because more transparency and options means better service, SaaS companies that will succeed need to focus on customer experience vs snazzy marketing and high-pressure sales tactics. Deliver real value.
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