Last updated at Fri, 27 May 2022 14:13:25 GMT

Sales roles are all about people. That holds true not only when you're building relationships with prospects but also in your day-to-day experience on the team. Having the right culture and people around you can make or break your success, satisfaction, and long-term growth. If you're a job seeker looking for a technology sales role, getting to know the people you'd be working with can help you understand if that company is a place you can flourish and advance your career to the next level.

We asked two experienced sales leaders — Dan Bidwell, Regional Vice President - Central; and Jason Doris, Regional Vice President - East — who recently joined Rapid7 to tell us a little bit about themselves, what's most exciting about being on their teams, and why they chose Rapid7 as the next step in their professional journeys.

What was your background prior to coming to Rapid7?

Dan: I have had a lengthy career selling enterprise technology solutions for both large high-tech providers and startups. My career started with companies like NCR, Sun Microsystems, and Oracle. I left Oracle to pursue a path of working with early-stage startup companies such as Portal Software, Arcsight, Veracode, and Illumio. I enjoyed the cybersecurity space, and once I started, I never looked back.

Jason: After 25 years in the document capture and workflow industry, I transitioned to cybersecurity. I have an eclectic background, having sold in virtually every segment (enterprise, mid-market, consumer) and in every route to market (eCommerce, B2B direct and through the channel, OEM) including 14 years in global roles.

I am coming from Fastly, an edge computing cloud services company focused on website acceleration and web application and API protection. While there, I started a Financial Services vertical where we closed large deals with the likes of Goldman Sachs and PayPal. Most recently, as the RVP for the East, Fastly’s “Security First" strategy has helped take customers like HCA, Metlife, Foot Locker, and Assurant away from competitors like Akamai and Cloudflare.

How did you first find yourself in a sales role?

Dan: My first sales role was with NCR out of college. NCR provided two benefits — one, they had an extensive training program for people who had not sold high tech solutions. The second was that I worked for their Computer Systems Group, so I started selling both mini computers and manufacturing software from the beginning.

Jason: In college, I grew disenchanted as a Psychology major and changed my major to Business Administration late in the process. Directly out of college, I returned to the supermarkets that I worked in since I was 15 and entered the management trainee program. After rising to a department manager and experiencing 60-hour workweeks for 5 years, I took a chance on myself by entering a sales career. I believed that with my work ethic and lessons learned in a false start in grocery, and given a chance and a fair set of rules, that betting on myself would pay off — and it has.

How would others on your team describe you as a leader?

Dan: I strive to be a leader who is hands-on and works closely with his team. This is not code for micro management but rather being another member of the team who is there to assist and add value in any way possible to advance the cause. No job is too big or too small to help with.

Jason: I believe that my team would say that I lead from the front and by example, that I take the profession of sales seriously, that I am grounded and transparent, and that I am a positive, optimistic influence.

How do you define and measure success?

Dan: In sales, success is ultimately defined by quota achievement. But quota achievement cannot be attained unless you build and enable a team of sellers who have a passion and a belief in both the solution they are selling, and their customer's success and satisfaction with that solution.

Jason: I see success as achieving goals on one's career arc and personal financial goals arc, while positively contributing to a company's team selling culture.

What has surprised you or changed your ideas about what it means to be in sales?

Dan: If you observe sales from the outside, you may feel it's about the individual, but the reality is that it's about the team.

Jason: Mature athletes at the highest levels often refer to the game “slowing down" for them as they gained experience and became more successful. Despite what I would have initially believed, this is exactly what I have experienced: I started out selling on adrenalin and threw myself at my customers and prospects. Since then, I've planned my attack, listened more, had more opportunities sought the advice of others, practiced conversations, surrounded myself with smart people, and focused on the needs of customers.

What do you think are the most important elements of a successful, thriving sales team

Dan: The team needs to understand that you cannot go it alone. It can take a village to land a deal. Don't be afraid to ask for help. Ask early, and ask often. And be willing to offer help to your teammates, as well.

Jason: Curiosity, creativity, energy, resourcefulness, resilience, and a willingness to bet on oneself.

What made you choose Rapid7 for this chapter in your career?

Dan: I have admired what Rapid7 has done and I am excited about where they are going in the future. I believe they have the right solutions at the right time. Rapid7 has a great culture, strong executive leadership and the company is financially strong.

Jason: I was looking for an important role at a growing security software provider with deep enterprise aspirations and a great culture. At Rapid7, what I found is an expanding portfolio with a high cross-sell ceiling and engaging conversation with everyone I've met. In our transition — largely from a mid-market, one- to two-product selling motion to that of an enterprise portfolio or platform company — the need for developing deep relationships with customers and the channel is key, and that's something I enjoy and can help with.

What's ahead for your sales teams at Rapid7? What kinds of opportunities and experiences can those who join expect?

Dan: What is ahead is an exciting ride. There will be plenty of challenges, victories, and fun. I expect we will build relationships that will last a lifetime.

Jason: Rapid7 is growing rapidly while learning to be more efficient at scale. We are not opportunity-constrained in the market, and we rely on a balanced approach — both landing new customers and expanding the ones we have. Sellers can expect to learn a diverse strategic approach from peers while given the freedom to develop and apply their best ideas.

Why should those looking to start or grow in sales roles bring their talents to Rapid7?

Dan: Rapid7 is a great place to learn, grow, and flourish. I can't think of a better company to start and evolve your technology career.

Jason: Diversity in experiences, an excellent selling culture, and great technology. We also have stakeholders who are willing and able to help, as well as generous awards for those who succeed.

As you think about the year ahead in your role and at Rapid7, what are you most excited for?

Dan: Success!! As mentioned before, I believe we have the right products for us to meet and exceed our customer’s needs, and this is an exciting time where cybersecurity has become more of a “must have” than a “nice to have” for companies across all industries. I look forward to leading my team through the many wins and inevitable learning opportunities that are before us.

Jason: Learning, growing, and digging deep. Learning how to apply the benefits of our technology on the most important customer needs and challenges. Growing as a leader by surrounding myself with smart and ambitious sellers and applying the best suggestions early and often. Digging deep by immersing myself in customer and partner relationships.

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